A Day in Annapolis: Boats, Bites, and Bay Views
Maryland flag in downtown Annapolis
Annapolis made Travel + Leisure’s list of the top 15 best places to live - right up there with small, walkable gems like Santa Fe - and I can totally understand why. Just an hour from DC or Baltimore, it feels like a true escape from city life. In one weekend (or even one afternoon), you can hop on a boat tour, stroll through charming history museums, tour the Maryland State House, and sit down for some of the best seafood around.
Places to stay
The Annapolis Waterfront Hotel, an Autograph Collection Marriott property is, as the name suggests, right on the water in downtown Annapolis close to sights, the harbor, and plenty of great places to eat. This is the best option if you want to be near the water and if you prefer the amenities a larger hotel offers as an alternative to many of the smaller bed and breakfast or boutique hotels Annapolis features. (The Graduate is another option if you’d like to be in the arts district rather than by the harbour.)
If you prefer more boutique options, here are two sets of choices:
Historic Inns of Annapolis have three properties to choose from if you’re interested in a history lesson as part of your stay: Maryland Inn, Governor Calvert House, and Robert Johnson House.
Severn Grover Hospitality Group has several small hotels with similar historic architecture on the outside, but more modern design on the inside, if this is your preferred style: Gibsons Inn at Gate One, the Flag House Inn, 134 Prince, 86 State Circle, and 1313 West (this last one a bit farther out from the historic center of downtown).
Where to eat
Great seafood is plentiful here! If you want to both tour and eat, take the walking Historic Annapolis Food Tour. Try Choptank on the water for a lively, energetic experience at this popular waterfront restaurant and bar.
In the Arts District, Leo has impeccable customer service, a commitment to addressing the invasive snakehead fish by serving it up for dinner, and great $7 cocktail happy hour deal at the bar - all night Monday through Thursday and from 4 to 6 pm Friday and Saturday.
Near Leo, the Sailor Oyster Bar has warm and friendly staff, a wide selection of oysters, caviar that’s (relatively) reasonably priced and delightful crudos, such as the escolar crudo shown below.
More eating options just over a small bridge from downtown (near the Annapolis Waterfront Hotel) into Eastport, home to a marina, plenty of shops, and several additional dining options.
Rumhouse: Caribbean dining if you’re ready for an alternative take on seafood in a charming setting, both inside and on the patio.
Carroll’s Creek Cafe: Traditional seafood on the waterfront with marina views.
Boatyard Bar and Grill: Award winning crab cake served in this martime themed restaurant, with a popular and lively bar and outdoor space.
Blackwall Hitch: Casual bar scene with live music on weekend nights and Sunday brunch on the rooftop deck.
Things to do
Start at the Annapolis Visitor Center. There’s an enormous amount of information inside and the volunteers working there are knowledgable and helpful. If visiting for the day, you can park your car here and venture down to the harbour or over to the arts district, an 8-10 minute walk to either.
Next go to the Museum of Historic Annapolis. This is a starting off point to learn an initial history of the town and about many other small museums to check out.
Visit the Paca House and Garden. For just $5 you can tour both the small museum and expansive gardens.
Visit the Maryland State House and the statues in front honoring Thurgood Marshall and his legacy of the Brown vs. Board of Education ruling to desegregate schools.
Walk around and shop the boutiques, take in the sights, and enjoy the mural art and sculptures of downtown Annapolis.
If your group wants to experience the above in downtown Annapolis plus tour the Naval Academy, try the Annapolis Historic Walking Tour at Harbour and Naval Academy.
Getting Around
It’s easy and free! You can walk most places, and if not, you have the options of a free shuttle, a free e-shuttle, or a water taxi!
