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 vibrant around Annapolis Harbor and City Dock, the heart of the historic district.

For first-time visitors, a guided tour of the city is an excellent way to cover significant ground. In true Annapolis fashion, there are plenty of options to explore 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 gaining insights into 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. For those who prefer staying on land, a 60-minute trolley tour leads you around the charming streets, marinas, and high points of the city.

Access to the U.S. Naval Academy might be limited, but it’s a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center.

If you prefer exploring on your own, stroll down brick-paved Main Street and explore its shops, art galleries, restaurants, and bars. Just a block away, you’ll find State Circle and the Maryland State House, the only state house that has served as the nation’s capital and is 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. Notable murals include the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) and the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local figure known for his community service; these murals can be appreciated via a self-guided walking tour.

Annapolis Hotels

Reflecting the city’s charm, Annapolis’s best hotels have nautical themes and nods to the local history. The Graduate Annapolis, which opened in the arts district in 2019, features decor inspired by Chesapeake blue crabs, Naval Academy colors, and vintage plaid. As its name implies, the Annapolis Waterfront Hotel, Autograph Collection, is conveniently located by the harbor and is just a short walk to the Naval Academy. The Historic Inns of Annapolis comprise three landmark buildings: Maryland Inn, Robert Johnson House, and Governor Calvert House, each blending 18th-century architecture with modern amenities (including free Wi-Fi).

Where to Eat and Drink in Annapolis

The culinary scene in Annapolis goes beyond seafood — however, if you’re visiting Maryland during the summer months, oysters and blue crab should certainly be on your dining agenda at some point during your trip. For a traditional Maryland crab experience, consider dining at Cantler’s, Mike’s Crab House, or The Choptank. Chick & Ruth’s has been a local favorite since the 1960s, while Iron Rooster offers a popular all-day breakfast menu. After dinner, treat yourself at Annapolis Ice Cream Company, known for homemade flavors like Funfetti cheesecake and birthday cake.

To step back into Annapolis history, visit Reynolds Tavern and 1747 Pub, where traditional English afternoon tea awaits you. The tavern’s cellar pub (watch your head!) offers refreshing Pub Punch or lager, and the beer garden welcomes guests during warmer months. For those seeking a modern vibe, options like Preserve for cocktails, Fox’s Den for craft beer and pizza, or Galway Bay Irish Restaurant and Pub offer lively dining spots on Maryland Avenue.

Best Time to Visit Annapolis

Like most parts of Maryland, Annapolis is a true four-season destination. The warmer months, however, are perfect for enjoying outdoor activities on the water. Spring typically marks the best time of the year to visit Annapolis, as summer attracts more visitors with the sailing season picking up momentum.

Getting There

Annapolis is easily explored on foot, although a car may be necessary if you wish to venture further into the Chesapeake region. Washington, D.C. and Baltimore are both about an hour’s drive away, depending on traffic. Therefore, 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) — places you within convenient driving distance of Maryland’s capital.