Immerse yourself in the colonial charm of the Annapolis Historic District, where cobblestone streets and stunning maritime architecture tell stories of American history. Discover top-rated walking tours, lively pub crawls, and expert-led cultural excursions that bring the past to life. Whether you are exploring legendary landmarks or enjoying a local tasting experience, our curated activities offer the perfect way to experience Maryland's breathtaking heritage. Book your unforgettable Annapolis adventure today and uncover the hidden gems of this historic seaside treasure!
$30–$462 typical
Median price is $35, with a wide range up to $1,476
4.73★ average
Based on 38 pooled reviews with ~100% positive sentiment
2–4.1 hours typical
Median duration is 2 hours
History & Pub Crawls
100% of tours are historical, 75% are pub crawls
75% free cancellation
75% of options also offer instant confirmation
Knowledgeable guides
Reviewers highlight interesting and great tasting experiences
10 Products
Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended drinks at each stop. From rebels to rum-runners, each location reveals fascinating stories paired with a drink that defines the era...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Pull up a bar stool and lean into tales of murder, debauchery, and gruesome tragedies on this dramatic haunted pub crawl of the Annapolis historic district.
Discover the haunted history of Annapolis on a captivating evening ghost tour. Travelers wander through narrow streets alongside a knowledgeable guide dressed in period attire while hearing tales of supernatural occurrences and unexplained phenomena. This family-friendly walk explores haunted sites ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
The Hidden History Pub Crawl is a tour through Annapolis' scandalous past. Sip on a beverage while entertained by stories of historical conspiracies, murder, riots and forgotten tales as your guide brings to life the city’s juiciest stories. With different stories every night, this is the most intri...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Stroll through Annapolis’ storied streets and visit iconic landmarks. Pause for a hearty lunch or dinner at a local favorite, Galway Bay Restaurant.
Discover the quirky tales and unusual stories of Annapolis on this engaging walking tour. Led by a colonial-attired guide, explore fascinating anecdotes including the Russian sailor's grave in the Annapolis National Cemetery and the Confederate captain who never conceded defeat. Perfect for those cu...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a knowledgeable colonial-costumed expert, wander through the historic district and delve into the city's 18th-century Golden Age. Stand in the M...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Discover the profound legacy of African American history in Maryland on an enlightening two-hour walking tour in Annapolis. Starting near Market House Park, journey through time to encounter significant landmarks such as the Alex Haley statue and the Maryland State House while learning about the vit...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Explore the eerie side of Annapolis with the Spirits & Spirits tour, blending a captivating walking tour through the Historic District with a thrilling cruise on the haunted waterways. Listen to spooky stories from your Ghost Guide, uncover nautical myths, and indulge in beverages available for purc...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover the history and heritage of the Maryland State House, the oldest continuously operating state capitol in the United States, where pivotal mom...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Landmarks travelers visit on the same route as Annapolis Historic District.