Annapolis trips and vacations
With a rich maritime heritage, Annapolis proudly calls itself ‘America's Sailing Capital.’ It's home to the United States Naval Academy and Chesapeake Bay, a sailing playground. Maryland is one of the original 13 colonies, so your vacation in Annapolis will give you a glimpse into America's storied past. And when the history lesson is over? Indulge in the bay’s famous blue crabs and unwind on sandy beaches.
The best neighborhoods in Annapolis
Downtown
Experience the city’s history in Downtown Annapolis. Step out of your hotel and stroll down streets lined with 300-year-old red-brick buildings. Visit the Maryland State House, the oldest US state capitol still in use. Check out the United States Naval Academy, which is open to the public, before exploring historic ships in Annapolis Harbour. You can even stay in inns that were once regular stops for signers of the Declaration of Independence.
Good for: History, architecture, harbor
Eastport
Take a water taxi across Annapolis Harbour and you’ll find yourself among the waterfront developments of Eastport. Dine out with a view of Chesapeake Bay from the marina, where you can try Eastport’s renowned oysters in some of the city’s best seafood restaurants. Rent a canoe or kayak, or learn to sail at the Eastport Yacht Club. The area is also home to Annapolis Maritime Museum & Park.
Good for: Waterside dining, seafood, water sports
West Annapolis
To the northwest of the historic city center, West Annapolis is an oasis of leafy streets and beautiful scenery. There aren’t many big hotels in this neighborhood, so it’s a great place to stay if you’re looking for a more local experience. You’ll find suburban vacation homes to rent in this quiet and exclusive part of the city overlooking the River Severn.
Good for: Riverside views, community feel, vacation homes
Things to do in Annapolis
Some of the best things to do in Annapolis revolve around the water. Explore the historic downtown streets then hit the seafood restaurants of Eastport and the beaches of Chesapeake Bay.
Places to eat
From blue crab to rockfish, Chesapeake Bay serves up a seafood bounty and Annapolis restaurants proudly present it. Head to Severn Avenue in Eastport (also known as ‘Restaurant Row’) to feast on crab cakes, lobster rolls and freshly shucked oysters. Rather a juicy piece of ribeye? This popular waterfront strip has steakhouses too.
Shopping
Main Street was graced in centuries past by legendary American figures like George Washington and Benjamin Franklin. These days, the city’s most historic thoroughfare is where you’ll find some of the best shopping. Browse for your next yachting outfit in boutiques, pick up nautical-inspired art or grab a souvenir from a gift shop. Annapolis Harbour Center also has a good mix of shopping.
Beaches
Annapolis isn’t directly on the coast, so it doesn't have beaches in the traditional sense. However, Chesapeake Bay and its tributaries have some great spots for swimming and water sports. Sprawl out on the beach of Sandy Point State Park, across the Chesapeake Bay Bridge. Mayo Beach Park on the South River also has a sandy stretch that’s popular with families.
