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2 hours
Mobile ticket
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. Perfect for whiskey enthusiasts and history buffs alike, this tour offers a relaxed atmosphere to toast the past and enjoy the present. Dress comfortably as you stroll through downtown, rain or shine, and prepare for a fun evening immersed in tipsy history.
- 2-hour historical pub crawl through downtown Annapolis
- Discover how drinking shaped Annapolis' history
- Enjoy recommended drinks at each stop, not included in the price
- Limited walking involved; dress for comfort and the weather
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
For a full refund, cancel at least 24 hours before the scheduled departure time.
Annapolis Historic District
Come raise a glass with us on a historical pub crawl that shares the untold stories of how drinking shaped Annapolis, Maryland, and the nation itself. At each stop, we’ll dive into a different era— paired with a recommended drink that was the rage at the time. We will dive into the colonial rum obsession, Maryland’s rich whiskey distilling roots, and the bold few who treated Prohibition like a suggestion, not a law. We will roughly be at each pub for 30 minutes and will pass by some of Annapolis' most iconic places like the State House, Ego Alley and Main Street. Join us to toast the past, enjoy the present, and experience history with a tipsy twist.
A guided drinking history tour at iconic Pubs in Annapolis
Although we have recommended drinks at each stop they are not included with the price of the tour. This allows our guests to enjoy alcohol at their own pace and responsibly.
3 reviews
Total reviews and rating from Viator & Tripadvisor
Flyer03335911077,,Dec 6, 2025
- Review from Tripadvisor
Ryan was a great tour guide! He was very knowledgeable about history and alcohol's impact. He also gave us tips on local places to try. I would highly recommend taking his tour!!
L3769TVjaimej,,Nov 21, 2025
- Review from Tripadvisor
I had a great time on this whiskey tour in Annapolis! It was the perfect mix of fun with relaxing vibes, and really interesting information about the history of whiskey and vodka in Annapolis. The guide was super knowledgeable and friendly, and the tasting experience was great and having it be in local restaurants that I frequent made it even better. I highly recommend for anyone looking for a unique and cool outing!
H1141MYalexs,,Oct 24, 2025
- Review from Tripadvisor
I had a great time with Ryan during our tour! He's a great storyteller and I learned a lot during our time. The paired cocktails were delicious and we had a great time.
Operated by Tipsy Bay Co.