Known as America’s Sailing Capital, Annapolis pairs a beautifully preserved colonial waterfront with the campus of the U.S. Naval Academy, making it one of the most historic port towns on the Chesapeake Bay.

Why Visit Annapolis

Annapolis offers a rare walkable blend of colonial-era architecture, active sailing culture, and Maryland’s state capitol, all centered around a lively waterfront lined with seafood restaurants.

Top Experiences

  • U.S. Naval Academy: Take a guided tour of the historic campus, including the Naval Academy Chapel and the crypt of John Paul Jones.
  • Annapolis City Dock: Wander the waterfront, watch sailboats come and go, and browse shops along this historic harbor.
  • Maryland State House: Visit the oldest state capitol still in legislative use, dating back to 1772.
  • Chesapeake Bay Sailing Tour: Book a sailing excursion on the bay for classic views of the Annapolis skyline from the water.
  • Historic District Walking Tour: Explore cobblestone streets lined with 18th-century homes in one of the best-preserved colonial districts in the country.
Annapolis Historic Walking Tour: Harbor and Colonial Downtown

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

★ 5.0 (47)
From USD 235
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Tipsy History Tour: 300+ Years of Annapolis Drinking History

Tipsy History Tour: 300+ Years of Annapolis Drinking History

★ 5.0 (47)
From USD 39
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Annapolis Chesapeake Bay Bridge Cruise

Annapolis Chesapeake Bay Bridge Cruise

★ 5.0 (2)
From USD 46
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America 250 Annapolis Walking Tour

America 250 Annapolis Walking Tour

★ 5.0 (2)
From USD 235
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Spirits and Spirits Haunted Walking Tour and Boat Cruise

Spirits and Spirits Haunted Walking Tour and Boat Cruise

★ 5.0 (1)
From USD 52
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Colonial Annapolis and Maryland State House Walking Tour

Colonial Annapolis and Maryland State House Walking Tour

★ 5.0 (2)
From USD 26
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Practical Tips

  • Naval Academy tours require photo ID and advance reservations during peak season.
  • Try Chesapeake Bay blue crab at one of the waterfront restaurants near City Dock.
  • Free parking is limited downtown, so consider the Gotts Court or Hillman garages.

FAQ

What is Annapolis known for?
Annapolis is known as the U.S. Naval Academy’s home, its colonial architecture, and its status as America’s Sailing Capital.

Can visitors tour the Naval Academy?
Yes, guided walking tours are available for the public, though visitors need a photo ID to enter.

Is Annapolis a good day trip from Washington DC?
Yes, Annapolis is about a 45-minute drive from Washington DC, making it an easy day trip.