Fun Things To Do

Looking for fun things to do in Annapolis?

Your wish is our command.

Historic Annapolis is rich with events, attractions, and other cool things to do, regardless of who you are.

Here at the O’Callaghan Hotel, we know what it takes to make our guests happy. That’s why we put together this handy visitor’s guide to help you find things that you’ll enjoy seeing and doing while you spend time in our wonderful city.

Take a look at some of the things that we’ve listed here. We’re sure you’ll find fun things to do in Annapolis that will help make your visit a memorable one.

Tours and Activities to Educate and Entertain

• Do you want to see the city on foot?Then Walking Tours of Annapolis is for you! Walk the cobbled streets of the city with costumed colonial guides who share local history and folklore in an engaging, informative and compelling tour that you won’t soon forget.
• Would you prefer to see Annapolis from the water?Then consider Schooner Woodwind Public Cruises. Explore the reason why Annapolis is often considered to be “America’s Sailing Capital”. You can either help raise the sails or elect to sit back and take in the sights of the Chesapeake Bay as the waters carry you past the Naval Academy and other local landmarks.
• Would you like to see where the Maryland General Assembly Convenes?Then take a tour of the Maryland State House. Here, you’ll see the oldest state capitol in continuous legislative use and this fun, informative tour will teach you the history behind the building.
• Would you like to see where future military officers train?Then go visit the United States Naval Academy Visitor Center and Tour. You’ll be able to tour the grounds of the US Naval Academy, where future officers of the US Navy and US Marine Corps train for their service.
• Perhaps you’d like to take a tour of the city in a new and exciting way?Then the Downtown Segway Tour is for you! Any Annapolis tourist should get a kick out of this novel approach to seeing some of the city’s most popular sites.
• Do you want something that will keep the kids entertained?Take them on a Pirate Cruise! On this adventure, the little ones will be able to join a pirate crew, work together to find buried treasure and walk away with new stories to tell!