Annapolis

Known as ‘America’s Sailing Capital’, Annapolis is a picturesque seaside city with extensive colonial history, delightful waterfront attractions and a culinary scene that showcases the fresh local seafood as well as international fare. Founded less than 30 years after the Puritans landed in Massachusetts, Annapolis has significant ties to the birth of present-day America, mainly seen through the town’s beautiful architecture. Notable buildings include the 1779 Maryland State House – once the nation’s capital and the oldest state capital in continuous legislative use – as well as the 1773 Hammon-Harwood House, a Palladian villa and the beaux-arts-style United States Naval Academy. Annapolis also features the Banneker-Douglass Museum, a former tobacco storehouse during colonial times which now houses the town’s history.

Annapolis is a walkable city, so you’ll find getting around is easy to do. The city is centred around the brick-paved Main Street, a bustling hub of restaurants, pubs and shops that leads to the waterfront City Dock where you can sip a coffee while watching the harbour. State Circle and Maryland Avenue are noted for their unique boutiques and antique stores, the Arts District offers a bohemian feel, and the tranquil neighbourhood of Eastport offers some of the best crab cake spots in the city. Come summer you can even head to the beach with a short drive across the Severn River to Sandy Point State Park.