Things To Do Around Annapolis

The Best Restaurants and Activities to Experience the Night Before Your Annapolis Charter Vacation

Many of our charter guests choose to sleep aboard their charter boat the night before their Chesapeake Bay excursion. Make the most of your evening in Annapolis by visiting some of the most popular restaurants, bars, and shops in Eastport and downtown Annapolis.

When it comes to restaurants, there are many different options. Whether you’re chartering with a group of friends for a bachelorette party, having a romantic charter outing, or planning a charter vacation with your family, Annapolis is the spot for you!

Annapolis Restaurants

Harry Browne’s Restaurant – a mile drive across the Spa Creek Drawbridge to Waypoints Annapolis, Harry Browne’s Restaurant invites you to experience fine dining and award-winning cuisine in an elegant setting. Harry Browne’s is open for lunch, dinner, and Sunday brunch. Some of the top menu items include crab cakes, filet mignon, and seared sea scallops.

Federal House Bar & Grille – One mile across the Spa Creek Drawbridge from Waypoints Annapolis, Federal House is known for its signature sandwiches, fish & chips, and crab cake dinner. The bar section of the restaurant has a wide variety of local beers, including Guinness Blonde, FedHead Golden Ale from Union Craft Brewing Company, and more! They also offer a variety of happy hour specials that are updated weekly.

Boatyard Bar & Grill – Two blocks from Waypoints Annapolis, Boatyard Bar and Grill has been family-owned and operated since 2001. Their goal is to pay tribute to the sailing and fishing lifestyle of the Chesapeake Bay. They are known for their award-winning hand-made crab cakes made fresh every day using only the freshest and finest jumbo-lump crabmeat.

Dock Street Bar & Grill – Just a short sail across Spa Creek, Dock Street is well known for its crab cakes and extensive beer and cocktail selection. Dock Street is also known for being a home away from home for the local Midshipmen at the Naval Academy right down the street. Their motto is “proud to serve those who serve.”

Pusser’s Caribbean Grille – Five blocks from Waypoints Annapolis, Pusser’s is a lively waterfront restaurant in Downtown Annapolis that is consistently awarded the best in dockside dining. This fantastic restaurant features live music at the dock on weekends. Pusser’s offers fresh Chesapeake Bay seafood and a large selection of tropical drinks, including the famous Painkiller.

Annapolis Nightlife Hotspots

When it comes to nightlife, there are so many options to choose from. Some of the most popular places in Annapolis include:

O'Brien's Oyster Bar

O’Brien Oyster Bar & Seafood Tavern – One mile from Waypoints Annapolis, O’Brien’s has been serving fresh cuisine and cold beverages since 1999. From crabcakes to oysters, this restaurant showcases the best seafood that the Chesapeake has to offer. For those of you that are music buffs, make sure to visit O’Briens, starting at 10:30 p.m., on Fridays or Saturdays to enjoy some live music!

Galway Bay Irish Restaurant and Pub – Just three blocks from Waypoints Annapolis sits one of the best Irish pubs in the area. Visit Galway Bay on Fridays and Saturdays to enjoy a pint of Guinness and Irish curry fries while you listen to live traditional Irish music.

49 West

49 West Coffeehouse, Winebar, & Gallery – One mile across the Spa Creek Drawbridge, 49 West brings art, music, and community together with great food and drinks. The ambiance is inspired by the traditional European coffeehouse with an intimate listening room where they present local live music every night. Some of the genres presented include jazz, American roots, folk, indie, and classical artists. Make sure you reserve your table ahead of time to avoid the lines!

Contact us today with any questions about things to do before or after your charter vacation. We look forward to seeing you soon!