Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history. Here in Annapolis, the Chesapeake is on full display in all its glory.

Make the most of your Chesapeake experience with this three-day itinerary:

Day One

Arrive in the afternoon and hit the streets, getting to know Annapolis. Stop by our Visitors Information Booth located at City Dock, or our Visitor Center (26 West Street, Annapolis, MD 21401) to grab a map and learn about events and things to do. Browse our website to get an idea of the sites, destinations, and historic landmarks. Check into your hotel (or the uniquely Chesapeake Boat & Breakfast option) before sampling the famed Chesapeake flavors at one of our many seafood restaurants. Walk along the harbor checking out the boats before grabbing some ice cream and heading back for the night.

Flags Lining Main Street

Day Two

Head to the Annapolis neighborhood of Eastport for brunch before checking out the Annapolis Maritime Museum for an in-depth lesson on the Chesapeake Bay and its traditions. Have lunch back in Annapolis before getting on the water for a water tour, or, hang out at Ego Alley in Downtown, watching boats of all kinds float in and out of the harbor. Try some more Chesapeake flavor at the restaurants on City Dock before calling it a night.

Eating crabs waterfront

Day Three

After breakfast, head over to the United States Naval Academy ( two forms of valid ID required) for a lesson in naval history, wander the grounds checking out the USNA Museum and the Armel-Leftwich Visitors Center. Before heading home, visit Historic Annapolis and the many centuries-old buildings that are open to visitors, and were once home to some of the Chesapeake's most influential residents.