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 and Anne Arundel County.

Walkable Downtown

Annapolis is consistently ranked one of America’s most walkable towns for good reason. This quaint, historic, waterfront town has changed little since its inception in the mid-17th century. 

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Annapolis, Baltimore, DC Weekend

Why not cross off three great cities while visiting Annapolis? A short drive away, Baltimore, Annapolis, and Washington D.C. offer a great, three-day travel experience. Fly into BWI Thurgood Marshall Airport from anywhere in the country, and...

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Girls Weekend

We all need a getaway once and a while. So, grab the girls and head to Annapolis for the weekend. Filled with shopping and dining options, fun activities and a great nightlife, Annapolis is the perfect place to get away with your gal pals for...

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Annapolis Countryside

You think you know Annapolis, but have you experienced the Countryside? From bayside harbours to historic artifacts and landmarks, the Annapolis Countryside has many hidden gems for friends and families alike to enjoy.

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The Chesapeake Experience

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.

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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 activities and tours, there's something to take care of your thrill-seeking needs. 

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Art In Annapolis

Enjoy exploring art in new cities? Then Annapolis is for you. Consistently ranked as one of the country's top 25 arts destinations, Annapolis is home to over 20 art galleries, along with performing arts studios and live music venues.

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Family Friendly

Family time is precious. There never seems to be enough of it! So, when you get together with loved ones, you want it to be special. Whether you’re traveling with toddlers, teenagers or ‘tweens, you can’t go wrong with...

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History In Annapolis

Are you a history buff? If so, you’ve come to the right place! As our nation’s first peacetime capital, you could say our nation took its first breath in Annapolis when the Treaty of Paris was ratified here – officially...

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