What to do in Annapolis, MD

Activities, attractions and tours

Annapolis
Annapolis
U.S. Naval Academy featuring military items, interior views and heritage architecture
Annapolis as well as a couple
Annapolis

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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What to do in Annapolis


Popular places to visit

Explore areas of Annapolis

Beautiful troll downtown Annapolis...
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Historic District

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Historic District
Aerial view of colorful sailboat moorings and docks on Spa Creek, in historic downtown Annapolis Maryland on a fall day

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

Eastport
Aerial Panoramic View Annapolis Maryland State House Capital City

Murray Hill

If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.

Murray Hill
Been a fan of this house since a youngin'. The tree draped driveway has always been a good look about this time of year.

Arundel on the Bay

If you're spending some time in Arundel on the Bay, Northern Chesapeake Bay and Chesapeake Bay are top sights worth seeing.

Arundel on the Bay
Beach chairs by Chesapeake Bay at Robert Morris Inn, Oxford, Maryland

Hillsmere

While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.

Hillsmere
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Cape Saint Claire

While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.

Cape Saint Claire

 

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Frequently asked questions

Is Annapolis worth visiting?
One of the most common things to do in Annapolis is visit Annapolis City Dock. Check this major sight off your itinerary, then discover more of this area's watersports and history.
How do I spend a day in Annapolis?
After you've visited leading attractions like Annapolis City Dock and Sandy Point Beach, spend some time discovering Annapolis's retail and dining scene.
What is the top tourist attraction in Annapolis?
You can't go home without exploring Annapolis City Dock, rated the top tourist attraction in Annapolis.
Is three days enough to stay in Annapolis?
Three days will give you enough time to tick off popular city sights, such as Annapolis City Dock, Sandy Point Beach and London Town. The average stay in Annapolis is two days. If you have the urge to extend your getaway, Washington isn't far away.
Is Annapolis a walkable city?
Some major attractions in Annapolis, including Annapolis City Dock and Bay Ridge Beach, are within walking distance. You can also experience several of the city's popular neighbourhoods on foot. Just 5 kms (3 miles) from the city centre of Annapolis is Parole and Historic District is 0.16 kms (0.10 miles) away.
What are some activities to do in Annapolis with kids?
Whether you're holidaying with hard-to-please teens or tiny adventurers, a fun-filled itinerary takes your trip to the next level. Take a look at our ideas for what to do in Annapolis with kids.

What to do in Annapolis for adults?
Whether you're a culture enthusiast, avid foodie or outdoor explorer, there are lots of things to do in Annapolis for adults including 14 Fleet Street and U.S. Naval Academy.
Are there free things to do in Annapolis?
In Annapolis, Annapolis City Dock is a top spot for anyone looking to tour the city without reaching for their wallet. Also, wander around the local parks and neighbourhoods, and ask for ideas from a local tour guide. It's a simple way to explore the best free things to do in Annapolis.