Local's Guide to History & Food in Annapolis, MD
Arts & Culture
Food & Wine
I grew up in this unique waterfront town and still visit a few times a year. I love that Annapolis feels different during each season, but my favorite time of year is October, when you're surrounded by crisp air and autumn colors during the annual boat shows. There are plenty of great restaurants, bars and boutiques in walkable downtown, many with live music nightly. Don't miss out on getting live steamed blue crabs by the dozen — locals won't mind teaching you how to open and eat!
The Fora Difference
Book with Jessica to access exclusive perks and experiences on your trip.
Free upgrades, spa credits and more—we got you
Customized travel planning for your style
Expert advice from people who’ve actually been there
Where to stay
134 Prince - Luxury Boutique Hotel
Classic Annapolis hotel with contemporary touches steps away from the U.S. Naval Academy, award-winning Annapolis restaurants and charming local boutiques.
Annapolis Waterfront Hotel, Autograph Collection
Waterfront hotel on the Annapolis harbor providing uncommon luxury with redesigned rooms, upgraded amenities, personalized service and breathtaking views.
Navy campus-style hotel with meticulous details that give it a stylish edge within its luxurious rooms.
Unlock perks by contacting Jessica to book your trip.
Day 1: City Dock & Ego Alley
Shopping and antiquing on Maryland Avenue — grab coffee from Old Fox Books, walk Main Street and State Circle, see first peacetime Capitol of the United States, which is the oldest state house in the country (1779) still in legislative use and has the oldest and largest wooden dome of its kind in the US.
Take a post-dinner walk past all of the generic ice cream shops and grab a scoop at Annapolis Ice Cream Co. at the top of main street (they have killer pie and cobbler flavors).
Day 2: On the Water
Take a morning walk through the Naval Academy — check visitor requirements/ID here. You could spend an hour or a whole morning exploring, and be sure to visit the museum if you have an interest in naval history.
Book a sailing tour on the Schooner Woodwind you can help hoist sails or just sit back, relax and enjoy the scenic views of the Chesapeake Bay.
Head to Vin 909 in Eastport for a casual dinner. They don't take reservations so arrive early or expect a wait, but you can enjoy a (very) reasonably priced bottle of wine in the garden while you wait OR depending on the season, head to Cantler's Riverside Inn for the area's best steamed blue crabs.
Check the calendar at Rams Head On Stage, a small cabaret style music venue, for local and national acts.
Head back to main street and enjoy a bourbon cocktail at Dry 85.
Get in touch with Jessica
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.