Annapolis is nothing if not historic. Transformative historical icons such as Jefferson, Franklin, and Washington have wandered Annapolis' brick streets, frequenting many of the still-standing taverns and buildings in town.

Home to the county's oldest state house in continuous use (once the U.S.'s capitol building), Annapolis boasts a rich legacy dating back to America's inception. Streets lined with 18th-century homes, historic buildings-turned-museums, and centuries-old taverns and pubs make Annapolis a history buff's paradise. Lean on our three-day itinerary for a robust, historical trip to Annapolis:

Day One 

Arrive in the afternoon and hit the streets, getting to know Annapolis. Stop by our Visitors Center (26 West St, Annapolis, MD 21401) to learn about events and things to do before hitting the streets. Check into your hotel or historic B&B before joining a tour by brick-lined streets or Bay for a fascinating history lesson. Close out the day with dinner at a historic building on City Dock or State Circle/Maryland Avenue.

William Paca House and Gardens

Day Two

Enjoy brunch or breakfast before checking out Historic Annapolis, a foundation that oversees some of the city's oldest and most historic sites. Stop by the United States Naval Academy (two valid forms of ID required), where you can take a guided tour of this impressive institution, and leave time to poke around the world-class USNA Museum for an education on our Navy's storied history. Dine at the "Yard" at Drydock Restaurant or The Alley before wandering back down historic Maryland Avenue for a quick tour through the Maryland State House. Join a guided history tour or a water tour watching the sun set before stopping for dinner at Reynolds or Middleton's Tavern, well-known hangouts of our founding fathers.

Day Three

Historic London Towne and Gardens

After breakfast, head out early for Historic London Town and Gardens and a drive through the Annapolis Countryside, checking out the historic areas dotting the south of Anne Arundel County. Stop for lunch at a seafood restaurant for a traditional taste of the Chesapeake Bay before heading home.