What to do in Annapolis, MD

Activities, attractions and tours

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.

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Most fun & popular experiences in Annapolis

What to do in Annapolis

Free Things to Do in Annapolis

Some say the best things in life are free. Be sure to visit the following around Annapolis:

Annapolis Maritime Museum - Packed with exhibits and artifacts, this place is a paradise for inquiring minds.

St John's College - Be wowed by the creativity and design of this impressive example of modernistic architecture.

Thurgood Marshall Memorial - Come to grips with some of the historical background of the area through this attraction.

Ego Alley - Wander down the streets and immerse yourself in the charm and character of this lively local hangout.

Annapolis City Dock - Look up your guidebook and discover why this place deserves a spot on your itinerary.

Helen Avalynne Tawes Garden - Refresh your mind, body and soul by spending some time with Mother Nature.

Things to Do in Annapolis with Kids

There's fun for the whole family no matter where you go in Annapolis. Here are some family friendly experiences you can do together that are bound to make your vacation a blast:


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Frequently asked questions

What to do in Annapolis on a sunny day?
What to do in Annapolis on a rainy day?
What should I not miss in Annapolis?
Don’t go home without checking off the following list of incredible sights:

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

Are there cheap things to do in Annapolis?
What can you do in Annapolis for free?
You could even leave your cash in the hotel safe for the day, because these attractions won’t cost you a dime:

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

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