Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Top things to do in Annapolis

See all 168 things to do in Annapolis

Things To Do In Annapolis

Constantly in search of an enlightening experience and unique ways to get your kicks, you're prepared to check out a new destination like a pro. You're keen to chart a course in a new direction. It's not difficult to fill an itinerary, because Expedia Canada makes it a breeze to book tons of things to do. Book your activities now, and the only thing you'll have left to do is pack your suitcase and prepare to have fun. Coming up: Annapolis!

  • Book your favourite activities and day trips on Expedia Canada for a great price, and you'll still have money for a dream hotel or fine meal while you're visiting. The things to do in Annapolis are not only topnotch, but they won't bust your budget. We have 168 things to do here, and you can reserve them starting at just C$10 .
  • Annapolis is popular among sightseers like you. In fact, many travellers have been visiting Annapolis to get a taste of local culture and explore the best things to do, and most are already planning to come back. The most booked things to do can earn the enthusiasm of even experienced globetrotters, and it's easy to see why. Our collection includes a wide range of historically themed excursions and opportunities for excitement. With unique ways to check out the best this area has to provide like a Small-Group Original Annapolis Seafood Crawl, there is a huge selection of things to do to choose from when you browse the top-quality day trips here at Expedia Canada.

Our activities are the perfect way to organize your getaway. You'll need a game plan to make the most of a trip to Annapolis, particularly when you long to include outdoor activities and trips to museums. And it's a no-brainer that you don't plan to sleep all day—you're ready to get out and see what life is like for locals. You're eager to sign up for the best activities around, and an afternoon walking through charming neighbourhoods is a perfect way to spend an afternoon. Book group tours on Expedia Canada, and you'll learn all about the city's history along the way.

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.