Top 10 cultural & heritage things to do in Annapolis

1. Historic ghost stories walking tour of Annapolis

Two hours on foot, relaxed pace — explore colonial history and ghost stories with a focus on local legends and documented events.

2. Outdoor watercolor painting class in Annapolis

Two 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.

3. Interactive walking scavenger hunt in Annapolis

Flexible self-guided walking tour—explore historic stories, solve riddles, and enjoy architecture throughout Annapolis at your own pace using a mobile app.

4. Private cultural walking tour of historic Annapolis

Two hours of flat walking — explore historic Annapolis waterfront with a focus on culture and storytelling from local history.

5. Historic walking tour of Annapolis' harbor and colonial downtown

Two-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

6. Historical pub crawl in Annapolis

Two-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

7. Outdoor painting class in Annapolis with a local artist

Two 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

8. Colonial and maritime history walking tour of Annapolis

Two 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

9. Urban sketching and painting class in Annapolis

Three-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

10. Historic pub crawl in Annapolis: tales of scandal and intrigue

Two 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