Majorly Instagrammable estates, world-class culinary hotspots, a relatively mild year-round climate, luxury spas, and, duh, the wine. Obviously. Napa has it all and is a dream destination that we could never get enough of. Whether you’re traveling for a minimoon, bachelorette party, birthday celebration or just a weekend getaway, Napa is the ideal destination for any occasion and with any combination of travel partners. As obsessed as we are with Napa, it does take a little bit more planning and research than your average domestic weekend trip and isn’t one that we’d recommend doing on a tight budget—although it can be done. Read on for all of our tips, tricks, and recs for pulling off the perfect Napa trip. Cheers!
A NOTE ON COVID-19:
If you do choose to travel right now, it is important to do so as safely and responsibly as possible. A few notes about how Napa in particular is managing the pandemic.
Napa and Sonoma counties have a mask mandate in place, and a mask should be worn in all public areas, except when eating and drinking. This includes when walking outdoors any time that 6 feet of distance cannot be maintained. We would suggest continuing to wear your mask when your server comes to your table as well. Wearing a mask primarily protects the other person and it’s important to show your server the same respect and caution that they are showing you.
All restaurants and wineries must operate exclusively outside at this time. This may change your experience slightly. For example, you may not be able to partake in all of the standard tours, such as any cave experiences or barrel tastings, but you will still have a wonderful time! In addition, your host may be less hands-on than normal in terms of walking you through the wine making process, tasting notes, etc.
From our experience, hotels were thoroughly sanitized and housekeeping services did not take place during a stay to minimize the number of people entering and exiting a room. In addition, efforts are being made at some hotels to allow a few days between guest stays in a particular room.
Lastly, we are advocates for taking any additional precautions that you can prior to traveling. While we did not have any symptoms, we tested both before and after our trip and quarantined while awaiting results each time. We recognize that we could be asymptomatic carriers.
Between the compounded effects of both COVID-19 and the recent wildfires, Napa Valley’s businesses need our support more than ever, but please visit as responsibly as you can!
How To Get There
If you live in the Bay Area, Napa is the perfect weekend destination! If not, you’ll most likely be flying to get to Napa. With three local airports, you have a lot of options depending on what your priority is—ease or price. No matter which airport you fly into, though, expect a bit of a drive.
If you’re looking to get as close as possible to wine country, you’ll want to fly directly into Santa Rosa (Sonoma County Airport). Flights here are less frequent, more expensive, and depending on where you choose to stay in wine country, could still require a 20-40 mile drive. One bonus of this airport, though, is that you can check up to a case of wine for free when you’re flying home! Love that.
For the average traveler, you’ll want to fly into SFO (San Francisco International Airport). As one of the busiest airports in the country, you’ll have no problem finding flight options and a great flight deal. Hello, more money for wine tastings! From SFO, you have about a 1 hour drive into Napa. We’d recommend either renting a car or, if you’re celebrating a bachelorette, renting a limo or party bus for the ride. Pro Tip: If you’re landing earlier in the day and choose to rent a car, take the Golden Gate into Sausalito on your way to Napa and stop off for a bite to eat or glass of wine with killer views of SF and the Bay.
Lastly, Oakland is a third option for flying into Napa. Technically, Oakland is a little bit closer to Napa than SFO, but could be more challenging to find flight deals depending on where you’re coming from. We recommend setting flight alerts on Google Flights and Hopper for all three airports (Santa Rosa, San Francisco, and Oakland) and booking whichever comes back as the best value between price, arrival/departure times, and flight route.
Where To Stay
One of the most common misconceptions when planning a Napa trip is that you want to stay in Napa proper. When most people say they want to go to Napa, they are referring to Napa Valley or the entire wine country of Napa and Sonoma counties. It is a HUGE area, and choosing which town or area to stay in is so important to a successful and enjoyable trip. We’ll break down the options, high-level, below:
Napa – As the biggest town in Napa Valley, Napa is the most lively area that you could stay with restaurants and bars within walking distance of one another, most of the larger hotel chains (Westin, Embassy Suites, Marriott, etc.) and is a pretty centrally located spot for whatever you choose to do in the area. Plus, the Napa River is a pretty cute spot to walk along.
Yountville to St. Helena – These towns are technically 10 miles apart (about 20 minutes), but for the ease of writing this guide, we’ll group these towns together (along with Oakville, Rutherford, and the other small towns between these two.) In our opinion, these towns are what people typically dream of or imagine when they think of wine country and visiting Napa. Slow-paced, romantic, a vineyard view from your room, etc. These towns are also where all of our favorite wineries and restaurants are located.
Calistoga – Calistoga is often considered the end (or beginning) of Napa Valley and offers a similar wine country feel to Yountville and St. Helena, but in a much quieter and relaxing way. Calistoga would be a perfect area to stay for a honeymoon or anniversary trip. Super charming, secluded, understated, and laidback.
Sonoma – Sonoma is technically in a completely different county, but we think it’s still worth mentioning when planning a Napa trip. Sonoma is, in our opinion, much less commercialized and touristy. Think of it like Napa’s laid-back little sister. Sonoma is an incredible place to visit and actually grows more grapes than Napa, and it’s a stunning area with some of the best Pinots in the world. We ultimately do prefer Napa Valley, but always say that Napa is not a trip to do on a tight budget. Sonoma can be a more affordable option for hotels, restaurants, tastings, and still a very fun place to visit.
There are so many insanely beautiful and luxurious hotels, resorts, and Airbnbs in the area. For the purpose of this guide, we would recommend Silverado Resort. While it’s not in the heart of any of Napa Valley’s towns, its location is central enough to allow you to plan activities in most of the spots around the valley. It’s an expansive and beautiful resort property with multiple pools, two golf courses, a spa, and plentiful restaurant options, all while being a surprisingly affordable option—by Napa standards, that is. For any Real Housewives super fans like us, the OC wives stayed at Silverado on their Napa trip (season 10, episode 3, to be exact). If it’s good enough for Heather Dubrow, it’s more than good enough for us.
How To Get Around
Unless you have a DD in your group (unlikely since you’re in wine country), we’d recommend hiring a driver for your day of wine tasting. Napa Valley is a huge area and the wineries stretch out along a highway, so walking just isn’t an option. Ubers and taxis are harder to come by and because Napa is a place where reservations are definitely required, you won’t want to waste any time between appointments waiting around for an Uber. If you’re traveling with a group, hiring a driver is actually very reasonable. Definitely plan ahead for this and don’t wait to figure it out upon arrival. Drinking and driving just isn’t the move.
Where To Eat
Our second favorite part of the guide! Napa Valley is a foodie mecca. So much work and research goes into pairing wine and food, so of course, in a world-famous wine region, there is no shortage of good food. Napa Valley is overflowing with some of the best chefs in the world ready to feed you after you’ve drunk your body weight in wine. It does, however, mean that many of the restaurants are at a slightly higher price point than you’re probably used to—we promise, they’re worth it!!
We recommend doing RH Wine Vault (yes, another of the highly Instagrammable concepts from Restoration Hardware) for pre-dinner drinks or wine tasting and then following up with dinner at Bistro Jeanty. They’re both in the heart of Yountville. RH Wine Vault has an incredibly Instagrammable aesthetic with string lights, outdoor couches, and a backdrop of a vine-covered building. Bistro Jeanty is all things French, and who doesn’t love some steak frites and cocktails with names like La Vie en Rose? You literally can’t go wrong, and they’re currently offering cocktails to go.
If you’re staying in Napa proper and love sushi, we’d recommend Morimoto in Napa. This will not be cheap, but it’s so worth it if you love sushi. You can sit inside or outside on the river, and the vibe is exactly what you want: very cool and modern. We’d stick with the sashimi and nigiri because the fish quality is so fresh. We’ve never had so much sushi delivered to us at once—a true dream. They also have great cocktails and an amazing wine list. There are a few locations around the world, so it’s not exclusive to Napa, but we still have to recommend it.
If you’re on your honeymoon or truly ready to ball out, The French Laundry is a must. We’ve never had the chance to eat here, but it is often regarded as one of the best restaurants in the world. A multiple course fixed menu with wine pairings for every course and each person has his/her own waiter. What we can only imagine to be a once in a lifetime experience.
Other wine country favorites include:
The Bistro at Auberge du Soleil – Perfect way to break up your day of wine tasting if you’re in the Rutherford/Yountville area. We could never afford to actually stay here, so lunching is the perfect alternative to get all of the chic French vibes at a fraction of the cost.
Farmstead Restaurant – A farm-to-table concept that somehow blends Southern comfort food with a signature light, fresh California flair.
Goose & Gander – A St. Helena staple famous for its burger and cocktails, as well as a signature Sunday brunch. Brunch runs from 11am-3pm, though, so it usually cuts into our wine tasting schedule. It’s a great option if brunch is your last plan on your way out of town on Sunday!
Ad Hoc & Addendum – Neighboring restaurants from Thomas Keller. Ad Hoc serves a renowned family style meal that changes daily. Addendum is famed for its legendary upscale fried chicken.
Oxbow Public Market – Centrally located near Napa proper, this is a great stop for groups with a variety of tastes or dietary needs. It’s an easy, casual spot to grab everything from Hog Island oysters to banh mi to pasta—with drinks, of course.
Where To Drink
Napa is all about the wine, so now let’s get to the good stuff! There are so many wineries in Napa Valley that you could visit every weekend for a year and still not hit them all. Here are our favorites to get good wine and a good ambience.
Del Dotto is one of those wineries that’s a can’t-miss. They have three tasting rooms, which makes it an easy stop no matter where you’re staying, but currently, only the Piazza is open due to COVID. You may recognize it from a recent KUWTK episode—Kylie’s first wine-tasting trip—but we’ve loved it before we were influenced by our favorite family. We highly recommend the barrel tasting (if you’re there during non-COVID times, you’ll actually get to taste from the barrel in their wine cellar). The tasting is $80 for 9 wines and includes a wood-fired pizza and tomato appetizer—a must to avoid getting white girl wasted.
For a casual lunch stop where you can still wine taste, V Sattui is a must. They offer a number of different types of wine tastings, and their marketplace and deli is full of yummy bites for lunch. Instead of doing a wine tasting here, you could also grab a few bottles from their marketplace and enjoy a picnic lunch. Honestly, the wine here is good (I mean, it’s Napa), but not out of this world. We stop here on every Napa visit though, because the food is good, easy, and convenient, and you don’t have to stop your wine tasting fun.
We are champagne and sparkling wine lovers, but, regardless, we always recommend the first tasting stop of your day to be for a sparkling tasting flight. We love wine, but 10am still feels a little aggressive to start exploring some bold cabs. Domaine Carneros is our favorite stop for this (you’ll feel like you’re actually in Champagne, France with the incredible tasting room) or Mumm Napa if you’re looking to taste some champagne that’s exclusive to the winery, and not what you’ll find at your local grocery store. For a bougier champagne experience, we recommend Schramsberg. Domaine Chandon is another option for sparkling that is super popular, but if you’re choosing between one or two options, it wouldn’t be our top choice.
For anyone staying in Sonoma, SIGH. is a must stop when you’re done with wine tastings, but not ready to end your day of drinking. A highly Instagrammable champagne bar. They’re currently set up in Sonoma Square due to COVID and offer a variety of frozen cocktails, their usual champagne offerings, as well as apps.
Other wine country faves:
HALL Wines – A must for any cab lovers in particular
Inglenook – Stunning property owned by Francis Ford Coppola
Castello di Amorosa – A literal castle
Artesa – Stunning, expansive views of Napa
Opus One – Luxurious experience, but with a somewhat more formal, exclusive vibe. Would not recommend this one for a bachelorette party.
Stag’s Leap – Iconic spot in Napa Valley that some would say put the region on the map in terms of international acclaim and respect.
Tips & Tricks For Planning A Successful Trip
Plan ahead!! Napa is absolutely a place that requires advanced planning. Make reservations for all the wineries and restaurants that you plan to visit. You may be able to just walk into some of the tasting rooms at the end of your day, but for the actual wineries and acclaimed restaurants, you absolutely need reservations and we’d recommend starting to book at least a month out.
MyMaps will be your best friend. When you first decide to plan a trip to Napa, you will be inundated with opinions and recommendations. There are just so many stellar spots. In the last two years alone, we’ve spent 13 days total in Napa and still feel like we’ve just scratched the surface. As you begin to compile all of your recs, plot them all on a map. See where things seem to naturally group together location-wise and plan each day around that. The towns can take a significant amount of time to travel between and, if you’re on a tight schedule, you will want to minimize your driving time.
Be realistic. We are obsessed with wine tasting and there are certainly some destinations in the country where it’s possible to squeeze six or seven tastings into a day if you’re ambitious. Napa is not one of those places. We wouldn’t recommend more than four tastings in a day. Most wineries open for tastings at 11 (10 if it’s sparkling wine) and most start their last tastings at 3:30 or 4. Plan for each tasting to last 60-90 minutes.
Budget accordingly! As we’ve mentioned several times, Napa is not a great place to do on a budget. Accommodations can be pricey, there are many world-renowned (aka expensive) restaurants, and the tastings are not cheap. Most of our previous wine tasting experiences were for tastings ranging from $15-30 with the tasting waived with the purchase of one bottle. In Napa, however, the average tasting fee is about $60 with some going well over $100, and the tastings are waived with the purchase of upwards of six bottles or joining a wine club. You can absolutely still visit Napa or Sonoma and find spots for less, but just know that it may not be the full wine country experience that you’ve imagined.
Perfect First Time Itinerary
Friday, Day 1
If you land in the morning/afternoon, drive over the Golden Gate + stop for lunch in Sausalito on your way to wine country.
If you land in the late afternoon/evening, head straight to RH Wine Vault for a tasting
Dinner at Bistro Jeanty
Cocktails to go + check into The Silverado Resort (or your accommodation of choice)
Saturday, Day 2
Breakfast at Bouchon Bakery (Expect a line here, but it’s worth it! You can easily take your food to go, so waiting to order is the longest part here).
Champagne Tasting at Mumm Napa (If you want to get in as many tastings as possible, book your tasting as soon as they open!)
Tasting at HALL Wines (You’ll have to skip this one if your champagne tasting starts any later than 10AM)
Lunch + Tasting at V Sattui
Tasting at Piazza Del Dotto
After changing and freshening up, grab pre-dinner cocktails at Sky & Vine Rooftop. If you’re running late, be sure to stop here after dinner!
Dinner at Morimoto
Sunday, Day 3 – Option A if you’re heading home on Sunday/just doing a weekend trip!
Brunch – Napa is famous for their Sunday brunches. We’d recommend: Goose & Gander, Brix, or Auberge du Soleil depending on which is closest to where you’re staying!
Champagne Tasting at Domaine Carneros
Late lunch in Sausalito if you didn’t get the chance to stop on your way into town
Sunday, Day 3 – Option B if you have an extra day to spend in Napa Valley!
With an extra day in Napa, you’ll have time to explore Calistoga, an area many people miss on their trips!
Brunch at Sam’s Social Club
Champagne Tasting at Schramsberg
Tasting at Castello di Amorosa
Late lunch from Oakville Grocery on your way out of Calistoga – Easy to go sandwiches, apps, etc.
Pool time at Silverado Resort (Napa has pleasant, sunny weather most of the year)
(Tasting at Stags’ Leap Winery if you’d rather do another tasting or are visiting in a cooler time of year!)
Dinner and drinks at Ad Hoc
Monday, Optional Day 4
Late breakfast at Grace’s Table
Drive back to San Francisco and fly home
If you have a late flight, this would be the perfect day for the spa!
Images: Michael Warwick / Shutterstock; Giphy (2)
It’s no secret that travel in the time of COVID-19 is a polarizing subject. While some of us can no longer resist the urge to escape and resume some semblance of normalcy, others are wary about resuming travel as usual. I’m still hesitant to get on an airplane, so for my recent Labor Day getaway, I focused on locations within driving distance of NYC. And I’m so glad I did, because it gave me the opportunity to explore a place I’d always meant to check out but often put off in favor of more exotic spots: Kennebunkport, Maine.
Kennebunkport is a shipbuilding and fishing village in southern Maine known for its beautiful beaches and delicious seafood, and is also the summer home of the Bush family (#TBT). Dock Square in the center of town is chock-full of adorable shops, fantastic restaurants, and incredible views of the Kennebunk River.
Maine is a great option for travel right now because it’s one of the states with the lowest number of COVID cases, and it takes safety precautions very seriously. All of the restaurants we visited spaced out the tables and took down names and phone numbers of diners for contact tracing purposes. Almost everyone walking around Dock Square wore masks (I even spotted a mailbox with individually packaged, free masks), and shops encouraged visitors to utilize their hand sanitizer while limiting the number of shoppers that could be inside at the same time. It’s also worth noting that, as of September 13, Maine requires out-of-state travelers to quarantine for 14 days or show proof of a negative COVID-19 PCR collected no more than 72 hours prior to arrival, excluding New Hampshire, Vermont, Connecticut, New Jersey, and New York.
How To Get There
Travelers from exempt states can easily get to Kennebunkport by car. The trip from NYC took just over five hours (with a short stop for food). We left on a Wednesday night and hit virtually no traffic. Coming back on Labor Day took us somewhere between five and a half to six hours. If you’re not within driving distance, other options include flying into Portland International Jetport, which is about 30 miles away, Manchester NH Airport, which is about 75 miles away, or Logan International Airport in Boston, which is about a 90-minute drive from Kennebunkport. Amtrak also offers a route to Wells, Maine, which is just ten minutes away from town.
Where To Stay
There’s no shortage of great options for accommodation in Kennebunkport at a variety of price points. Some hotels are right on the water near the center of town, while others are in slightly more residential areas that are just a short walk or drive from the action.
After some serious debate, we decided on Captain Lord Mansion, a charming bed and breakfast, which was at one time the home of sea merchant and shipbuilder Captain Nathaniel Lord. What really stood out about Captain Lord Mansion was the combination of its charming Federal-style architecture with all the modern amenities of a luxury hotel. It was great being just a five-minute walk from town—removed enough that it felt like our own home, but close enough to all the spots in town we wanted to check out. The hotel was also meticulous about safety. Instead of the traditional sit-down communal breakfast, each morning we were sent individualized and pre-packaged breakfasts that were home-cooked and delicious. I’m still thinking about the freshly baked muffin with melted chocolate inside that I ate the first morning.
If you’d like to be right in the middle of town, The Kennebunkport Inn is a popular choice with an unbeatable location in the heart of Dock Square. If you’re a beach bum, The Tides Beach Club is the only waterfront hotel on Goose Rocks Beach, which is one of the most gorgeous beaches in the area. Keep in mind, though, that you’ll be five to six miles from Dock Square, so unless you’re going for a Cast Away vibe, having a car will be key if you choose this hotel and want to explore the heart of Kennebunkport. Each hotel’s webpage details its safety precautions, so you can compare and decide where you feel the most comfortable.
How To Get Around
One of Kennebunkport’s selling points is its walkability. Almost all of the most popular spots are within walking distance of each other. That said, it was useful to have a car when exploring Goose Rocks Beach and some of the more remote restaurants. Though we didn’t have the need for an Uber or Lyft, they can be difficult to come by.
One popular alternative to a car is to rent a bike. It’s so popular, in fact, that when we tried renting bikes for fun for a half-day, Coastal Maine Kayak and Bike had none left! We did snag two of the few remaining bikes at Kennebunkport Bicycle Company, though, but if you’re committed to biking, it’s best to book early on during your trip or possibly make a reservation in advance.
Where To Eat
One of the main reasons I travel is for food, and my favorite part of planning any trip is mapping out each night’s dinner. Kennebunkport did not disappoint. Not only are the lobster and seafood options incredible and fresh, but you can also find places to eat that range from a casual shack to a multiple-course prix fixe dinner.
Our favorite spot was Mabel’s Lobster Claw. The ambiance was quaint and casual, with two large outdoor dining sections under tents. Mabel’s is a favorite of the Bush family and other famous names. I overheard a waitress telling another table that Martha Stewart and Patrick Dempsey were there earlier that week. After eating there myself, I can attest that the food is definitely worth the hype. The New England clam chowder was creamy and loaded with clams, and the lobster was perfection. For dessert, Mabel’s offers a blueberry pie featuring Maine wild blueberries, which are smaller and more flavorful than your typical blueberry. I’m not normally a huge fan of blueberries, but after this pie, I am a wild blueberry convert! FYI, they close for the winter starting September 27th, but they should open back up in April.
For a splurge meal, it’s worth checking out The White Barn Inn Restaurant. They offer a four-course prix fixe dinner that combines local ingredients with the inventiveness of a Michelin star restaurant. The service was impeccable and worthy of the hefty price tag, which is more than I can say for some of the other expensive restaurants in the area (ahem, Earth at Hidden Pond). This was one of our only indoor dining experiences, but my concerns were assuaged when I saw how far apart the tables were.
For lunch one day, we went to Arundel Wharf, which has a large outdoor seating section on the water. The seafood was fantastic, the vibe was casual, and the service was outstanding.
There’s an ongoing debate about where to get the best lobster roll in Kennebunkport. Perhaps the most widely touted spot is The Clam Shack, which is a literal shack in the center of town that has a long line of patrons at seemingly every hour. We enjoyed our rolls, but didn’t really understand the obsession. (I actually preferred the half-pint of fried shrimp we ordered as an appetizer.) A more underrated roll, absolutely loaded with generous chunks of lobster (an important consideration given the price), was the one at Arundel Wharf. But if you’re like me and prefer a hot, buttered Connecticut-style lobster roll to the traditional Maine style that’s cold and mixed with mayo, this won’t be your jam.
While some places are casual and seemed to have availability for walk-ins, it’s best to make dinner reservations in advance, especially if you’re looking to catch the sunset at waterfront spots like Alisson’s and Hurricane.
Last, but certainly not least, you must brave the line and grab ice cream at Rococo Ice Cream in town at least once. Rococo has a selection of 14 artisan flavors that rotate daily, unlike anything you’ve ever seen before. With flavors like Goat Cheese Blackberry Chambord to Sweet Avocado Cayenne, you’ll be pleasantly surprised at how good something so seemingly strange tastes in the form of ice cream. It’s also a woman-owned business, so we have no choice but to stan.
What To Do
Kennebunkport is a popular summer destination, especially for New Englanders, so the town was bustling with people when we stayed there. Whether you’re looking to simply lounge on a beach, or get more active, there’s plenty to do within and outside of town.
Maine has a number of beautiful beaches. If you’re looking for something close to town, Gooch’s Beach and Mother’s Beach are one and two miles respectively from Dock Square. Because of their proximity to town, they are popular and can get a bit crowded. For our beach day, we opted to drive the five miles to Goose Rocks Beach, which is a beautiful sandy beach that, though also popular, was a bit less congested than those close to town. We did do a quick trip to Mother’s Beach one night before dinner to catch the incredible sunset. Parking at the beaches can be a bit of a pain and you’ll need a pass from one of the nearby kiosks, so it’s best to get there either early or later in the day so you can find a spot without contemplating murder.
Maine also has a number of beautiful national parks, with one of the most famous being Acadia National Park. However, that’s another three to three and a half hours north of Kennebunkport. We didn’t want to make that kind of a drive, so we opted for a more local and off-the-beaten-path option for our dose of nature: a forest therapy guided walk. Forest therapy is inspired by the Japanese practice of “forest bathing”, or shinrin-yoku, and encourages participants to activate all of their senses and immerse themselves in the natural world. Some of the benefits of forest therapy include a boost to the immune system, lower blood pressure, and relaxation. It was just the escape we needed after living through six months of the dumpster fire that’s been 2020.
For casual drinks and a fun, lively outdoor patio, we spent a couple of hours one afternoon at Old Vines Wine Bar. The service was great and they had fun, live music.
In case my food obsession wasn’t already apparent, we spent one afternoon doing a foodie walking tour, which was a great way to get to know the town and familiarize ourselves with the local cuisine. We sampled clam chowder, the aforementioned Federal Jack’s lobster roll, tried local mead (also known as honey wine), had hand-roasted coffee and macaroons, and capped the day off with whoopie pies, the official state treat of Maine. How I’d gone 30-plus years without ever trying a whoopie pie is a shame that will stay with me for years to come.
Dock Square has a number of cute shops with local provisions. One of our favorites was Maine-ly Drizzle, which featured a number of unique infused olive oils and vinegars that you could sample (the stations were frequently cleaned and refreshed and only a few patrons were allowed in at a time).
☆ Check into hotel
☆ Explore the town, either on your own or with the foodie walking tour
☆ Catch the sunset at Mother’s Beach
☆ Dinner at Arundel’s Wharf
☆ Spend the day at Goose Rocks Beach
☆ Late afternoon ice cream at Rococo’s
☆ Dinner at Mabel’s Lobster Claw (car needed if you’re staying near Dock Square)
☆ Forest therapy guided walk (car needed if you’re staying near Dock Square)
☆ Rent bikes and ride alongside Gooch’s Beach
☆ Late afternoon drinks at Old Vines Wine Bar
☆ Dinner at White Barn Inn (car needed if you’re staying near Dock Square)
Images: Amanda Reiss
Hudson Valley is hot right now. The trendy upstate playground has been drawing city dwellers (along with the Vanderbilts and Rockefellers) for years, but given the current sitch, it’s even more popular these days. Good thing restaurants have reopened and local developers have been going after fixer-uppers with hotel potential, like Chip and Joanna Gaines with a vengeance.
Just as New Yorkers flock to the Hamptons in the summer, Manhattan creatives come to Hudson Valley to hibernate in the fall and winter. And considering most of the land surrounding this grouping of idyllic towns and hamlets is either covered by water or trees, it’s quite ideal for social distancing and keeping your six-feet-apart stance.
Whether you’re getting away for the weekend with your besties or bae, or planning a solo trip because that’s the kind of self-sufficient traveler you are, Hudson Valley has it all. And we’ve rounded up the best places to stay and things to do while you’re there. Read on for our top recs and Insta-worthy locales.
Where Is Hudson Valley?
Hudson Valley is in New York, duh. (Hudson River, anyone?) Hudson Valley is technically comprised of a bunch of different waterfront cities and towns, as well as rural farmlands and forests, so you can easily get your glamping on here or post up in an old Victorian-house-turned bougie hotel. HV stretches as far as the capital Albany in the north, toward Yonkers and Westchester County bordering NYC in the south. For trip planning purposes, some of the best spots to check out in Hudson Valley are Hudson, New Paltz, Beacon, Kingston, Woodstock, Rhinebeck, Gardiner, Tarrytown, and Sleepy Hollow. (Yes, Sleepy Hollow is a real place with charmingly spooky vibes. But that’s a given.)
How Far Is Hudson Valley From New York City?
Hudson Valley is much closer to New York City, than, say, the Hamptons, which is why New Yorkers are trading in The Big Apple for apple picking in the sticks. Depending on where you’re heading, you can be there in as little as 30 to 40 minutes, or a few hours. From NYC to Hudson, NY it’s roughly 107 miles.
How To Get To Hudson Valley
Road trip, obvi! The scenic route is much preferred, especially if you’re traveling from non-NYC places (and if you don’t want to sit near strangers for social distance reasons). With that said, Metro-North and Amtrak are options if you don’t have your own wheels or don’t want to drive. Just mask up at Grand Central Station or Penn Station, grab a seat six feet away, and chill for two hours until you get to Hudson, or wherever you’re going. Note: Metro-North service ends at Poughkeepsie, with Amtrak’s Empire Corridor trains continuing north to and beyond Albany.
How To Get Around Hudson Valley
If you’re a Hudson Valley newbie, you might assume everywhere within the area is relatively close. On the contrary, it’s much more spread out and Ubers and cabs are somewhat nonexistent—or super f*cking expensive. So, with that in mind, pick an area and stick to it instead of trying to do the most in a weekend. Or plan ahead and hire a driver, because drinking and driving isn’t cute. We’ve also curated these thoughtful itineraries below based on geographical whereabouts and you’re welcome for that.
Things To Do In Hudson, NY
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Historic Hudson is clearly the HBIC of Hudson Valley. Not only does Hudson proper bear the namesake of the upstate hotspot, but it has one of the longest main streets, packed to the gills with cute shops, hotels, and restaurants, plus antique stores and art galleries. As for activities, when you’re not playing House Hunters: Hudson Valley or bopping from one mid-century furniture store to the next, try one of these delights:
Stop by Opus 40 in Saugerties on the drive up to Hudson. You’ve probably seen snaps of the outdoor sculpture park on your ‘gram, and it’s high time you go.
Let your inner wino loose at happy hour at Sonder Hudson on Warren St.
Be one with nature (the Catskills is right next door and prime hiking territory).
Get blitzed on a craft brewery tour with stops at Hudson Valley Brewery, Hudson Brewing Company, Yard Owl Craft Brewery, Suarez Family Brewery, and Two Way Brewing Company (you can also ferry to breweries if you don’t want to drink and drive to farther ones #smart).
Antique your ass off. The downtown stores can be pricey, but drive to nearby Coxsackie Antique Center for the good finds and then you can lunch at Reds, a locals-loved fish fry joint.
Hit up The Quiet Botanist on Warren St. for dry botanicals and apothecary elixirs.
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Where To Stay In Hudson, NY
We live for The Maker, the newest boutique hotel that opened this past summer. With the trendiest digs in HV (think: a Georgian mansion filled with fringed lamps, jewel-tone interiors, lots of sumptuous velvet couches, and ‘20s vibes), rooms don’t come cheap. Peak season fall/winter rates range from $350-1,200 a night on weekends, but #YOLO. There’s an all-day Euro-inspired café, a restaurant housed in a glass conservatory, and a speakeasy-style lounge tucked away in a 19th century restored carriage house. Then there are the rooms. 11 swanky suites and rooms designed with a boho sensibility are themed after The Artist, The Architect, The Writer, The Gardener, and other creatives you can bump into around Hudson.
Outside The Maker, hang a right down Warren, then a left toward the train station and you’ll run into Wm. Farmer and Sons. This modern-meets-vintage hotel and bar room also has 11 dreamy rooms (most with clawfoot tubs you’ll never want to get out of) and thoughtful extras that really make a betch feel at home. I mean, look at these details?!
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The bright and cozy sitting area in our Anne Marie suite is perfect for kicking your feet up with a glass of wine or beer from the mini bar, challenging your travel companion in a game of gin rummy or just chilling out in front of the tube. Whatever your pleasure, relax, stay, enjoy the moment.
Their restaurant is tops for cozy, dimly-lit vibes and a damn good menu, with signatures ranging from SNAIL LASAGNA and roasted broccoli parm, to cast-iron caraflex cabbage with foie gras if you’re about that foraged life. And let’s not forget the gorg farm-to-glass cocktails.
For a more affordable alternative, check into The Wick, Hudson, a Tribute Portfolio Hotel. It’s nice, clean, pet-friendly, directly across from the train station, and right around the corner from Warren Street. Rates start at $180 a night.
Where To Eat In Hudson, NY
Aside from the aforementioned haunts, these restaurants and bars are also noteworthy in town: The Cascades for deli favorites, Swoon Kitchenbar for brasserie fare, Backbar for Malaysian cuisine, Grazin’ Diner for burgers, Hudson Food Studio for killer Vietnamese cuisine, Lil’ Deb’s Oasis and pop-up Feugo 69 for Pan-Latin nibbles and plenty of quirky flair, and the Tavern at Rivertown Lodge for brunch or dinner in a revamped 1920s movie theater. And bar-bookshop The Spotty Dog!
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Things To Do In New Paltz, NY
The adorable village of New Paltz sits in between the Gunks (Shawangunk Mountains) and Catskill Mountains, 90 miles north of NYC. New Paltz and Hudson couldn’t be more different however, and are about 40 minutes from one another. While Hudson is a postcard-perfect movie set stand-in, New Paltz is a more remote college town compared to “Upstate’s Downtown”.
There’s still a main drag dotted with the usual suspects—bars, restaurants, novelty stores, and artsy randoms—but this Ulster County enclave is also smack dab in the middle of protected nature preserves. As for other ways to pass your time, we’ve got you covered.
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🎃Happy Halloween! Don’t forget about our Outdoor Orchard Trick-or-Treat event today — we will have candy stations for kids, a spiked festive cocktail, and a $150 gift card raffle for anyone who is dressed in costume. We will be open until 7pm, hope to see you! . 📸: @diannnnneee . . . . . . #twinstarorchards #halloween #trickortreat #pumpkin #spooky #costume #fall #pumpkins #scary #boo #autumn #halloweenfun #halloweentime #photooftheday #cider #hardcider #drycider #hudsonvalley #cidertime #farmstand #tastethisnext #local #newyork #hudsonvalleyeats #upstateny #hudsonvalleyevents #getwithtipsy #hudsonvalleydogs #poughkeepsieny #upstate
New Paltz is a PSL-sipping, plaid-wearing, apple-picking basic bitch’s wet dream. And even though there are breweries and wineries galore, educate yourself and go to a phenom cidery, k? Brooklyn Cider House set up production here for good reason, and their growing grounds (Twin Star Orchards) should be your first stop when you’re ~thirsty~. Wood-fired pies, mouthwatering burgers, and hard ciders that will blow your mind await. P.S. backdrops include cute ponds and vines for one-foot-forward Insta opps.
Nestled in the heart of the Gunks is Mohonk Preserve, New York’s largest nonprofit nature preserve. Surrounding the historic Mohonk Mountain House, a Victorian “Castle of New Paltz” that dates back to 1869, you can explore the Preserve’s 8,000 acres of mountain cliffs, forests, fields, and streams from one of five local trailheads. According to mohonkpreserve.org, a day-use pass is $15 for hikers and $20 for bikers, climbers, and horseback riders (if you plan on getting your gallop on by bringing your own horse). There’s also cross-country skiing and snowshoeing in the winter.
Stroll the impressive lineup of 17th-century abodes, churches, and archaeological sites that line Historic Huguenot Street, where the area’s first French settlers moved in.
Head to Robibero Family Vineyards to sample the local grapes, or take a short drive over to Gardiner’s Whitecliff Vineyard and Winery for an outside tasting by reservation.
Stock up on artisan kitchenwares at Blue Cashew.
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Where To Stay In And Around New Paltz, NY
Bougies and people that like to stay put can live their best life at Mohonk Mountain House. Whether you’re traveling with your boo or your (small) crew, their grand estate rooms with terraces overlooking the peaks and valleys are unparalleled in the area. Plus there’s an epic spa and we could all use a little more self-care these days. Even though rates start in the $500-700+ range, you’ll be relieved to know it’s all-inclusive style with three daily meals and unlimited activities. And I’m not talking free cards in the lounge. Try your hand at tomahawk throwing, lace up some skates over at the Skating Pavilion, become a disc golf pro, go rock scrambling through the Labyrinth and Lemon Squeeze, and do all the sporty things during a round of croquet, bocce, or shuffleboard.
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Fall is better in the mountains 🍂🏰🍁 📷: @sonoyy . . . #mohonkmountainhouse #mohonk #happyplace #getoutside#greatoutdoors #fallfoliage #fallcolors #fall #biking #nightphotography #aerialphotography #naturephotography #getaway #weekendgetaway #boating #running #familyvacation #rockclimbing #mountaintop #mountainresort #resort #autumn #mountainbiking #archery #romanticgetaway #hudsonvalley #upstateny #upstatenewyork #historichotelsofamerica #historiclandmark
Hasbrouck House: I could wax poetic for days about how awesome this undiscovered gem in Stone Ridge is. For starters, it’s a restored 18th-century Dutch Colonial mansion that’s downright dreamy—and right outside New Paltz. 25 well-appointed rooms with modern bathrooms are spread out across the main building, Stable House, Carriage House, and three-bedroom private cottage. For $250+ a night, you can expect all the bells and whistles that come with proper Hudson Valley habitats, but you won’t blow your entire paycheck staying here. There’s free parking on the premises along with doughnuts and cider in the morning, as well as complimentary passes to Minnewaska State Park and Mohonk Preserve, and there’s also plenty of forest bathing opps around their 50 acres and private lake. When you get hungry, pop into the onsite bar and restaurant, Butterfield, or be on the lookout for the Baba Vegan Food Truck that swings by once a week to satisfy plant-based cravings. A basement billiards room, hot air balloon bedecked lounge with board games, and Aesop amenities round out their list of additional perks.
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Hang in there friends! We’ll be saving this seat just for you!💕 . . . . . 📷@lavina.s #hasbrouckhouse #hasbrouckhouseny #stoneridgenewyork #catskillshotel #catskillshotels #hudsonvalleyhotel #boutiquehotel #luxuryhotel #escapebrooklyn #escapebkln #andnorth #upstateandchill #romantichotel #hudsonvalley #upstatehotel #cntraveler
Where To Eat In New Paltz, Stone Ridge & Woodstock, NY
Spend the day at Arrowood Farm Brewery, where you can sip craft ales and cocktails by fire pits while munching on Bavarian pretzels and tostadas.
In downtown New Paltz, we like Main Street Bistro, Bacchus, Clemson Bros., A Tavola Trattoria, Main Course Marketplace, Huckleberry, and IPho for banging noodle soups, bánh mì, and vermicelli.
Go into a fried chicken coma at Kitchenette Chicken Shack in High Falls—and good luck not trying to go back 20 times during your trip.
For breakfast or lunch in Stone Ridge, hit The Roost or Hash.
For one of the best dinners of your life in Hudson Valley, make a res at Butterfield at Hasbrouck House, where everything is local AF from the farm-grown veggies and cultured butter, to the house-made bread, trout, duck, and venison dishes.
For other dinner options in Woodstock and Saugerties, there’s Phoenicia Diner’s sister spot Dixon’s Roadside BBQ, Silvia, and The Red Onion.
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This is what we call early sweater weather, when the days are full of sunshine and the evenings are getting cozy. ⠀ Come hang with us this weekend ☀️🍂 ⠀ WEEKEND HOURS Saturday 12-10 Sunday 11:30-8 ⠀ Cheers! ⠀ #hudsonvalleyhappenings #fall #catskills #accordny #hudsonvalley #upstateny #hygge #farmbrewery #drinklocal #eatlocal #beer #craftbeerlover
Things To Do In Tarrytown & Sleepy Hollow, NY
Stroll the Scenic Hudson RiverWalk Park at Tarrytown, which comprises 31+ miles along the shoreline from Tarrytown up.
Visit The Great Jack O’Lantern Blaze. From now through Nov 22nd, see 7,000 pumpkins light up fall nights in Croton-on-Hudson.
Get your spook on (and relive 4th grade English class) learning about the Legend of Sleepy Hollow and the Headless Horseman on a walking tour of the Sleepy Hollow Cemetery. P.S., Washington Irving is obviously buried here.
Tour the gardens at Lyndhurst. Hudson Valley has been home to some of the most powerful families of New York over the years, and Lyndhurst (AKA the Jay Gould Estate) is serious goals. As one of the most impressive Gothic Revival marvels like, ever, you have to see this thing in person—and obviously take photos. Even the Westminster Kennel Club Dog Show is moving to Lyndhurst in June 2021 because it’s that major. While inside tours are closed for the season, you can still purchase a Daily Grounds Pass to wander around and contemplate what life must be like for the 1%.
Also worth mentioning is another one of Tarrytown’s most famous homes: Kykuit, the Rockefeller Estate. It’s currently closed due to the pandemic, but boy, will it be a beauty to see when it reopens in the new year.
Where To Stay In Tarrytown, NY
If you’re looking for a low-key weekend or a workcation just minutes from Manhattan, check into Tarrytown House Estate, where complimentary WiFi and desks make WFH totally doable—especially when you can sneak drinks by the lawn fire pits in between Zooms. This Westchester County staple has been artfully restored and now boasts several modern rooms in the King Mansion, plus 26 acres of sprawling land fit for hiking, biking, and other outdoorsy things. They’re also pet-friendly and will arm your furry friend with a BarkBox upon arrival. Take a Sleepy Hollow kayak tour through the Hudson River, pick seasonal fruit at Wilkens Fruit & Fir Farm, do dinner at Goosefeather, and let your inner athlete loose during badminton, bocce, and croquet.
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Where To Eat In Tarrytown And Sleepy Hollow, NY
Make a res at Chef Dale Talde’s Goosefeather for crazy good Chinese barbecue and dim sum under strings of backyard lights. If you’re looking for vegan-friendly options, check out Sweet Grass Grill. Waterfront tavern RiverMarket is great for a biodynamic wine list and thoughtfully curated market. There’s also The Twisted Oak for Italian-American signatures, Pik Nik BBQ for smoked meats, Bistro 12 for Mediterranean fare, and Hudson Farmer & the Fish for sweeping views and seasonal staples.
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Anytime is a good time for pizza 🍕 Come and get one of our wood fire pizzas designed to your liking. With toppings ranging from baby arugula to even jumbo shrimp 🍤 and much more! * * * * * #pizza #woodfiredpizza #tarrytown #restaurant #yummy #delicious #swag #cool #pretty #foodporn #appealing #drinks #cocktails #togo #takeout #delivery #ubereatsdelivery #doordash #goodtimes #drinks #slurp #bar #liquor #thirsty #instagood #wow #drinkup #photooftheday #greattime #instadaily
More Places We Love In Hudson Valley
Cedar Lakes Estate in Port Jervis, NY: Escape to the heart of Hudson Valley where your personal pine cottage is waiting. Cedar Lakes is now booking three- and four-night stays through winter. All meals, a selection of beverages (boozy and non), and use of the property are included in the $125 per person, per night resort fee. You’ll also be treated to the following comped activities: Monday night football in their Treehouse (!), morning farmer’s markets stocked with fresh produce, Friday night trivia, and Saturday fall fests with campy pastimes (think canoeing, tennis, fishing, basketball, field games, and more). Did we mention there are Bob Ross-inspired paint nights? (BYO wig!)
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GOOD NEWS! We are now offering shorter stays beginning October 5 🍂 Come enjoy 3-night stays, either Monday-Thursday or Thursday-Sunday in our Sleepy Pine Cottages or Garden Suites beginning October 5.* (All other cottages continue to require a 6-night stay.) Interested in the Farmhouse? Enter FALLFARMHOUSE for 20% off from now until November 22 🎃 *All accommodations are Monday-Sunday for Thanksgiving week
Crabtree’s Kittle House Restaurant & Inn in Chappaqua, NY: Crabtree is another beyond-cute inn made for a romantic getaway with your main. Nestled in a hamlet in Westchester County, it has charm for days and maybe a few ghosts, since it was built in 1790 and served as a former roadhouse during the Prohibition era. Famous for hosting late-night ragers before becoming a private girls’ school and then a restaurant and inn, it has quite the collection of stories within its walls (along with an award-winning wine cellar in the basement). The restaurant’s ever-changing, locally-sourced menu also makes this landmark a one-stop shop for old-world accommodations and fine dining.
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Treat Dad to a special Father’s Day this Sunday! Choose from our brunch and dinner options on premise and takeout ➡️ www.crabtreeskittlehouse.com/dining #fathersday #dad #garden #outside #socialdistancing #brunch #dinner #takeout #togo #curbside #family #together #special #hudsonvalley #westchester
Image: Mohonk Rd, New Paltz. Jueun Song / Unsplash
If you happened to tie the knot before or during the pandemic and have put the honeymoon on pause until flying feels safe again, sneaking in an end-of-summer or early fall escape is still plausible—and probably much-needed.
Enter the Hamptons: an easily-accessible destination if you happen to reside in the tri-state area—or even parts of New England—and don’t mind a drive or a scenic ferry route.
With an expansive backyard that checks all the vacation-worthy boxes (sun, surf, and sand), heading out east is always a good idea in our book. Responsible, socially distant practices and policies also make the Hamptons feel not only doable these days, but welcoming.
Below are our picks for where to stay, dine, and explore after your weekender bag is packed and you’re ready to go.
Where To Stay
Amangansett’s newest residence, The Roundtree, is beyond dreamy, and ideal for getting away in style. The 15-room, pet-friendly boutique hotel just opened last month, so you know it’s clean, disinfected on the regular, and COVID-compliant. There are even cell phone sanitizing stations in your personal quarters. Now, how’s that for safety precautions?
You can choose between deluxe rooms, suites, and cottages in centuries-old refurbished digs that all come with Frette linens, Matouk towels, and Grown Alchemist bath products. The Roundtree is basically our #1 pick for romance, intimacy, and luxury, all wrapped up in one. And when you book four or more nights, they’ll set you up with a chef for a fall harvest dinner experience for two on the property.
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“A stay at The Roundtree means you’ll get to know your neighbors, since there’s so few of you. Perhaps you’re just drinking rose, or, since The Roundtree allows pets, your dog will inevitably run up to greet another on its rolling green grounds. Then you’ll start chatting (six feet apart, of course), and soon enough, you’re waving to them at breakfast or giving them a nod as you both dive into yet another Zoom call. Everything is so laid back, so friendly, that it adds to the atmosphere.” – @ejtay @voguemagazine Consider one of our stand-alone cottages or rooms for weekly and monthly rentals this fall for a socially distanced #workfromvacation experience #theroundtreeamagansett #theroundtreehotel #theroundtree
Smack dab in the middle of Montauk is the notoriously laid-back “End of the World” Surf Lodge. Kitschy balcony hammocks and a fleet of loaner bikes are part of the perks when it comes to staying here, as is close proximity to the beach—making it a coveted hangout for eating, sleeping, surfing, and repeating. Standard rooms (plus junior and master suites) are boho, yet minimalistic. Their famous outdoor concert series is on pause given the pandemic, but the restaurant remains open with six-feet-apart al fresco seating.
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aaaand we’re back! Starting today we’re officially open to hotel guests (only!)—with a new set of safety protocols in place. In the face of all this uncertainty we hope to bring you some sense of comfort and familiarity, and create the escape we all need right now. Rooms are still available for the July 4th weekend and we have take-away dining starting Friday for our neighbors, so let’s finally get this summer started! … Protocols include: -Employees wear masks at all times -Employees are tested weekly -Contactless sanitizing stations -Both in-house cleaning and professional commercial cleaning -Encouraging staff to social-distance outside of work -Immediate response and transparency to a positive test
One of the sweetest stays in the Hamptons can be found at Baron’s Cove in the quaint whaling village of Sag Harbor. Ideal for a lover’s retreat, the year-round sophisticated refuge boasts 67 rooms, many with gated terraces tailored to sitting outside for sunset cocktails. Its upstairs restaurant is perfect for breakfast, lunch, or dinner. The spacious pool and surrounding gardens serve as the perfect adult playground, so it’s no wonder Billy Joel, Truman Capote, and Jackson Pollock have all checked in over the years. Pro tip: book in the fall and winter to save on rates.
Where To Eat
If you happen to be near Bridgehampton, our go-to romantic dinner for two is always at the Topping Rose House. The uber-chic Jean-Georges restaurant is a must for celebs, socialites, and diners who want a meal in a swanky setting. It’s also one of the few premiere spots that’s open year-round for breakfast, lunch, dinner, and cocktails. As far as the menu goes, the black truffle and Fontina cheese pizza is a must, as are the roasted Maine lobster, seared black sea bass, and crispy salmon sushi.
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Down the road in Bridgehampton is the quaint Bridgehampton Inn & Restaurant, with an idyllic backyard and locally sourced menu that changes from season to season. On Fridays, there’s live music, and Kyle, their esteemed wizard behind the bar, will be more than eager to whip up a bespoke aperitif of your choosing. The family-run establishment also owns the Loaves & Fishes Food Store next door, so be sure to stop in for newlywed must-haves for the home—or to update your registry.
More staples in Montauk include roadside seafood shack The Clam Bar for lobster rolls and fried whole belly clams, plus a smorgasbord of other seafood favorites under a cascade of yellow umbrellas. It’s only open for lunch, and highly addictive after you go the first time.
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Navy Beach is another spot for good vibes and good times, with picnic tables nestled in the sand and a stay-all-day mentality that makes it hard to leave—and harder to not order more wine. (They have one of the largest selections of rosé in the Hamptons.) Food highlights include the buttermilk fried chicken, jumbo lump crab cake and, obviously, the navy burger. Their sunset views are legendary, and their 200-foot private beach is prime real estate for honeymoon happenings (aka Instagrams).
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Get a taste of Manhattan in Montauk at Scarpetta at Gurney’s Montauk Hotel & Spa, which is not only on the beach, but set under a cascade of twinkling lights for the ultimate ambiance. You’ll undoubtedly order the classic Italian pastas for the table, but don’t overlook the fresh crudi, the black cod, or the Wagyu strip. Then there’s Showfish at Gurney’s Star Island, with an ingredient-driven menu of veggie-forward dishes as well as crazy good land and sea options.
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Scarpetta Newport will be reopening tonight and tomorrow from 5:30pm – 10:00pm for both outdoor and limited indoor seating, ordering for takeout and in-room dining for guests of the resort. This service will resume again on Thursday, June 11th – Sunday, June 14th. Scarpetta @gurneysnewport will continue to evaluate the situation and focus on long-term planning for its reopening. Wishing our Newport employees, guests and community a safe and strong reopening 🤎
Duryea’s may sound like a laid-back lobster deck with a view, but it’s more like St. Barths or St. Tropez when you arrive to the chic AF destination. Here, the rosé is always flowing, and the plateau de fruits de mer are on point. They’re renowned for their lobster Cobb salad and crudité platters, but it’s the cushy banquettes, overhead fishnet canopy, and effortlessly cool attitude that makes us fall in love with this Montauk mainstay again and again.
If you’ve never been to Tutto il Giorno, make a reservation now. So f*cking pretty, it’s exactly where you want to toast to your nuptials over shared plates of Mediterranean fare. Designed (and owned) by Donna Karan and her daughter, Gabby Karan De Felice, it’s the epitome of backyard garden goals. And they have outposts in both Sag Harbor and Southampton, so you’ll have ample opportunities to visit, depending on where you’re staying.
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Main Street Tavern is a new spot that just opened this summer, from the team behind Highway Restaurant & Bar in East Hampton. Already gaining a considerable amount of buzz, MST is the tasty newbie on the block with delicious food and charm to boot. They’re currently only offering dinner through takeout or in their outdoor socially distanced beer garden, but definitely order the crispy shrimp, fish and chips, and baked clams.
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Other strong contenders for breakfast, lunch, and dinner include: Cowfish (Hampton Bays), Nick & Toni’s (East Hampton), Coche Comedor (by the team behind Nick & Toni’s, La Fondita, and Towline BBQ), The Backyard at Sole East (Montauk), Wölffer Kitchen (Amagansett), Le Bilboquet (Sag Harbor), Greek gem Elaia Estiatorio (Bridgehampton), and il Buco at Mostrador Marram.
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What To Do (Socially Distanced)
Yes, the beaches are open—as are almost all restaurants and shops in the various towns—but, obviously, wear your mask and lay your towel, chair, etc. away from others to do your part. For more information on beach permits and parking, check out this handy guide.
Spinning to the beat may be paused at most indoor studios around the world still, but, naturally, the Hamptons takes it outdoors. Grab a bike for SoulOutside at any of the the Southampton, Bridgehampton, Water Mill, and Montauk locations, but be sure to book early.
Wölffer Estate Drive-Thru
Chances are you’ve seen the socially distant drive-through rosé cart on the ‘gram, because it’s pretty much the cutest thing ever. Pull up, select your pink or bubbly of choice (along with whites, reds, and ciders), then be on your way, contact-free. Should you desire more of a vineyard-type experience, the Estate and Wine Stand are currently offering tasting reservations (with food) six feet apart.
The drive-thru can be found at the Wölffer Estate Wine Stand in Sagaponack, New York. It’s open daily from 11am to 7pm.
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Happy Friday! Need a restock on your favorite Wölffer products for your virtual happy hour? Our drive-thru is open 11am-6pm daily 💕 . . . . . . #wolfferestatevineyard #wolffer #wolfferestatewine #wine #spirits #cider #eastend #hamptons #amagansett #sagharbor #montauk #nyc #localeats #localbusiness #familybusiness #sustainable #sustainablefarming #sustainability #estatewines #localwines #roselocal #rosé #drivethru
Bike Around Town
Most hotels provide complimentary wheels to scoot around the Hamptons in the summer, and you can be as spread out as you want when riding. Should you be in a house or Airbnb, here are a few more places to rent from:
- Khanh Sports
- Amagansett Beach & Bicycle
- Dan’s Bike Rental
- Sag Harbor Cycle Company
- Rotations Bicycle Center
Plan A Clambake On The Beach
Hampton Clambake will bring the beach party to you, with a fully organized and delicious clambake on the South and North forks.
Take Advantage of NYC-Turned-Hamptons Pop-Up Restaurants
This summer, New York City notables such as Marea, Carbone, Kissaki and the aforementioned il Buco have traveled out East to bring the people what they want: platters of spicy rigatoni to go. Some of these pop-ups come with a hefty price tag (like Marea’s dinner for four for $450), but you get to enjoy a Michelin-starred meal in the comfort of your own home. Plus, it’s a serious spread. Think: marinated olives, lobster and burrata, panzanella salad, steak with salsa verde, summer squash, sautéed greens, seasonal pie, and a bottle of Hampton Water Rosé.
Image: Hamish Duncan / Unsplash; theroundtreeamagansett, thesurflodge, baronscove, toppingrosehouse, bridgehamptoninnandrestaurant, theclambar, navybeachmontauk, scarpettarestaurants, duryeaslobsterdeck, tuttoilgiorno, themainstreettavern, monstradormarram, wolfferwine, mareanyc / Instagram
We may be living through a pandemic, but we’re still feeling the urge to travel (safely). After canceling trips that had been planned pre-pandemic, booking new trips we assured ourselves would be “totally fine” by the time they came around, and then having to cancel those, too, we’ve all come to accept that the pandemic has changed the travel game in 2020. Luckily, there are plenty of local places to safely explore that will give you just as much fun and relaxation as traveling abroad to somewhere dreamy, like St. Tropez. Okay, I’m exaggerating a bit—but to be honest, I did get a genuine feeling of being a world away when I traveled to Provincetown, a seaside town on Cape Cod.
There’s always something happening in Provincetown (which often goes by the nickname “P-Town”), even during a COVID-19 summer. If you Google “Provincetown”, you’ll instantly find all the historic info about it, like how it’s home to where the Mayflower landed in 1620. But what really makes this coastal town feel different from the rest is its free spirit and high energy. It’s a top LGBTQ+ destination, a haven for artists of all kinds, and it’s f*cking fun. Storefronts down the main street are decorated with signs that solidify the town’s strong message of love and acceptance. Commercial Street is a vibrant and easily walkable strip that serves as the town’s main street where you’ll find tons of stores, restaurants, and hotels.
One of the greatest benefits of traveling to P-Town during the pandemic is its mandatory safety measures. Social distancing is practiced at every establishment, with tables six feet apart at all restaurants and stores only permitting specified capacities. And mask enforcement is no joke here. You can’t walk around Commercial Street without a mask on. There are signs deeming it a “mandatory mask zone”.
It might sound like walking around a summer town with a mask on is a drag, but TBH, it really made me feel safe and put my mind at ease. And FYI, as of August 4, 2020, Massachusetts requires out-of-state travelers to quarantine for 14 days or show proof of a recent negative COVID-19 test, excluding New York, New Jersey, Connecticut, Maine, New Hampshire, Vermont, and Hawaii.
How To Get There
Except for Hawaii, all exempt states whose travelers can visit Provincetown without quarantining are a manageable distance away by car. We drove from New York and clocked in a five-and-a-half-hour road trip there, but it was an enjoyable drive with almost no traffic. If you want to ball out, you can also get there by boat. If you don’t have a casual private yacht at your disposal, you can hop on a Boston Harbor Cruise (which leaves out of Boston, duh). The ride is 90 minutes each way, and round-trip tickets cost $94.
Pro tip: If you’re driving to P-Town, you *must* make a pit stop in Northwest Harwich to grab ice cream at a glorious place called Sweet Izzy. It’s pretty much on your way there and only 50 minutes outside of P-Town. It’s a full vegan ice cream shop, and all of its products are made in-house with only organic ingredients. We loved it so much we stopped once on the way there, and once on the way home (calories don’t count on vacation, right?). It’s also located directly next to a trampoline park, a local staple that’s been around for over 60 years. Definitely pay them a visit too (tickets cost $8 for 10 minutes), but remember to jump first and enjoy your ice cream second.
Where To Stay
Provincetown is a compact, small town, so here’s an easy rule of thumb for finding a hotel: if you want to stay on the main strip of town (which could be loud), look for hotels on or right off of Commercial Street. This street is adjacent to the water, so many establishments have water views or are waterfront hotels. If you want to be somewhere with a little less noise, but a short walking distance away from town, look for hotels on Bradford Street.
We opted for Eben House, a bed-and-breakfast on Bradford Street, so we were close to the action but also got a quiet night’s sleep. The grounds have great communal spaces, like a porch with an Insta-worthy hammock and a nautical-themed saltwater pool area. It’s also a 60-second walk to town, making it super convenient.
Other options are Pilgrim House, a “centrally-located, year-round” luxury hotel that is also home to The Landing Bistro and Bar; there’s also Salt House Inn, a fully renovated bed-and-breakfast located right in the center of town known for its signature house-made rustic breakfast.
Pro tip: Upon booking your reservations, ask your hotel what safety measures are in place. It’s nice to get away, but what good is a vacation without peace of mind?
How To Get Around
One of the many things that make P-town so great is that everything is pretty much walkable. The furthest distance we ever walked during our stay was 12 minutes, and it was a fun stroll through town. Having said that, if you need a taxi or Uber for any reason, they’re available.
Where To Eat
No matter where you choose to eat, you’re pretty much guaranteed to have a fun and safe experience in Provincetown. Restaurants and cafes cater to all cuisines, but given that it’s a coastal town, you can’t miss out on the fresh seafood.
Our favorite restaurant was Strangers and Saints, an innovative eatery in the art gallery area of town. The cocktails are top-notch, and each dish was better than the next. There are even three different outdoor areas to choose from upon making a reservation. We picked the front patio (which we loved), but the herb garden and back patio looked equally impressive.
You won’t be able to miss The Patio when walking through town. The outdoor deck is decorated with huge blue-striped umbrellas and string lights. The vibes are better than the food here, but it’s worth a visit, although it’s on the expensive side. Reservations are required with a credit card, and there’s a table limit of one hour and 45 minutes.
The historic Red Inn restaurant is “all about old-world charm and new-world pleasure”. It’s the town’s classiest place to eat and has a raw bar and cocktail happy hour from 2:30pm to 5:00pm daily.
For true P-town beach vibes, you need to hit up Canteen for drinks and lobster rolls. This beach shack is filled with tables painted with seafood puns like “Oh My Cod” and serves excellent pre-mixed cocktails and quick bites. There’s also access to the beach, making for a great photo backdrop after a few cocktails.
Pro tip: Since social distancing is practiced everywhere, reservations are a necessity during dinner hours. Aim to make your dinner reservations as late as possible, since most things shut down by 11 pm. Because you can’t go out to bars during this time, a late reservation will allow you to enjoy your day to the fullest and give you a table to enjoy cocktails later in the evening over dinner. Be sure to call ahead and ask if there’s a time limit for your table reservation.
What To Do
It was crowded during our weekday stay in town, but given it was the week of Carnival (P-town’s biggest celebration of the year), we heard it was actually pretty empty compared to a normal year. Since the parade was canceled, this was to be expected, but there were still people out and about. No matter when you choose to visit, manage your expectations knowing that you won’t get a 100% genuine experience in any town you travel to during COVID (for obvious reasons). I personally thought we wouldn’t be allowed out of our houses until 2021, so I’m just grateful to be able to travel at all, even locally.
Enjoy a day poolside and let your rainbow flag fly at the Boatslip waterfront resort. Their bread and butter is their famous “tea dance” happy hour, but it’s unfortunately canceled for the 2020 season due to COVID safety restrictions. There’s a $12 cover charge that gets you a lounge chair and towel (cash only), and be sure to get there early as it’s first come, first served. They’re famous for their Planter’s Punch cocktails, and after getting lit from just two of them, I can certainly see why.
There’s an abundance of ice cream shops and candy stores in town. ScottCakes, Provincetown Fudge Factory, Cabot’s Candy Factory, and Ptown Scoop are some of the best spots to indulge.
Rent bikes from Provincetown Bike Rentals and put in that cardio work on one of the many bike trails throughout the area. Given that it’s a coastal town at the cape’s tip, the beach options are endless. Pack a beach bag, and don’t forget the SPF.
Weed is legal in the glorious state of Massachusetts. All you need to score some goodies is a valid ID showing you’re over 18 years old. The lines can seem long at the town’s only dispensary, Curaleaf, but they move pretty fast. Also, make sure you have cash or a debit card on you, because they don’t accept credit cards.
☆ Make an ice cream pitstop at Sweet Izzy
☆ Check into hotel
☆ Explore Provincetown
☆ Pre-dinner drinks at The Canteen (Note: they do not take reservations, but you should be fine without them)
☆ Sunset dinner at The Patio (the reservation table limit is 1 hour 45 minutes and a credit card is required for reservations)
☆ Spend the day lounging poolside at The Boatslip
☆ $12 cover charge with lounge chair and towel (cash only)
☆ Come early (first come, first served. No reservations)
☆ Open 10am-4pm
☆ Pre-dinner drinks at Aquabar
☆ 9pm dinner reservation at Strangers & Saints
☆ Check out of hotel
☆ Grab coffee and treats to-go at the famous Provincetown Portuguese Bakery
☆ GTFO of P-Town and head home
Images: Joana Mascioli; James Kirkikis / Shutterstock.com
As you might recall from your EDM worshipping college days (an unfortunate but valid throwback), Ibiza is the dance music capital of the world. A place that proudly bears a title like that makes it easy to assume that it’s an island full of neon-wearing, Tiësto-loving douchebags dancing to music 24 hours a day. But you’d be wrong; there’s way more to love there. Yes, Ibiza is known for its wild party scene and high social status which, of course, comes with an expensive price tag. It’s a Balearic Island off of Spain’s mainland, so it’s a hassle to get to and plane tickets don’t come cheap, especially since most places don’t offer direct flights there. Lodging is also astronomically costly and a bottle of water at some of Ibiza’s most elite day and night clubs costs $20 (no exaggeration and they’re small-ass bottles, FML). While the raging party scene might be the first thing that comes to mind from what you see on the ‘gram, the island’s real beauty lies in its sights and beaches.
First of all, Spain in and of itself is a place you need to visit in your lifetime. The food is unreal, the people are a vibe, and there are a crazy amount of cities to explore. Ibiza might seem like a skippable stop, but I highly recommend making it part of your trip, especially while you’re young (YOLO). The island truly is one-of-a-kind, and the vibes here are really unlike anywhere else. As much as I had planned for this stop on my trip to be just a place to let loose and enjoy the “scene”, I was surprised to learn how much musical history exists here, dating back to the mid 20th century. I also had no idea how family-friendly (granted, bougie AF families) the island was. It’s unfortunately a pricey travel destination no matter how you slice it, but IMO it’s well worth the splurge. It is super over-the-top, but it’s totally on-brand and everything you’d expect from “the mecca of dance music.”
So, all things considered, is the Ibiza hype real? Does the gorgeous scenery find some weird harmony with the raging parties and dance music scene? The answer is…
Yes. If You’re A Partier, Ibiza Is DEF Worth Visiting.
I might be past my prime party girl years, but TBH, I still enjoy a night out dancing to hype music from time to time. Even if that weren’t the case, the music in Ibiza is really f*cking incredible. Whether you’re eating at a chill spot on the water, or it’s 4am in a bass-blaring nightclub, the music you hear in Ibiza is next level. There’s a reason Ibiza is known as the capital of this genre, and why almost every top DJ currently has or once had a lengthy summer residency there. You can arrive absolutely hating it, but after hearing the wide variety of electronic music Ibiza offers, you’ll leave this Spanish island a (low-key) EDM fan.
Music is only half of it, though. The places you go to dance to these beats are truly where the party lies. There is nothing like an Ibiza party. I repeat: NOTHING like it. It’s often imitated but never duplicated. Below you’ll find a selection of the craziest day club options, and later on, I’ll list some chiller ones, if you’re trying to spend your days resting up pre- or post- a wild night out. Making reservations for daybeds at these spots is always a fun (and expensive) option, but not necessary by any means.
Day Clubs (For Raging)
Ushuaïa: A newer hotel that quickly became an Ibiza staple. Catch their signature ANTS party here every Saturday for a poolside day party that continues on well into the night.
Ibiza Rocks Pool Party: Known as the “home of the pool party” in Ibiza, this newly rebranded day club is always a wild time. Get a VIP table if you really want to party like a
O Beach: Dance away in their pool as acrobats dance above you. It’s extra, but pretty much everything about Ibiza is extra, so why not.
In all honesty, if you’re coming to Ibiza to party, it’s very likely that you won’t even make it to any of those dayclubs…. because you’ll be sleeping until 3pm. Don’t worry though, you’ll find much of this island will be on the same time as you. The real parties at the nightclubs don’t start up until 1 or 2am here (for real), so your sleep schedule will be totally out of whack. I def recommend making #TeamNoSleep moves and going to at least one day party while you’re there, though. As far as nightclubs go, there are a few that are classic Ibiza staples and others that are ritzy and new. Blending a nice mix of the two will give you the most authentic sense of the new and old club culture here (which is a huge element of the island, as ridiculous as it sounds).
Pro tip: take a look at the DJ schedules online to see if anyone you’re remotely into is playing. Getting tickets in advance is also def the move (and will motivate you not to bail when you get too tired to do your makeup after you shower).
DC10: This place is pretty no-frills by Ibiza standards, but it’s an OG Ibiza classic. If you’re trying to go here, def catch one of their signature CircoLoco parties.
Hï Ibiza: Hï is by far the most extra nightclub in Ibiza, and because of that, it is the most expensive one as well. But, I assure you, it is a must-visit. This superclub is designed with totally over-the-top decor, like an outdoor playground slide and a huge neon crystal draped tree. Oh, and the bathroom has its own DJ… and party. It’s the craziest f*cking bathroom you’ll ever pee in.
Amnesia: Another “classic” nightclub that’s been open since the 70s. Before there was a law that mandated all clubs close at 3am in this part of the island, you’d be able to catch the sunrise through the greenhouse-style ceiling as you dance away. RIP! Now you can just dance until 3am and go to sleep “early” like a normal human being.
Pacha: A landmark of sorts for clubbing culture in Ibiza. It’s a bit dated, yet still classic. Pacha’s double cherry logo has become an island-wide symbol for nightlife.
As I said earlier, the people are super nice everywhere (oddly enough, especially the club staff and bouncers). But you should still use your street smarts and know your crowd since pickpocketing is very common in most of Spain. The parties are some of the best you’ll ever go to, but, like anywhere else, you should know to be careful of sketchy people and never leave your belongings unattended.
Like everything else on the scene in Ibiza, even the restaurants know how to turn up. The restaurants listed below serve bomb Spanish food and party vibes galore. Since Ibiza’s prime season (and the only season I recommend visiting in) is the summer, the island gets hella crowded. It’s always a “fun crowded”, but it definitely affects a hot spot’s availability. Point being: you NEED to make reservations at these places. If you’re not a planner and miss out on these spots, don’t say I didn’t warn you.
Cafe Mambo: This is my favorite restaurant on the planet. It’s located right on the beach and a big name DJ spins live music in a small booth near the dinner tables. The sunsets on this part of the island are so legendary that it’s a tradition for everyone to chant and clap once the sun finally goes down. I deadass got a tear in my eye as I experienced it because it was THAT beautiful and truly a magical moment. Ugh. K moving on… you will 100% need a res here, especially if you want a good table.
Destino: It’s hard for me to talk up these other two options after I just told you I cried watching the sunset at Mambo, but Destino is also an awesome time. It’s a huge venue you can’t miss that offers seven different menus to choose from for their lit dinner parties.
HEART: Dinner parties here have Cirque du Soleil-like performances and innovative eats. It’s also located in the marina, which is a cool area to go check out (aka stare in awe at million-dollar yachts while simultaneously fantasizing about winning the lottery.)
If You’re Over The Party Scene, Ibiza Is Still Absolutely Worth Visiting.
There’s a ton of culture, history, and scenic beauty that make Ibiza extremely vacation-worthy, even if you’re not a huge partier. You def won’t be forced to party your ass off if that’s not your thing, because there is plenty else to enjoy here. And let’s be real, with beaches this gorgeous, how can you be opposed?
Day Trip to Formentera
Formentera is a famous island off the coast of Ibiza. It’s about a 30-minute ferry ride away (they run pretty much every half hour, but keep your eye on the schedule for your return trip.) Spend your day hanging on the beach or riding scooters to explore the island’s distant bars and beaches. A lot of restaurants are located right on the beach and serve amazing authentic Spanish food. Throughout my entire two-week trip to Spain visiting four different cities, the best paella I had was at a restaurant called Beso Beach in Formentera. Def go there, but like everything else during a busy Ibiza summer, you’ll need to make a reservation in advance.
Explore Old Ibiza Town
A friend had told me I’d absolutely love the area of the island called “Old Ibiza Town”, so we decided to get our AirBnB there. While it was no shock that I wound up loving it, it did surprise me to learn how much music history it had. Throughout the 70s and 80s, big-time musicians like George Harrison vacationed here to visit Ibiza’s discothèque scene and celebrate music. You’ll notice the hippie history of the island is celebrated in a lot of places you’ll visit, but especially so in Old Town. The shopping here is absolutely incredible, with everything from chic boutiques to streetside booths. It’s a very family-friendly area of the island that also has a lot of small bars and local restaurants.
The Castle of Ibiza is located right in the heart of Old Town and is a solid hike, if that’s your thing. And while you’re up there, stroll the 2,000-year-old streets of Dalt Villa. And again, the sunsets are famous here for a reason (just make sure you’re on the right side of the island for it or else you’ll miss it)! San Antonio Bay is my personal favorite spot to catch a sunset. Make sure you also hit up the Marina Botafoch in Ibiza Town for a cocktail on the water.
Day Clubs (For Chillin’)
Nassau Beach Club: A clean, inviting beachside dayclub. Multitask sleeping off your hangover and getting a tan underneath the Spanish sun. Reservations recommended.
Blue Marlin: Blue Marlin has amazing food and drinks and daybeds that overlook the beach. The vibe goes from chill to lit around 5pm, so stay late if all that relaxing in the sun gets your energy in the mood to party.
Nikki Beach: You can never go wrong at the world famous Nikki Beach. I mean, who could hate a day club with a pool on a beach?
Sa Capella: It’s a former church, so eating within Sa Capella’s dining room’s stone walls will have you feeling fancy af. I guarantee you’ll love pretty much everything they’re serving too (if only the holy vibes could make the calories you consume not count).
Calma Bistró: A scenic restaurant serving some of Spain’s favorites right on the marina.
Fish Shack: Ok, so this is not glamorous in any way because it is quite literally a waterfront shack… that only serves fish. But it is the absolute best fish you’ll EVER have. Everything served that day is freshly caught in the morning and written on a plain chalkboard menu. Not only is the food to die for, but DJs frequent this place like crazy, so expect to catch some star power here.
All in all, Ibiza is a gorgeous island with a party scene pulse that can’t be topped. Whether you decide to keep your itinerary chill or lit, the people of Ibiza will always make a vacation here special. There are welcoming, interesting people everywhere you go, so let loose with the people around you and celebrate the good life together (or act like you got it like that.) The Ibiza hype is real indeed, and as you can def tell by now, I’m a big fan of it. Sure, your bank account (and your dignity) might be hurting after you get home, but do like the Spanish do. YOLO.
- Shop and stroll through the shops in Ibiza town if you want a more chill day, or get the party started early at Ushuaïa
- Dinner at Fish Shack (it’s cash only!)
- Walk off dinner with a 15 minute stroll along the bay to catch the sunset at Nobu Hotel
- Head out for the night and into the early hours of the morning at DC10
- Ferry to Formentera for the day—the ferry is 30 mins & runs pretty much every half hour
- Hang on the beach all day, or rent scooters at some point to explore the island’s beaches
- Enjoy a late lunch at Beso Beach (be sure to make a reservation here)
- Catch the sunset at Playa de Ses Illetes (the world’s best beach—30 min walk from Beso)
- Take ferry back to Ibiza (keep your eye on the ferry schedule times!) and get ready to go out at HI
- Try out a beach club during the day at Experimental Beach or have lunch in Old Ibiza Town, followed by hiking Castle de Ibiza
- Head to Cafe Mambo for music and dinner (reservations are a must to score a table)
- Go out at Amnesia
- Lunch and day drink the day away at Blue Marlin (reservations highly recommended) or if you want a break from partying, have a scenic lunch on the water at Calma Bistró and explore the rest of Puerto de Ibiza
- Nap on the beach and get your tan on
- One last night out at Ushuaïa
Images: Pawel Kazmierczak/Shutterstock
Unless you live under a rock that gets no cell reception, you know Tokyo is like, the hottest travel destination right now. It seems like every post with a Tokyo geotag is bursting with over-the-top colors that make you just want to dive in. I know that for most people, Tokyo is far af to get to. It’s also commonly considered an expensive and time-consuming commitment, but what trip isn’t, right? It’s hard for me to put into words how culturally enriching visiting Tokyo was. It was an adventurous, wild, delicious ride that I can’t recommend enough, but I’ll do my best…
My husband and I decided to take a much-anticipated (and super millennial) one-year anniversary trip across the world and decided to start our travels in none other than Tokyo, Japan. I only had three glorious days in Tokyo, so I jam-packed them and I was able to see so much of what this vibrant city has to offer. You can absolutely cram in the recommendations below, or spread them out over a solid week. The bottom line is that there’s never too much time in Tokyo.
A quick lesson on when it’s worth balling out on a swanky hotel: First, take into consideration how many nights you’ll be staying in that city and how expensive it generally is. If it’s a big city with lots to see and do, also consider how much time you’ll realistically be in that hotel room. If you have limited travel time and anticipate spending your days galavanting around nonstop, your hotel’s purpose will strictly be for getting ready and sleeping. It’s obvious when you break it down in simple terms, but most people don’t realize just how wasteful splurging on a hotel room can be. All the money you can save by booking a perfectly suitable budget hotel can go towards bougie dinners on your trip (or a shopping spree at YSL, your choice girl). Either way, be sure to consider all the factors before choosing a hotel.
Hotel Wing International Premium Tokyo Yotsuya: My husband and I stayed here and were probably here for a total of maybe 8 hours a day (including sleeping #TeamNoSleep). It was super affordable, clean, came with a queen-size bed and was only two blocks from a central Metro station.
Four Seasons Hotel Tokyo At Marunouchi: If it’s a Four Seasons, you know it’s lit. This hotel is as baller as they come and is located right across from a Metro station hub. What could po$$ibly hold you back from booking thi$?
Be warned that a common culture shock factor you’ll experience in Japan is a minimalistic mentality, especially with space. A majority of the hotel rooms in Tokyo are extremely small in comparison to the standards you’re used to, and commonly come furnished with just a twin bed. Make sure you take note of the bed size when booking your hotel and take note of how far it is to the nearest Metro station.
PSA: Your disgust for your local city transit (lookin’ at you, MTA) will reach unthinkable new heights once you ride Tokyo’s glorious Metro trains. Without exaggerating, they are absolutely f*cking spotless. I would literally eat my mother’s home-cooked lasagna off the floors of these trains and stations. It’s mind-numbing how one of the busiest cities in the world manages to keep its mass transit so clean.
Cleanliness aside, I can almost guarantee after just one day in Tokyo you’ll feel surprisingly comfortable using the Metro. The trains are very easy to navigate, and all stations and ticket machines are very English-friendly. The passengers (just like everyone else in Japan) are super polite and most stations have staff on hand to ask for assistance. Google Maps will become your BFF, making everything very easy, down to notifying you of which platform number to get on and off the train.
Tokyo takes pride in the utmost efficiency for pretty much everything, and the train system is no different. It’s extremely rare for a train to even be so much as one minute late. Could you imagine if those were the conditions of your morning commute? FML. A last important note: keep the ticket you receive upon entering the train and save it for when you exit the station. You will need to give it back on your way out in order to exit (or else you’ll have to pay the fee again).
Ubers and taxis are extremely expensive in Tokyo for reasons still unknown to me. I took an Uber just once in my time there and that was only because it was after the Metro’s operation hours (which BTW they stop running roughly around midnight). Ubers are not commonly used since the Metro is so accessible (and because the traffic in Tokyo is insane), but they are of course always an option.
Lastly, if you’re staying in the heart of Tokyo your hotel should only be about 40 minutes from the airport. It’s not a far drive, but it will still cost you anywhere from $275-$300 via Uber or taxi (absurd). Your best bet is to either take a bullet train to the metro or a bus, both of which run around $40 per person. And fret not! Because the almighty Google Maps will help you figure out the logistics of both options when you’re there. This transportation info seems dense, but it’s absolutely stuff you should know before you get there. I do a lot of research before I travel and did not come across much about this, so you’re welcome!
Kawaii Monster Cafe: During their last visit to Tokyo, The Kardashians created a lot of hype here (and the hype is very real). This place is without a doubt a tourist trap, but I absolutely loved it. It’s a well-executed, colorful, fun vibe from start to finish. Make sure you book your reservations a few weeks in advance, and insider tip: if you want to snag one of the cool booths, get there 5-10 minutes before the requested arrival time.
Teppan Baby: This place has it all: unreal food, excellent atmosphere, and reasonable prices. Sit at the hibachi-style grill for an intimate look at how your dishes are prepared and get friendly with the energetic chefs.
Kakekomi Gyoza: Enjoy dumplings galore at this no-frills Izakaya restaurant in the heart of Shinjuku. I ate eight vegan dumplings and could have eaten roughly 1,000 more.
Manten Sushi: “Sushi will never be the same after eating sushi in Japan.” —a direct quote I said to my husband during our 27-course Omakase sushi dinner at Manten Sushi. The sushi here is absolutely to die for, and the sushi chefs make your experience one to remember. Reservations are highly recommended if you’re looking to do it up Omakase style.
Mr. Farmer: Breakfast is oddly hard to come by in Japan. It’s almost as though they skip over breakfast entirely and just go right to lunch and dinner menus. Not to worry though—Mr. Farmer has a wide variety of brunch favorites you’re familiar with served in a gorgeous botanical dining room.
Robot Restaurant: It’s widely known as a “must-see”, but I have a weird love-hate relationship with this place (and mostly it’s hate). It’s a super tourist trap, but not in a good way. It’s essentially a bizarre, loud performance show that I don’t necessarily regret going to, but I don’t really recommend either. Whatever you do, absolutely do not eat here and just go strictly for the show (and prepare for things to get REAL weird, Tokyo style).
Aoyama Flower Market Tea House: Sip the tea in this tea house blooming with flowers and plants. Lines can get long here, so get here early for your breakfast tea.
Ginza District: Ginza is home to the world’s busiest intersection, so you can just imagine how crazy it is here. The skies are filled with skyscrapers and streets are filled with endless shopping. If your inner 6-year-old still has a burning love for Hello Kitty, check out Sanrio World.
Akihabara: This district is home to many video game and electronic stores, giving it the fitting nickname “electric town.” If you’re a vintage video game lover like myself, don’t forget to stop at Super Potato while you’re in the area. Arcades here are filled with colorful claw machines and Mario Kart games where they superimpose your photo onto your character as you play. (Okay I’m done being a nerd now.)
Harajuku: Takeshita Street is a whimsical shopping strip within Harajuku that feels like something straight out of Dr. Seuss. The shops are quirky and the food is colorful. The underground Purikira photo booths are a best kept secret to tourists on this strip, and will certainly give you a dose of Harajuku culture. The photo booths overly filter your face (in a fun, weird way) and the whole place bizarrely serves as a place to model your newly purchased clothes. After your Harajuku photoshoot, grab an oversized rainbow fairy floss at Totti Candy Factory (often imitated, never duplicated) and play with puppies at the Teacup Poodle Cafe. If this street isn’t what dreams are made of, then I don’t know what is.
Themed Bars in Shinjuku: The streets in this neighborhood are filled with never-ending neon signs, but the bar scene in Tokyo is generally very intimate and chill. Most are located on upper levels of buildings (which can be difficult to find at times) and consist of intimate settings where you sit and unwind as you drink (aka no dancing/raging). Having said that, the bars are all very unique and beyond enjoyable. Most bars in this area have odd themes at places like Maid Cafe, Ninja Shinjuku and Alice in Magical Land. There’s a theme for everyone here.
Definitely visit Magic Bar if mind-blowing magic is your thing and 8-Bit Cafe if you’re into video games with Japanese roots. (There I go being a low-key nerd again.)
Golden Gai District: This 70+ year-old district is made up of over 200 miniature bars that seat only 4-8 people, defining the very essence of minimalism. The intent is to encourage patrons to converse with one another, making for a very special experience.
Bar Orchard is a great place to grab a mixology cocktail. Select your favorite fruits from their beautiful display tower of real fruit and watch them craft you an out-of-this-world cocktail. What’s not to love?
Bar High Five is another wonderfully intimate bar with a great selection of Japanese whiskey.
Sensōji Temple: Tokyo’s oldest temple is a must-see site with crowds of people around the clock. It’s surrounded by hundreds of markets filled with fun souvenirs and endless sweet treats.
Shinjuku Gyoen National Garden: Feast your eyes on this little slice of peaceful heaven in the middle of Tokyo’s madness. The Japanese landscapes are unlike anything you’ve ever seen and the tranquility is untouchable.
Tokyo has a lot to see and do that will give you memories to cherish (and Instagram) for a lifetime. I can truly say that interacting with the amazing people of this city is something that’s changed how I think as a person. I encourage you to take a page out of their playbook and actually smile at people you encounter, engage in conversation at any chance you get, and of course, enjoy as much sushi as you can.
As I said, you can totally stretch out your time in Tokyo if you are able, but this was my itinerary if you are only there for a short trip:
Day 1: Arrival
☆Land and check into Hotel Wing International Premium Tokyo Yotsuya
☆Head right to Akihabara (“electric town”) to visit stores like Super Potato (a vintage video game store—closes at 8pm), the SEGA store (arcade games), and Tower Records
☆Head back to Shinjuku neighborhood for dinner at Teppan Baby Shinjuku and drinks at 8bit Cafe
☆Nightcap at Magic Bar for more food, drinks, and magic
Day 2: Sightseeing
☆Breakfast at Mr. Farmer
☆Take a 15-minute walk or train to the Shinjuku Gyoen National Garden
☆Visit Sensōji Temple—make sure to arrive before it closes at 5pm. (45-minute train ride from the gardens)
☆Dinner in the Golden Gai district at the landmark Omoide Yokocho alleyway for street food dumplings
☆9:30 reservation for the show at Robot Restaurant. It’s only a 7-minute walk from dinner, but arrive by 9pm.
☆Play Mario Kart next door at GAO Kabukicho arcade
☆Head to Shibuya district for drinks at Red Bar, The Room, or Ele Tokyo
Day 3: Shopping
☆Arrive early for breakfast tea at Aoyama Flower Market Tea House
☆Take a 10-minute walk or 5-minute train for your 11:30 reservation at Kawaii Monster Cafe for drinks and dessert. Arrive 15 minutes in advance for a good seat.
☆10-min cab ride to the Harajuku district for shopping and strolling. Walk through Takeshita Street, Tokyu Plaza, and Cat Street. Shop at Alice on Wednesday, WEGO, and Honey mi Honey. Snack on takoyaki at Gindaco and fairy floss at Totti Candy Factory.
☆30-minute train ride to the Ginza district for more shopping and sights. (Check out Sanrio World and Kabuki-za Theatre.)
☆Grab a small bite at the restaurants underneath Yurakucho train station for Izakaya
☆6pm dinner reservation at Manten Sushi
☆Drinks at Bar Orchard or Bar High Five are a 15-minute walk from dinner
Images: Joana Mascioli