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Top things to do in Annapolis

See all 91 things to do in Annapolis

Things To Do In Annapolis

Coming up: Annapolis! You're about to point your compass in a new direction. Never one to shy away from innovative ways to get your kicks and have an enlightening experience, you're eager to check out a new locale like a pro. Book your activities now, and the only thing you'll have left to do is pack your bags and start daydreaming, because Expedia can connect you with tons of things to do.

  • Book your favorite excursion on Expedia for significant savings, and you'll still have money for a top hotel or decadent dinner while you're in town. The activities in Annapolis are not only topnotch, but they won't break the bank. We have 91 things to do here, and you can reserve them starting at just $13.
  • Annapolis is popular among travelers similar to you. In fact, many travelers have been visiting to learn about local history and participate in the best activities, and most are already planning to return. The most booked things to do can earn the curiosity of even experienced travelers, and that includes savvy visitors like you. Our list includes a wide variety of culturally themed outings and excitement. With unequaled ways to explore the best this area has to offer like a Small-Group Original Annapolis Seafood Crawl, there is an abundance of opportunities at your fingertips when you browse through all the things you can do here at Expedia.

Our activities are the perfect way to organize your trip. It takes a game plan to make the most of a trip to Annapolis, especially when you intend to include trips to museums and outdoor activities. And it's clear that you don't want to hunker down in your hotel room—you're excited to get out and see what life is like for locals. You look forward to covering the best activities around, and an exploration of historic city neighborhoods is always time well spent. Book professional regional tours on Expedia, and leave your map behind.

Things To Do in Annapolis

If you are looking for a vacation option among the historical cities of America's eastern shores, you should consider a sojourn in Annapolis. Known as the country's "Sailing Capital," things to do in Annapolis include attending the Wednesday night sailing races that take place on a regular basis on Chesapeake Bay from the end of April through August.

You can see the races best by going to Annapolis Harbor and grabbing a dockside chair.

If you enjoy the water, Annapolis excursions you might enjoy include day cruises on the bay as well as renting sailboats on the docks. If you are a Renaissance Fair aficionado, the Maryland Renaissance Fair begins in late August and continues through October. Other attractions in Annapolis include the Maryland State House, which was built in 1772 and played a significant part in the early beginnings of the United States. The United States Naval Academy is located along the shores of the Chesapeake Bay and is among the favorite choices of the average tourist for Annapolis tours. One of the must see places in the Naval Academy is Preble Hall, which houses the Academy's museum.

Because the Chesapeake Bay region of MD is renowned for its seafood, you won't want to miss the spots that specialize in the preparations of the bay's regional cuisine. The top places to eat are likely to be local restaurants a little off the beaten path. It is recommended you get a map of the city and look for side streets close to Chesapeake Bay's main harbor. However, if you love classic, picturesque Americana, you can't beat Main Street in downtown Annapolis. Its brick buildings, tall-steepled churches and old-fashioned lamp posts will make you think that you have gone back to another time.

For more information on Annapolis activities as well as the latest news on lodging and dining, contact our offices here at Expedia. Whether you are seeking art and culture, heritage tours or outdoor water-based fun, we can help you put together the Chesapeake Bay vacation of your dreams.