How To Plan A Couples’ Weekend Getaway To The Hamptons That Isn’t Boring

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

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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

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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.

 

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“This slice of Americana gets even sweeter come fall.” Read more about why Baron’s Cove is the perfect getaway this fall and winter at @marieclairemag Link in bio.

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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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Dinner plans anyone? #toppingrosehouse #jeangeorges #longislandrestaurants #hamptonstyle

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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. 

 

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We are proud to host responsible social distancing. Facial covering masks are required when moving about the premises! Enjoy your evening….. Please arrive with your mask on. #compliance #masks #distancing #outdoordining #sanitize #safe

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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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Perfect Clam Bar weekend. This beautiful 📸 by @newyorkfoodbabes #lobsterroll #joinusforbreakfast #theclambar

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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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Stay Safe! Wear your masks, wash your hands, and socially distance! And while your at it, take in the view 😍

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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 🤎

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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. 

 

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🙌 and just like that- the weekend is upon us! It’s time to put on your white and drink all the pink 😉 . . . . . 📸: @roxyfoodiechronicles #duryeaslobsterdeck #montauk #duryeas #summer #mdw

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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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The family table. Tutto Sag Harbor. Tutto il Giorno. Tutto family. @urbanzen #uzxtutto

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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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Cooking up a very tasty opening… Join us THIS Thursday at 5pm! #mainstreettavern

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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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Breakfast is served. @chefjsmillie @marrammontauk 📷: @giadapaoloni

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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.

 

SoulCycle 

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

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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:

  1. Khanh Sports
  2. Amagansett Beach & Bicycle
  3. Dan’s Bike Rental
  4. Sag Harbor Cycle Company
  5. 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.

 

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Weekend Menu: Solved ✅ Order our Seafood boil by Thursday at 5pm and you could be eating this spread on the 4th. Available for delivery in The Hamptons or pick-up/delivery in NYC. Also comes with a bottle of @hamptonwater Rosé! Link in bio to order! 🐟🦐🦞🦀🇺🇸

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Image: Hamish Duncan / Unsplash; theroundtreeamagansett, thesurflodge, baronscove, toppingrosehouse, bridgehamptoninnandrestaurant, theclambar, navybeachmontauk, scarpettarestaurants, duryeaslobsterdeck, tuttoilgiorno, themainstreettavern, monstradormarram, wolfferwine, mareanyc / Instagram

The Ultimate Guide To The Hamptons, According To ‘Summer House’s Stephen McGee

Let me just start off by saying for those who don’t know: I am on the runaway hit, renewed-for-a-second-season show Summer House and there is a rumor that I started they want to nominate me for an Emmy, so you know everything in this article is completely true and a proven fact.

Memorial Day is upon us which marks the New Yorkers’ official start of 12 weeks of starvation summer. If you haven’t been prepping for this weekend for the last IDK… like eight weeks or so, you’re probably fucked, but you can still starve yourself all week and maybe Stassi can tell you where to get a turtleneck swimsuit. (Love you, Stassi.)

I’m going to assume you already have a place to stay or at least a place to crash or something. If you are looking for a summer house this late in the game you might as well give up unless you want to be on TV (wink).

There are some great hotels out East, but they can be expensive and if I started laying out how to get a sugar daddy this post would just get really long and I think I may be liable if something happens. You can figure it out though… I believe in you.

 Bridesmaids

There are four ways to get to the Hamptons and I’ll break them down in order of most to least desirable:

1. Helicopter: LIVE YOUR BEST LIFE. I’ve literally offered kidneys, livers, every organ (and I mean every) for an extra seat.

2. Car: By car I mean SUV because that can be a LONG ride. On a Friday, I’ve had the 90 mile drive take five and a half hours. The benefit is you can stop whenever and you are just with your friends. Tip: there is a Taco Bell like 20 miles in.

3. Bus: Luxury Liner is the best bus option. I mean it says luxury in the name and they offer free SmartWater and Skinny Pop. BYE.

4. Train: I’ve never felt more like an extra on the set of Slumdog Millionaire in my life. It’s crowded. It’s hot. Someone smells. And when you’re on that platform waiting, the real ugly side of people can come out in order to get a seat when those doors open.

Slumdog Millionaire

CONGRATULATIONS. You’ve finally made it. Hopefully you arrive and find your accommodations like this:

Summer House House

Believe it or not, I can be rugged sometimes, but the Hamptons is NOT one of those times you want to be adventurous unless it’s in the bedroom (Google “Sir Ivan’s Castle” if you’re brave). If you arrive anywhere with “RV” or “campground” in the name, scroll back up and reverse your travel ASAP.

Hopefully you have a good group you’re staying with, but also hopefully there is someone you can talk about behind their back because this is Betches. Hi.

I like to have a nice mix of good friends and the acquaintances—it keeps it interesting.

IMPORTANT: Do not bring anyone that you have been dating for less than two months. Things get stressful at times when you’re drunk and trying to figure out where you left your phone and everyone changes a little out East… this will definitely break your relationship. I learned this lesson on one of my first big trips to Montauk.

Stephen McGee Summer House

I had been going on like, regular dates with this guy and he was so hot. He had met my friends so I thought bringing him to a weekend in Montauk would be an amazing way to really make this a lasting relationship. The day after this photo way taken was the last day I saw him and if he happens to read this I have one message:

Go fuck yourself / if it’s after 3am you can text me.

IT’S TIME TO PARTY

First of all, Memorial Day Weekend is known for being like the box of chocolates of weather. It could be nice, sunny and amazing, but probably it will be kind of cold, overcast, and raining. At the time of me writing this, which is 3:30am and I’m drunk inspired, the weather is going to be complete shit. Bring your layers, because I don’t want to hear anyone complaining they are cold—and no, you cannot wear my jacket. I’m chivalrous, but we also have the weather app.

Second, if you are in East Hampton or Montauk, there is no Uber and you will literally want to kill yourself slowly with shards of empty rosé bottles unless you take this next piece of advice. Always have lots of cash for cabs and take out your phone right now and put this number in your contacts:

Montauk’s Best Taxi
631-668-8444

They are not paying me to do this… that’s just how much they saved my life last summer. One time the Wirkus Twins and I were literally crying trying to get a cab and it was complete chaos. Everyone was running to jump in when any cab pulled up, whether they called it or not. A Winklevoss twin was literally crawling on the ground across the parking lot (The lyrics of a Countess Luann song come to mind—you know which one). Montauk’s Best came and we met the driver and called him the rest of the summer. If you tell them Stephen from Summer House sent you, they are still going to take your money, but they will probably get you a car faster when you’re blacking out at 4am trying to get home.

Tired

BRING ON THE BOOZE

I swear you will hear the word “rosé” no less than 20,000 times in a weekend in the Hamptons, but do not feel obligated to drink it. Honestly, if you know that wine sends you over the edge, just do us ALL a favor and drink what you’re good at. The old saying “it’s a marathon; not a sprint” is even more appropriate when applied to drinking than it is even when you’re talking about actually fucking running after the sparklers in the club. Also, can we all agree to stop with Café Patron shots? So Meatpacking 2013…

Disclaimer: I have really only spent a lot of time in East Hampton and Montauk and I am so lazy a creature of habit so I go to a lot of the same places. But I am going to give you some places I love and some I don’t… just assume everywhere else is ok:

Likes

Surf Lodge: Quintessential Montauk. The bar can get very crowded, so buy multiple drinks at a time. Then cross over the dining patio and there is a swing and more secret seating.

Montauk Beach House: They’ve been stepping up their DJ game every summer, but also the pool scene is nice. It’s nice if you need to get away from your house during the day.

Gurney’s: Beach day bed. That’s all.

Jue Lan Club: Located in Southampton. If you’ve ever been to their Sunday brunch at the Manhattan location, you know they know how to throw a good party. The food is good and there is amazing art inside.

Meh

Liars: It’s like a late-night place in Montauk but I think it’s a doublewide trailer. It’s fine but I’ve never ended up there and not had drama amongst my friends later so I think it’s cursed and I just avoid it.

That place in East Hampton that feels like a tunnel: It used to be Finale East and SL. IDK what it is anymore but like the real problem is THERE ARE ONLY TWO TOILETS IN THE ENTIRE PLACE so do the math.

AM Southampton: Honestly it can be fun if that’s what you’re into, but like, you should have just stayed in the city if you want to go to a club.

At the end of the night, your sugar daddy you are going to spend a lot of money going out. I am more of a fan of house parties because I’m cheap and when I get tired I will go upstairs in some obscure room and take a nap to reboot. It’s the only time I’m more than happy to go back in the closet.

Just keep piling on the alcohol and you’re sure to have a good night/rough morning.

Whatever

OTHER THINGS YOU NEED KNOW

Other places in the world you can float around all day on cheap floats, but in the Hamptons you can actually find people who are snobby about floats (me). If you want to impress people on Instagram you have to shop FUNBOY, who just released a brand new batch of floats that are AH-FUCKING-MAZING.

Take a surf lesson/flirt with a surfer. It’s pretty fun and you can probably get three or four good TBT’s from it.

Sooth services the Hamptons so you can get a Sunday massage. #praisehim

Two Mile Hollow Beach in East Hampton is like an unofficial gay beach but it’s not like crazy Fire Island. I just describe it as the fun beach because it’s young and cool and everyone socializes… there are few children which is the biggest selling point. YOU CAN SEE CELEBRITIES THERE AND, NO, I AM NOT TALKING ABOUT ME. They are just like us when we are at the beach… sand in all the wrong places.

There is a Barry’s Bootcamp, Tracy Anderson, SoulCycle, etc. I’ve heard Switch and CYC are opening as well. You can sweat out last night’s tequila with a class in the morning and sometimes they will forgive you if you have to cancel because you’re too hungover of an emergency and credit you if you beg.

Wineries are fun but not really a party. Make sure you’re in the right mindset or you WILL get in a fight with your drunk friend.

Wine

Well, that’s pretty much the extent of my brain function tonight all the tips I have for you to take over the Hamptons this summer. If I think of more important information I’ll release a Volume II. Tweet me if you have any more tips, questions or success from any of these and follow me on Instagram and maybe I’ll run into you out East.