Let's Get Nauti! The Official Bachelorette Guide To Annapolis, MD

Annapolis often gets passed over in favor of its bigger neighbors like Baltimore or Washington, D.C, but this Instagrammable waterfront town is the perfect destination for a nautical-themed bachelorette getaway. Take advantage of Annapolis at its prime and visit during the warmer months when you and the girls can hop on a boat and wander the cobblestone streets without worrying about those bulky winter coats. 

How To Get Around

The closest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI) in Baltimore where Amtrak also has a stop. From there, you can grab an Uber, rent a car, or hop on the SuperShuttle to make the 20-some mile trip to Annapolis. 

Opt to stay downtown in the historic district, which you can explore by foot, but don’t sleep on the water taxi service that cruises around the harbor in downtown Annapolis.

A ride on the trolley is also super cute. Local’s tip: Hop on the one-hour tour for a cruise through 350 years of history and you’ll see most of the top Annapolis attractions, including Victorian mansions, the Maryland State House, and the Naval Academy. 

Where To Stay

The downtown historic area is it if you are looking for walkability and a shit ton of charm. Think cobblestone streets, colonial homes, and a bustling city dock. 

Annapolis Waterfront Hotel

Aka, where Betches bride Nicole Pellegrino tied the knot. This luxe stay is a splurge, but worth every penny. All 150 rooms are decorated in chic nautical-inspired blue and white décor. Earn extra bridesmaid’s points by booking one of their 16 waterfront balcony rooms that overlook the downtown harbor and wake up every morning to swoon-worthy views of the Chesapeake Bay. Pusser’s Caribbean Grille serves Caribbean cuisine on-site for breakfast, lunch, and dinner, but we mostly like the easy access to Painkillers. See more on those below.

The Westin Annapolis 

We like this hotel because it’s also home to the Aveda spa, Varuna, which is a great place to get a blowout one night or pamper the bride-to-be with a massage. Of the 225 rooms, each features a view of either the city or the courtyard. There’s also an indoor pool. While it sits about one mile away from the downtown area, they do offer free shuttle service. 


This is the move, especially if you want more space or at least a kitchen for penis balloons and pregaming DIY brunches. You also have your pick when it comes to incredibly cute Airbnbs and VRBOs. From renovated row homes in the heart of the historic district to options as unique as this very chic houseboat, there are plenty of rentals for all kinds of budgets. 


Where To Eat And Drink 

Boatyard Bar and Grill 

Just on the other side of the Spa Creek Bridge is the community of Eastport. It was established in 1998 when the drawbridge connecting Eastport and downtown Annapolis was temporarily closed. The little neighborhood has its own feel and is def worth checking out. Go to “the Boatyard,” an airy, laid-back spot designed to look like the interior of a boat. We love the crab cakes and so do icons Cal Ripken Jr., Jimmy Buffett, and Michelle Obama, but they offer plenty of non-seafood options too, including an awesome chipotle black bean burger. The move: Start with a locally-brewed beer at Forward Brewing Company, a cute, low-key brewery that local’s love. Try the “Ceremonious Exchange” imperial porter that’s made with cold brew from Annapolis-based Ceremony Coffee Roasters.  

Metropolitan Kitchen & Lounge

We stan a boozy brunch and Metropolitan is it. On weekends, they offer unlimited mimosas with flavors like mango and blueberry and the ultimate brunch menu. Think Hangover Flatbread with gooey melted cheddar and perfectly fried eggs. That said, it’s also an awesome option for a casual dinner. It’s got a neighborhood hangout feel and a drool-worthy selection of small plates and craft cocktails. Order their fries and thank us later. Local’s tip: Request a table on their rooftop deck.

Vida Taco Bar

The vibe at Vida Taco Bar is chill, the margaritas are strong, and the tacos are fresh. What more could you ask for? Plus, nothing says “Let’s get this bachelorette weekend started” like tequila and homemade guac.

Lewnes’ Steakhouse

Though the family-owned business began as a tobacco, liquor, and ice cream shop back in 1921, it is now the go-to spot for a celebratory meal. The dim-lighting, leather, and high-booths make this place a total scene. Drool-worthy steaks are a la carte and the  vegetables and salads are served family style. Sure, beef is the star, but the menu also includes plenty of seafood options. Ask the knowledgeable servers about the more than 450 wines and they’ll help you out. Pro tip: Make this your classy dinner and go here on a night when you’re all dressed up. Take the water taxi over from the Annapolis side and make it a whole thing. 


Go to Pusser’s for their Painkillers (a strong mix of Pusser’s rum, cream of coconut, orange and pineapple juices with a sprinkle of nutmeg), but stay for the people watching. Located in The Annapolis Waterfront Hotel, this is a great place to grab a table outside on the dock. But remember to pace yourself. The Painkillers look like smoothies, but they hit harder than those tequila shots from spring break freshman year. 

What To Do

GameOn Bar & Arcade

GameOn is reminiscent of vintage arcades, which will make you feel like a tween again. Except there’s booze. Lots of it. The bar serves up the standard craft beers, wine, and cider, but also Cold Ass Beer on tap, boozy slushies, 21+ Capri Suns, Jell-O shots, and shareable-sized cocktails. The coin-operated arcade games range from skee-ball and Dance Dance Revolution to throwback options like pinball and Pac-Man. The food options are as retro as the entertainment with upscale Frito pies, hot pockets, and gourmet pop tarts. There’s also a large patio that hosts seasonal activities like cornhole and outdoor movie nights.

Get Out On The Water

I mean, did you even visit Annapolis if you didn’t do some sort of water activity? Not to worry. There are plenty of ways to do this. Test out your balance at Capital SUP. You can rent SUP boards and kayaks on the South River via Quiet Waters Park. They also offer private tours and SUP yoga classes. Annapolis Canoe & Kayak is another option, offering rentals on Spa Creek out of Eastport. 

If your group isn’t feeling a sweat sesh, then hop on a boat and let someone else do the work. Watermark offers a number of local tours from sightseeing cruises to daylong excursions from the Chesapeake Bay to St. Michaels, another historical town located across the Chesapeake Bay on Maryland’s Eastern Shore. Boat tours can last from 40 minutes to 7 1/2 hours and prices range from $22 to $99. 

For a full sailing experience, check out the 74-foot Schooner Woodwind. The sailing company’s two wooden schooners provide daily sails as well as a sunset and specialty cruises, including a brunch option that includes mimosas and Bloody Marys. The two-hour daily cruise sets sail four times a day, but these fill up so make sure to book in advance. 

Book A Wine Tasting

Uber out to Great Frogs Winery for an afternoon of wine tasting. Built on an old tobacco farm, the winery takes advantage of the area’s naturally sandy soil to grow French Bordeaux varietals. Try the white, rose, and red varietals and blends. When you’re finished, enjoy a picnic outside the tobacco barn and grab some photos in the vineyard.

Federal House

The club scene in Annapolis is nonexistent (that’s what DC is for), but there are a few bars that clear space for a dance floor and bring in a DJ on the weekends. Once the music gets started at Federal House, the atrium is filled with a young crowd twerking to the latest hits. This is the spot for those matching sailor hats and, most likely, really embarrassing stories  great memories for the next morning.

Lexi Weber
Lexi Weber
Lexi Weber lives in Annapolis, Maryland with her husband. She writes about relationships, sobriety, and mental health. Her work has been featured in Refinery29, Huffington Post, Shape, Cosmopolitan, & more.