Collected by Lara Dalinsky , AFAR Local Expert
410 Severn Ave, Annapolis, MD 21403, USA
The Harbor Queen is a fun way to familiarize yourself with the Annapolis' maritime history and experience what the city is famous for — boating. The 40-minute cruise on the iconic red and white boat gives passengers an informative, narrated tour...
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,...
410 Severn Ave, Annapolis, MD 21403, USA
Annapolis is known as the Sailing Capital of America. Yet even without a boat, it's possible to soak in the maritime action with a stroll along the harbor. A pleasant walk starts around the pier at the end of Dock Street in downtown. This is a...
175 West St, Annapolis, MD 21401, USA
The Metropolitan Kitchen and Lounge is a funky, eclectic restaurant that offers farm-to-table fare with a little bit of something for everybody. The restaurant has a variety of dining settings that range from an airy bar for drinks to an intimate...
723 2nd St, Annapolis, MD 21403, USA
While walking around the historic district in downtown Annapolis, I noticed that some buildings displayed curious Liberty Tree markers by their entrance in a variety of colors. I later learned from a local historian that The Historic Annapolis...
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...
234 Main St, Annapolis, MD 21401, USA
Brown Eyed Girl is a one-stop-shop for all things flirty and funky. When I visited the cozy store, I was surprised to find the boutique packed with women ages 16-60. Sure enough, I was drawn in too, purchasing an ombré tank and coral-inspired...
49 West St, Annapolis, MD 21401, USA
49 West is the quintessential coffee shop and cafe. Upon entering, I was greeted by a laid-back scene: a guitarist singing bossa nova in the corner, tables full of friends chatting, and walls walls dressed with local art. 49 West serves wholesome...
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 Main St, Annapolis, MD 21401, USA
During this digital age, Back Creek Books is a reminder of the dwindling art of the printed book. The store carries an impressive collection of quality, out-of-print military, naval and nautical books that will appeal to history buffs and...
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...
207 Main St, Annapolis, MD 21401, USA
Capital Comics is on of the most fun shops to visit in the heart of downtown Annapolis. The space is crammed with books, tees and toys that will captivate the young at heart. My husband, a self-professed nerd, was impressed by the store's...
55 West St, Annapolis, MD 21401, USA
The Annapolis Collection Gallery is devoted to showcasing historical black and white photography and the work of six contemporary Annapolis master artists: Moe Hanson, Roxie Munro, Greg Harlin, Ann Munro Wood, Sally Comport and Yoomi Yoon. The...
100 State Cir, Annapolis, MD 21401, USA
The Maryland State House is the oldest state capitol still in continuous legislative use. It is also the only state house to have served as the nation's capitol. This is a good starting point in Annapolis for introductions to Maryland history....
550 Taylor Ave, Annapolis, MD 21401, USA
Navy football is a mainstay for Annapolis in the Fall. College football draws some of the most passionate fans in the country, but Navy games draw upon the heraldry, pageantry and tradition of the U.S. Naval Academy. The entire city buzzes when...
43 Pinkney St, Annapolis, MD 21401, USA
While exploring a picturesque side street in downtown Annapolis, I noticed a sign that said "Hogshead," and "free entry." Upon entering, I was greeted by a living historian in colonial clothing. She guided me to an adjoining room filled with...
40 State Cir, Annapolis, MD 21401, USA
The Annapolis Pottery is a unique shop that sells pottery made by American artisans and also has in-house working studio where potters produce merchandise. The store's goal is to offer creative and functional artwork that can be integrated into...
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