Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
Overview
Available languages
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
Additional Info
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
What To Expect
Colonial 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.
Options
Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
What‘s Included
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
29 reviews
Total reviews and rating from Viator & Tripadvisor
Fun time in Annapolis
Sightsee56076189512,Jun 6, 2026
- Review from Tripadvisor
5.00Ryan was great. We always like to hear interesting history in a fun way. He was very patient and adaptable to this assorted group of people.
Highly recommended
735timt,Jun 5, 2026
- Review from Tripadvisor
5.00If you like a little history while you enjoy amazing cocktails in three of the best pubs in Annapolis take this tour. Ryan is a great host, tour guide and teacher of the evolution of alcoholic drinks in Maryland.
Excellent Maryland-centric whiskey stories!
BillS1122012,May 14, 2026
- Review from Tripadvisor
5.00Okay, Ryan deserves the 5-star rating that all the previous reviews have given him. We so enjoyed his story telling, and his whiskey (really spirits in general) is so deep! Amazing! We’re already building a list of friends we want to bring along for another outing with Ryan!
Unique Way to See Annapolis
916danielley,May 9, 2026
- Review from Tripadvisor
5.00What a unique way to see the charm of Annapolis! Ryan was a very entertaining tour guide. This was a great date night. Highly recommend and we’ll be back again!
Great Annapolis Experience
Joel Y,Apr 30, 2026
- Review from Viator
5.00It is a lot of fun and very informative. The beverages were all excellent. The bars/restaurants we went to I would go to again. I was looking for a fun date night with my wife and this absolutely delivered.
Educational and fun
Roving575546,Apr 27, 2026
- Review from Tripadvisor
5.00Very fun and informative. Excellent couples evening. We really enjoyed ourselves.
Highly Recommend!
TracySeiger,Apr 25, 2026
- Review from Tripadvisor
5.00Highly recommend this tour! Fun, knowledgable, and loved the bars and suggested drinks. Great time!
Great tour!!!
Elizabeth M,Apr 11, 2026
- Review from Viator
5.00Really fun and informative. Best history/entertaining tour I've been on. Learned so much and the drinks were great too!!!
Great Experience
Michelle J,Apr 1, 2026
- Review from Tripadvisor
5.00My husband and I booked Ryan’s tour during a two night trip to Annapolis over my spring break. What a great way to kick off our visit! Ryan shared fun stories about the history of whiskey in MD and was just an overall great guy to have a drink with. He was personable, shared other recommendations, and we loved learning historical facts from three different time periods…all accompanied by a recommended drink. This is an absolute must tour if you’re visiting Annapolis. Book now before he raises his prices!
Great tour
Kate W,Mar 28, 2026
- Review from Viator
5.00We had a great time on this tour. The guide had interesting stories and great drink recommendations.
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Operated by Tipsy Bay Co.