48 Hours in Annapolis: Sailing, Seafood & Chesapeake Charm

Once the nation’s seat of government, today it blends colonial landmarks, maritime heritage, and a thriving food and arts scene into a compact and captivating city break.

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Begin your visit in the Annapolis Historic District, where cobblestone streets, Georgian homes, and centuries-old churches tell the story of America’s early years. At its heart stands the Maryland State House, the oldest U.S. state capitol still in use, where George Washington resigned his commission and the Treaty of Paris was ratified in 1783.

Walk to the nearby United States Naval Academy, one of America’s most prestigious institutions. A 90-minute guided tour leads you through the Chapel, Memorial Hall, and the crypt of Revolutionary War hero John Paul Jones. By lunchtime, head to Market House or grab a seat at a café overlooking City Dock, where you can watch sailboats parade into Ego Alley.

Spend the afternoon exploring the William Paca House & Garden, a Georgian mansion restored to its 18th-century grandeur. Inside are rooms rich with history; outside, the two-acre walled garden offers shaded paths, terraces, and period plantings that transport visitors back in time.

As night falls, Annapolis comes alive in new ways. Take a ghost tour or haunted pub crawl for an atmospheric twist on history, or, if visiting in September, join the Sunsets Concert Series at the Annapolis Maritime Museum Park Campus, where food trucks, drinks, and live music accompany a Chesapeake Bay sunset.

Start the day with a walk in Quiet Waters Park, a 340-acre green space where woodland trails, art exhibits, and waterfront overlooks make for a refreshing morning. Locals jog and cycle here, while others come simply to enjoy the calm of the South River shoreline.

If your visit falls on the first Sunday of the month, head to the First Sunday Arts Festival on West Street. From late morning into the afternoon, more than 150 artists, makers, and food vendors fill the street, with live music creating a lively, festival-like atmosphere. On other weekends, check the calendar for seasonal highlights like the River Days Festival, celebrating Chesapeake Bay with boat rides, crafts, and family-friendly entertainment.

Make your way back to the waterfront to soak up more of Annapolis’ maritime character. Explore the Annapolis Maritime Museum, where exhibits dive into the ecology and traditions of the Bay, or simply enjoy the bustle of City Dock with its mix of boats, cafés, and harbour views.

Bring your trip to a close with a true Chesapeake experience: a sunset cruise on the Bay. Watching the sky shift from pink to gold while sailboats drift past is the perfect finale. Back on shore, celebrate with a seafood feast — crab cakes and oysters are local icons — at one of the city’s many dockside restaurants.

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From colonial landmarks and maritime traditions to lively festivals and fresh Chesapeake Bay seafood, Annapolis reveals layers of history and charm at every turn. The surrounding Anne Arundel County adds another dimension, with beaches, trails, and waterfront parks inviting you to slow down and explore. Just 40 minutes from both Washington, DC and Baltimore, Annapolis is easy to reach yet feels a world apart — and while 48 hours offers a memorable introduction, you’ll soon find reasons to linger longer.

Find out more at: visitannapolis.org