Annapolis, Maryland · City Break
The sailing capital of America
Colonial streets, the Naval Academy & the Chesapeake Bay
Why Annapolis
Maryland's capital, on the water
Founded in 1649 and briefly the capital of the fledgling United States, Annapolis sits where the Severn River meets the Chesapeake Bay. Its Historic District, one of the largest collections of 18th-century buildings in the country, radiates out from State Circle and City Dock, with the US Naval Academy, the Maryland State House and a working harbour all within a ten-minute walk. Pair a few nights here with Washington DC, Baltimore or the Eastern Shore for one of the most characterful short breaks on the East Coast.
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Top things to do in Annapolis & Anne Arundel County
Highlights drawn from Visit Annapolis, the official destination organisation for Annapolis and Anne Arundel County, tell us which appeal and we'll fold them into your itinerary.
Explore historic downtown Annapolis
Maryland's capital is a 'museum without walls', four centuries of architecture, brick sidewalks and boutique shops radiating from the circular State Circle and Church Circle.
Tour the US Naval Academy
The 338-acre 'Yard' on the Severn River, Bancroft Hall, the Chapel crypt of John Paul Jones, the Naval Academy Museum and the noon formation of the Brigade of Midshipmen.
Visit the Maryland State House
The oldest state capitol in continuous legislative use in the USA, where George Washington resigned his commission in 1783 and the Treaty of Paris was ratified, ending the Revolutionary War.
Get on the water in Annapolis Harbor
Sunset schooner sails on the Woodwind, Wednesday Night Sailboat Races, kayak tours of Spa Creek and water-taxi hops from City Dock to Eastport, Annapolis is the sailing capital of America.
Walk the America250 Exploration Trail
A self-guided route through Annapolis and Anne Arundel County, waterfront landmarks, historic streets, the Kunta Kinte–Alex Haley Memorial at City Dock and stories of the revolutionary era.
Eat Chesapeake blue crabs
Steamed blue crabs and Old Bay by the bushel at Cantler's Riverside Inn and Boatyard Bar & Grill in Eastport, plus crab cakes, oysters and rockfish along the Annapolis harbour.
Cross the Chesapeake Bay Bridge to the Eastern Shore
The 4.3-mile bridge from Anne Arundel County to Kent Island opens up St. Michaels, Tilghman Island and Oxford, waterman villages, lighthouses and skipjack sailboats.
Discover Baltimore's Inner Harbor
A 40-minute drive from Annapolis, the National Aquarium, USS Constellation, Fort McHenry (birthplace of 'The Star-Spangled Banner') and the American Visionary Art Museum.
Step back at Historic London Town & Gardens
An 18th-century tobacco port on the South River in Edgewater, an 8-acre woodland garden, restored William Brown House and active archaeology on the lost colonial town.
Catch a race or festival in Anne Arundel County
The Annapolis Boat Shows (sail and power in October), Maryland Renaissance Festival in Crownsville, Annapolis Songwriters Festival and Fourth of July fireworks over the harbour.
Source: visitannapolis.org, the official Annapolis & Anne Arundel County destination marketing organisation.
Ready for Annapolis?
Pair a few nights on the harbour with Washington DC, Baltimore's Inner Harbor or a run across the Bay Bridge to the Eastern Shore, we'll build the hotel, the sail, the crab feast and the day trips around you.