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Top Activities in Annapolis

See all 401 things to do in Annapolis


What to Do in Annapolis: Must See Attractions

Annapolis Attractions

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.

Things to Do in Annapolis with Kids

There are plenty of amazing experiences in Annapolis that the whole gang will get a buzz out of. Here are a few of the best family friendly experiences in the area.

Free Things to Do in Annapolis

Leave your purse in the hotel. It's easy to amuse yourself in Annapolis without spending a penny.

Annapolis Maritime Museum - Take the entire family and set out on a journey of discovery through history with one another.

St John's College - This local landmark is an unique backdrop for some selfies.

Thurgood Marshall Memorial - Take a stroll around this historic place and discover a couple of secrets from the past.

Ego Alley - This bustling area is popular with both locals and tourists.

Annapolis City Dock - Well known among local residents, this place is worth checking out.

Helen Avalynne Tawes Garden - If you relish pottering around the garden, this place will delight your inner green thumb.

Explore The Neighborhoods of Annapolis

Historic District

While visiting Historic District, you might make a stop by sights like Annapolis City Dock and Maryland State House.

Arundel on the Bay

If you're looking for some top things to see and do in Arundel on the Bay and surrounding area, you can visit Annapolis City Dock and Maryland Quiet Waters Park.

West Annapolis

When in West Annapolis, you can plan a visit to Annapolis City Dock and Navy-Marine Corps Memorial Stadium, some noteworthy sights in the nearby area.


While there might not be top attractions in Hillsmere, you can explore the larger area and discover places like Maryland Quiet Waters Park and Annapolis City Dock.

Oyster Harbor

If you're looking for some top things to see and do in Oyster Harbor and surrounding area, you can visit Maryland Quiet Waters Park and Annapolis City Dock.

Learn More About Annapolis | Blog

Frequently Asked Questions

What to do in Annapolis on a sunny day?

What to do in Annapolis on a rainy day?

If it's raining during your visit, put your umbrella aside and dive into a couple of these fun indoor activities:

What should I not miss in Annapolis?

You just can't go home without checking off the following list of wonderful attractions:

  • U.S. Naval Academy
  • Six Flags America
  • Maryland State House
  • William Paca House

Are there cheap things to do in Annapolis?

If you're vacationing on a smaller budget, you may like to add these cheap experiences to your itinerary:

What can you do in Annapolis for free?

You could even leave your cash in the hotel safe for the day, because these terrific attractions won't cost you a cent:

  • Maryland State House
  • Annapolis City Dock
  • Westfield Annapolis Mall
  • Bowie State University