Ranked by CNN as one of the top five towns to visit in America, there’s no escaping the charm of Annapolis. Once the capital of the United States and now known as the capital of sailing, the Maryland town is positively brimming in history.
With a busy waterfront made for leisurely cruises on the Chesapeake Bay, the maritime town boasts a vibrant dining scene heavy on seafood and Old Bay. You’ll also find a rich network of museums and cobblestone streets filled with art and stories of the past.
Roughly an hour from Northern Virginia, Annapolis makes for an ideal weekend trip, especially when summer is still in its full glory. Here’s how to spend a weekend in Annapolis.
Learn About the Town’s History
Annapolis has a long and storied past. And understanding some of the benchmarks of the town’s history will help you appreciate its present. Start at the Museum of Historic Annapolis for a compelling introduction to the city through the stories of Annapolis residents over the last 400 years. To further dive into the city’s maritime past, stop by the waterfront Annapolis Maritime Museum. The compact museum is worth a stop before heading out on the water.
The Banneker-Douglass-Tubman Museum is dedicated to preserving and sharing Maryland’s African-American heritage and culture from 1633 onward. Check out the museum’s Black History 365. The digital experience uncovers the stories and lives of generations of Annapolis residents from the African Diaspora through interactive videos and articles.
Sail the Chesapeake
No visit to Annapolis is complete without a sail on the Chesapeake Bay. Book yourself a ride on the Wilma Lee, one of the last remaining skipjacks in Annapolis. (It’s amazing that there used to be over 1,000 in the port city). Daytime sails are roughly two hours long and include a guide who peppers the journey with historical and cultural facts. For something more intimate, Darling Charters offers highly customized jaunts around Annapolis’s waterways, complete with Pinterest worthy charcuterie spreads and wine.
Tour the Naval Academy
Annapolis is, of course, home to the United States Naval Academy. Visitors can take a 90-minute walking tour of the scenic campus. The tour leads you through the academy’s grounds and provides a behind-the-scenes view of naval history.
Explore the Street Art Scene
Murals have been popping up throughout Annapolis, adding an interesting and thought-provoking juxtaposition to the town’s historic streets. The organization Future History Now offers self-guided walking tours of the city’s murals. Highlights include The Equal Justice Under the Law Mural (156 South St.) of Supreme Court justices Ruth Bader Ginsburg and Thurgood Marshall; Carr’s Beach Mural (on West Street near Westgate Circle), which memorializes a bygone resort and concert venue that catered to the African American community in the 1930s through 1960s; and the Breonna Taylor mural (14 Dorsey Ave.), a memorial designed to be viewed best via satellite.
Where to Eat
Seafood rules the culinary scene in Annapolis, and for good reason, its fresh and local. Stop by Leo, where broiled oysters, crab soup, and local catches like snakehead from the Susquehanna River and blue catfish from the Chesapeake Bay are the stars of the show. The old-school classic, Chick & Ruth’s, is a must-visit for its all-day brunch menu and some would say Maryland’s best crab cakes. Across the street you’ll find Preserve, which makes its own pickles and olives. For an indulgent mid-afternoon break, book an afternoon tea at the charming and historic Reynold’s Tavern, which has been operating since 1747.
Where to Stay
The Graduate hotel offers the comfortable rooms and playful touches the boutique chain has become known for, with some very Annapolis touches thrown in. (Chances are you’ll find a jar of Old Bay in your room.) For something more home-like than hotel-like, check out the brand new 86 State Circle. The nine room boutique hotel is housed in a historic 19th century building right in the heart of town.
Feature image courtesy SeanPavonePhoto/stock.adobe.com
