Top 19 things to do in Annapolis
Sorted by traveller rating
011. Historic ghost stories walking tour of Annapolis
2 hoursFrom₹46,717/ personInstant confirmationTwo hours on foot, relaxed pace — explore colonial history and ghost stories with a focus on local legends and documented events.
022. Outdoor watercolor painting class in Annapolis
1.5 hoursFrom₹9,306/ personFree cancellationTwo hours of outdoor painting instruction — learn watercolor techniques while capturing iconic sailboats in the historic district of Annapolis, led by an award-winning local artist.
033. Interactive walking scavenger hunt in Annapolis
2 hoursFrom₹3,428/ personFree cancellationInstant confirmationFlexible self-guided walking tour—explore historic stories, solve riddles, and enjoy architecture throughout Annapolis at your own pace using a mobile app.
044. Private cultural walking tour of historic Annapolis
2 hoursFrom₹56,720/ personFree cancellationInstant confirmationTwo hours of flat walking — explore historic Annapolis waterfront with a focus on culture and storytelling from local history.
055. Historic walking tour of Annapolis' harbor and colonial downtown
5.0· 42 reviews1.8 hoursFrom₹23,021/ personFree cancellationTwo-hour walking tour covering Annapolis' harbor, Georgian mansions, and the Maryland State House, led by an engaging guide with personal stories.
“My wife and I arranged a private walking tour with Michael, which turned out to be the best part of our visit to Annapolis. The outstanding reviews are accurate! His tour of the Naval Academy and historic downtown was a wonderful mix of history, interesting facts, and enjoyment. Michael is an excellent guide, and we strongly suggest him to anyone coming to Annapolis for the first time.”— Q7841VKjamesw
066. Historical pub crawl in Annapolis
5.0· 26 reviews2 hoursFrom₹2,939/ personFree cancellationInstant confirmationTwo-hour walking tour through downtown Annapolis — explore historical tales paired with drinks at each location, offering insights into the city’s past.
“I strongly recommend this tour! It was enjoyable and informative, and I really appreciated the choice of bars and drink recommendations. I had a fantastic time.”— TracySeiger
077. Outdoor painting class in Annapolis with a local artist
5.0· 7 reviews1.5 hoursFrom₹9,306/ personFree cancellationTwo hours of outdoor painting in the historic district of Annapolis, led by an award-winning watercolorist.
“This is an excellent opportunity to immerse yourself in the charm of Annapolis' old town, appreciating its architecture and history while exploring sketching and watercolors. The teacher is very patient and tailored their approach to each student's skill level. Inspiring and engaging — truly a must-do.”— Blanche_M
088. Colonial and maritime history walking tour of Annapolis
5.0· 1 reviews2 hoursFrom₹3,821/ personFree cancellationInstant confirmationTwo hours on foot — explore Annapolis' Historic District, visit key landmarks, and learn about colonial life from an expert guide.
“I highly recommend this walking tour. It was easy-paced with frequent stops. Our guide, William, shared a wealth of knowledge and was very engaging. I learned far more than I expected.”— LaurieAnne_J
099. Urban sketching and painting class in Annapolis
5.0· 1 reviews1.5 hoursFrom₹9,306/ personFree cancellationThree-hour outdoor painting session — learn from an award-winning local artist while capturing the architecture of Annapolis' historic district.
“I had a fantastic time. Em was an excellent instructor who made me feel at ease despite my lack of art experience. She was also very engaging in conversation. I highly recommend this activity.”— Sam_E
1010. Historic pub crawl in Annapolis: tales of scandal and intrigue
5.0· 1 reviews2 hoursFrom₹2,939/ personFree cancellationInstant confirmationTwo hours of bar-hopping (approx. 0.5 miles) — visit three local taverns while hearing stories of Annapolis' scandalous past and colorful history, adults only.
“Baltimore Tours and Crawls originated in Annapolis, so their expertise is evident. They provide a variety of engaging tours in the Fells Point area, including the Walking Ghost Tour, Haunted Pub Crawl, Twisted History Tour, Bootleggers & Rum Runners Tour, and the Sports Legends Tour. Each tour caters to different interests—historical, supernatural, athletic, and quirky stories. Departing from the historic Admiral Fells Inn around 8 PM, these tours last about 90 minutes. The Pub Crawl is particularly enjoyable if you’re not driving. The guides are highly knowledgeable and entertaining, having earned the title of "Best Downtown Tour" in Fells Point for three consecutive years. Dogs are welcome as long as they are leashed and friendly.”— Steve C
1111. Historic Annapolis walking tour with a small group
4.8· 11 reviewsFrom₹3,429/ personFree cancellationInstant confirmationTwo hours, 2 miles of walking through Annapolis — guided small group setting at a relaxed pace, rain or shine, with frequent stops.
“As a resident, I'm familiar with much of what was shared, yet I still discover new aspects of my hometown on tours like this. My friend visiting from out of town, who had never experienced Annapolis before, also found the tour enjoyable. Our guide, Rebecca, mentioned she was a local, but both she and her partner frequently mispronounced Roger Taney's name; Marylanders pronounce it as "tawney." It wasn't a major issue, but it did make me curious.”— fiedhp
1212. Historic Annapolis food tour
4.7· 46 reviews3.5 hoursFrom₹7,837/ personFree cancellationThree-and-a-half hours walking through downtown Annapolis with tastings from local restaurants at historic sites.
“This tour was fantastic, with delicious food and wonderful company. Our guide was friendly and well-informed, sharing plenty of interesting historical insights.”— Pat_M
