The Sailing Capital of the U.S. Is a Perfect East Coast Getaway — With Historic Charm, Tasty Seafood, and Scenic Harbor Views (2024)

The famous “crab cakes and football” line from “Wedding Crashers” may have firmly planted itself in the cultural zeitgeist 18 years ago, but there’s a lot more to Maryland than seafood and sports (although those are pretty important, too). Given its East Coast location and proximity to the Chesapeake Bay, many of Maryland’s towns and cities have waterfront access —hence, the association with the fishing and crabbing industries as well as sailing and other maritime activities.

As one of the original 13 colonies, Maryland was also influential in the shaping of the United States; in 1791, the state transferred ownership of a portion of its land to the federal government to form the country’s new capital, Washington, D.C.

There’s perhaps no city that combines everything Maryland is known for —food, culture, and historical significance — quite like Annapolis. Home to the U.S. Naval Academy, a walkable downtown, and a robust sailing community, the state’s capital is perfect for a long weekend away or an extended visit to the Chesapeake region.

Best Things to Do in Annapolis

With a nickname like the "Sailing Capital of the U.S.,” it should come as no surprise that Annapolis plays host to various water-adjacent activities. The warmer months are particularly buzzy around Annapolis Harbor and City Dock, the heart of the historic district.

If you’re visiting for the first time, a guided tour of the city is your best bet to cover as much ground as possible. In true Annapolis fashion, there are plenty of options to see the area by boat. Visitors who come aboard the Harbor Queen will explore Annapolis Harbor and cruise by the banks of the Naval Academy while learning about the city’s history and geography (tours are available from April through October). The Annapolis Maritime Museum & Park also offers Skipjack history tours that provide additional information about the Chesapeake Bay and its ecology. Travelers who don’t quite have their sea legs can opt for a 60-minute trolley tour around the charming streets, marinas, and high points of the city. Access to the U.S. Naval Academy is limited, but it’s certainly a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center.

If you prefer to discover a new place on your own, be sure to walk down brick-paved Main Street and pop into its shops, art galleries, restaurants, and bars. One block away, you'll find State Circle and the Maryland State House, the only state house to have served as the nation's capital and the oldest state capital in continuous legislative use. Further out in the Annapolis Design District — about two miles from State Circle —numerous murals decorate the city. From the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) to the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local who spent 40-plus years cleaning up the trash from Annapolis streets, these murals can be appreciated via a self-guided walking tour.

Annapolis Hotels

Like the city itself, the best hotels in Annapolis have touches of nautical whimsy and nod to the city’s history. Graduate Annapolis opened in the arts district in 2019 with decor “inspired by Chesapeake blue crabs, Academy colors, and old-school madras plaid.” Like other Graduate hotels, the property proudly celebrates the culture of local colleges — the U.S. Naval Academy and St. John's College. As its name suggests, Annapolis Waterfront Hotel, Autograph Collection, is conveniently located by the harbor, and it’s just a short walk to the Naval Academy. Historic Inns of Annapolis is made up of three landmark buildings in the downtown area: Maryland Inn, Robert Johnson House, and Governor Calvert House. Each house pairs 18th-century details and quaint ambiance with modern amenities (including free Wi-Fi).

Where to Eat and Drinkin Annapolis

The culinary scene in Annapolis goes above and beyond seafood —but if you’re visiting Maryland in the summer months, oysters and blue crab should make it into your diet at some point during your trip. For a taste of a traditional Maryland crab house, there’s Cantler’s, Mike’s Crab House, or The Choptank. Chick & Ruth’s has been a city staple since the 1960s, and Iron Rooster has a popular all-day breakfast menu. For a post-dinner sweet treat, head to Annapolis Ice Cream Company, where you can indulge in homemade flavors like Funfetti cheesecake, blueberry strudel, and birthday cake.

If you want a heaping dose of Annapolis history, add Reynolds Tavern and 1747 Pub to your itinerary. You’ll take a step back in time when you enter the tavern for traditional English afternoon tea or the cellar pub (watch out for the low ceilings) for a refreshing Pub Punch or lager. The beer garden behind the tavern also welcomes guests during the spring, summer, and early fall. For something a bit more modern, there’s Preserve for co*cktails, Fox’s Den for craft beer and pizza, or Galway Bay Irish Restaurant and Pub, a lively pub on Maryland Avenue.

Best Time to Visit Annapolis

Like most other parts of Maryland, Annapolis is a true four-season destination. The warmer months, however, are ideal for adventuring out on the water. Spring is typically the best time of the year to go to Annapolis, as summer tends to become busier when sailing season kicks into high gear.

Getting There

Annapolis can easily be explored on foot, but you’ll need a car if you want to venture further into the Chesapeake region. Washington, D.C. and Baltimore areboth about an hour’s drive away, depending on traffic, so flying into any of the area’s three international airports — Baltimore-Washington International Thurgood Marshall Airport (BWI), Washington Dulles International Airport (IAD), and Ronald Reagan Washington National Airport (DCA) — puts you within driving distance of Maryland’s capital.