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Annapolis Tours,
Attractions & Experiences 

When visiting Annapolis, it is fun to have a professional guided walking tour, tour by trolley, electric cart, or boat.  Annapolis tour guides will make learning about Annapolis a fun experience. The top guided tours in Annapolis, Maryland, all start in the downtown area. Check in with the tour companies listed below and to get tour tickets.They focus on history, Chesapeake Bay, the United States Naval Academy, ghost stories, and specialty themes, including historical themes, ghosts, haunted history tours, colonial history, African American history, and scandalous, weird, and wacky tours. If you prefer self guided walking tour click here for a tour by the National Park Service. Use the links below to book your guided tour in downtown Annapolis.

Annapolis is filled with attractions you will enjoy. During the day, check out the museums, historic home tours, shop the boutiques, take a cruise on the bay, or grab a table at a cafe and enjoy people watching. In the evening, check out the concert and performing art venues, escape rooms, local bands playing in the pubs, or a cultural event at one of the local theatres or performing art venues. Contact venues listed below to get tickets.

While the City Dock is under construction, some of our favorite places to be along the waterfront are the view from the second floor of the USNA Visitors Center, the street-end park on Prince George Street, walking along the US Naval Academy along Spa Creek and the Severn River, and the Eastport Bridge. Of course, being on the water is fun as well, plan time to get out on the water while you are here.

The Best Annapolis Tours, Attractions and Experiences

 

The businesses in bold financially support the Downtown Annapolis Partnership
a 501 (c) (3) non-profit working to make downtown Annapolis even better.

Colonial tours in downtown Annapolis

Annapolis Tour Operators

Schooner Woodwind Sailing Cruises 

Annapolis sailing cruises

Tickets

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Naval Academy Visitors Center 

tours of USNA and gift shop

Tickets

Watermark 

Annapolis tours, charters & cruises

Tickets       

Annapolis Eventours

Annapolis Ghost Tours

Colonial Tours of Annapolis

Pirate Adventures on the Chesapeake

Annapolis Museums, Performing Arts Groups & Attractions

Annapolis Boat Shows

spring and fall boat shows

Tickets 

 

Annapolis Summer Garden Theatre

outdoor community theatre

Tickets

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Annapolis Symphony Orchestra 

performing arts organization

Tickets

Elizabeth Myers Mitchell Art Museum 

St. John's College art museum

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Hammond-Harwood House

historic mansion and museum

Historic Annapolis, Inc. 

Museum of Historic Annapolis, William Paca House, Hogshead

Tickets

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Maryland Hall 

performing and visual arts and education center

Tickets

Mission Escape Rooms 

interactive escape room experience 

Tickets

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​United States Naval Academy Museum

museum that tells the story of people who have served their country at sea

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Annapolis Maritime Museum

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Banneker Douglas Tubman Museum

Charles Carroll House

Chesapeake Children's Museum

Chesapeake Crossroads Heritage Area

​The Colonial Players of Annapolis

Maryland State House

Old Treasury Building

Rams Head OnStage

Check out these videos from past visitors to Annapolis
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© 2026 The Downtown Annapolis Partnership

501 (c) (3) nonprofit with a Gold-level rating on Candid. 

PO Box 6351, Annapolis, MD 21401

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