Annapolis with Friends
Collected by Calliope Gianpoulos , AFAR Local Expert
For a quintessential snapshot of colonial history alongside vibrant waterfront views, fresh seafood, and thousands of sailors at the US Naval Academy, head to Annapolis, and experience Maryland’s nautical flair and historical significance.
1 Dock St, Annapolis, MD 21401, USA
You can get a quick taste of nautical life around Annapolis Harbor and the Chesapeake Bay with a 40-minute Watermark riverboat cruise. Once aboard the iconic red and white "Harbor Queen" riverboat, you get a narrated guided tour that includes...
Parole, MD, USA
About a 15 minute drive from Annapolis waterfront is the farmer's market where you can sample some of the region's freshest produce. Open on Tuesdays and Saturdays from April through mid December, you'll find over 50 vendors selling a wide variety...
33 West St, Annapolis, MD 21401, USA
Ram's Head On Stage and its neighbor, Ram's Head Tavern, are favorites for Annapolitans. It's an intimate venue for seeing live bands and acoustic acts. Because the space is fairly small, concert-goers are sure to experience their favorite artists...
13 Francis St, Annapolis, MD 21401, USA
Considering Annapolis was established in the 17th century, you can pretty much bet that it's a city steeped in history, with tales of ghosts and troubled spirits. Annapolis Tours and Crawls has been leading travelers through the city's back alleys...
84 Franklin St, Annapolis, MD 21401, USA
To learn more about Maryland's African American heritage, head over to the Banneker-Douglass Museum which is housed in a 19th century Victorian-Gothic building. It's permanent exhibition, "Deep Roots, Rising Waters," chronicles African American...
400 4th St, Annapolis, MD 21403, USA
Think of your typical fisherman's shack on steroids, and you've got the vivaciously family-friendly Boatyard Grill & Bar. You can mingle with local sailors and fishermen over the yard's seafood and raw bar which includes seafood dips, smoked fish,...
69 West St, Annapolis, MD 21401, USA
Level is a local gem located on West Street. The restaurant has the reputation for serving excellent hand-crafted cocktails and tasty small plates. The cuisine is inspired by the Chesapeake and Mediterranean. In celebration of the community...
51 West St, Annapolis, MD 21401, USA
From the "Metropolitan" sumo roll, which is tuna, shrimp tempura, avocado with creamy spicy and eel sauce in a soy wrap, to the "Miami" roll, which is yellowtail topped with scallion, avocado, srirracha sauce in a soy wrapper or just straight up...
1 Park Pl, Annapolis, MD 21401, USA
If French toast made with Challah bread dipped in an almond-scented egg mix, stuffed with coconut cream cheese and flaked coconut, garnished with diced strawberries, and dusted off with cinnamon and powdered sugar isn't enough to entice you into...
1 Riverview Ave, Annapolis, MD 21401, USA
With a long line of 48 taps spewing out a variety of brews and beers alongside 10 HD TVs for catching the latest baseball, football, or basketball games, Heroes Pub is definitely one of the local favorite sports bars in Annapolis. You're also find...
Compromise St, Annapolis, MD, USA
The FreshFarm Market is ideally located on the downtown waterfront. You'll discover a mouth-watering selection of fresh produce, bread, meats and other local goodies from the Eastern Shore. Vendors often hand out samples and are happy to share...
194 Green St, Annapolis, MD 21401, USA
Funky meets fun creativity at Hobo Bags where local Maryland artist and leather goods designer Koren Ray has followed in her mother Toni's footsteps to keep the international brand alive for over 20 years. Travel back to the seventies at Hobo...
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