Annapolis for Couples
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.
801 Chase St, Annapolis, MD 21401, USA
Carve out some time to catch tenors and sopranos belt it out at Annapolis' Opera House. Founded in 1972 by a group of local artists, Annapolis Opera has been hosting staged operas and theater shows as well as concerts for over 40 years. Past...
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...
310 Third St, Annapolis, MD 21403, USA
If you're looking for a classic fine dining experience and you've got the wallet to match it, head over to O'Leary for some exquisite seafood. We're talking grouper, sole, rockfish, barramundi, swordfish, yellowfin tuna, and other types of fish...
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...
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...
273 Hilltop Ln, Annapolis, MD 21403, USA
Truxton Park is Annapolis' main city park and it spans over 80 acres of green space with hiking trails, a skate park, sections for picnics, and two playgrounds for kids alongside 12 tennis courts, three baseball fields, five basketball courts, and...
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...
300 Second St, Annapolis, MD 21403, USA
If you're looking for a quiet romantic spot for dinner with stunning views of the harbor while digging into fresh seafood from the Chesapeake Bay and Atlantic Ocean, Chart House should be on your radar. Though you can walk over from the historic...
1 Park Pl, Annapolis, MD 21401, USA
To sate those pasta cravings, Carpaccio Tuscan Kitchen's menu is inspired by Southern Italian flavors—from fresh Mozzarella di Bufala (Buffalo Mozzaralla) flown in from Italy every week and served with heirloom tomatoes, fresh basil, and extra...
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...
145 Main St, Annapolis, MD 21401, USA
French-inspired Lilac Bijoux is an artisan boutique run by Fern and Beth who sell exquisite, urban chic, and vibrant jewelry—chains, necklaces, earrings, bracelets, rings—designed by local and national artists. You can also buy their intricate...
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...
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...