ITINERARIES

There is a lot to see and do in this beautiful seaside town, the question is, what are you looking to experience? Select a category below to discover more about Annapolis.

History in Annapolis
History in Annapolis

Annapolis is nothing if not historic. Transformative historical icons such as Jefferson, Franklin, and Washington have wandered Annapolis’ brick streets,......

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The Chesapeake Experience
The Chesapeake Experience

Experiencing the Chesapeake is all about getting your feet wet, tasting its flavors, and learning about its history. ...

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Walkable Downtown
Walkable Downtown

Annapolis is consistently ranked one of America’s most walkable towns for good reason......

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Family Friendly
Family Friendly

Looking for something to do with the whole family? We've got you covered. Bring the dog along, too! Annapolis has a ton of things to choose from to......

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Art in Annapolis
Art in Annapolis

Consistently ranked as one of the country's top 25 arts destinations, Annapolis is home to over a dozen art galleries and studios....

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Girls Weekend
Girls Weekend

We all need a getaway once and awhile. So, grab the girls and head to Annapolis for the weekend. Filled with shopping and dining options, fun activities......

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Adventure in Annapolis
Adventure in Annapolis

Seeking a little adventure while visiting Annapolis? We have you covered. From adventures out on the Chesapeake Bay to high-flying, adrenaline-filled......

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Annapolis Countryside
Annapolis Countryside

Cross over the South River Bridge from downtown Annapolis and, almost immediately, things start to feel different. The traffic dwindles, the pace slows,......

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Annapolis, Baltimore, DC Weekend
Annapolis, Baltimore, DC Weekend

In addition to experiencing Annapolis and the Chesapeake, add nearby Baltimore and Washington D.C. to your itinerary to visit a trio of cities rich in history and culture....

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