Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Explore thousands of experiences from activities and attractions to day tours and transfer.

Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities.

Members get extra discounts on thousands of experiences and hotels. Sign up today.


Explore the world from home

Top Activities in Annapolis

See all 319 things to do in Annapolis

Map

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

Annapolis is a fantastic place for a family escape. Bring the youngsters along and enjoy these family friendly experiences together:

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.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

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.

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

Unusual Spring Break Destinations for Families

Take your kids to discover somewhere new with these 6 unusual spring break destinations for families.

Camille Meyers
Unusual Spring Break Destinations for Families. Opens in a new window.

Guide to the DC Cherry Blossom Festival

Celebrating the blooming blossoms in the nation’s capital

Chloe Mulliner
Guide to the DC Cherry Blossom Festival. Opens in a new window.

Best College Towns to Spend Winter Break In

Discover the best college towns to spend winter break in, whether you want to hit the slopes or explore Christmas markets.

Expedia
Best College Towns to Spend Winter Break In. Opens in a new window.

Monuments, Memorials, & Museums to Visit This Veterans Day

Take some time at the monuments, memorials, and museums across the United States of America to honor those who’ve served on a Veterans Day vacation.

Camille Meyers
Monuments, Memorials, & Museums to Visit This Veterans Day. Opens in a new window.

Top Museums in Washington D.C.

Discover the best science, history, and art museums in Washington D.C. to plan a fun-filled trip.

Expedia
Top Museums in Washington D.C.. Opens in a new window.

America’s Favorite Cheap Places to Eat

Savoring America’s melting pot of cheap eats and unique treats

Jennifer Cuellar
America’s Favorite Cheap Places to Eat. Opens in a new window.

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?

Put these attractions high on your to-do list to get the most out of your visit:

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

What can you do in Annapolis for free?

You'll barely have time to dig your wallet out of your backpack with so many free attractions:

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