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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
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.
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.
Options
Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
Reviews
12 reviews
Total reviews and rating from Viator & Tripadvisor
Great Time
O2425DXscottm,,Jan 26, 2026
- Review from Tripadvisor
5.00Our tour guide Ryan was awesome and he was extremely knowledgeable!! We had a blast with him and made friends with the other two people on the tour. I highly recommend this tour and can’t wait for Ryan to start a tour in Baltimore as we’ll be the first in line!!
Get the night started right!
Mark S,,Jan 20, 2026
- Review from Viator
5.00Good intro to downtown Annapolis, great bars, & learn about local spirits & tastes. Plenty of time afterwards to get a meal and continue exploring. Had a great time!!
Excellent
Dublin999,,Jan 16, 2026
- Review from Tripadvisor
5.00Really great tour! Loved the whiskey history and would highly recommend
Fantastic for Locals or Tourists!
veronicaf934,,Jan 10, 2026
- Review from Tripadvisor
5.00Ryan was a fantastic and knowledgeable host! Such a great way to spend an afternoon with friends, and perfect for locals or tourists! Ryan is very engaging, and will answer any questions you may have! Well worth the cost!
History and pub crawling!
maxp217,,Jan 7, 2026
- Review from Tripadvisor
5.00This tour was so much fun! Ryan really brought to life the history aspect with some great stories, and the pubs were all really cool and different to eachother. 10/10 way to see Annapolis, highly recommend!
Great experience, 0erfect for out of town guests!
guymI4975RB,,Dec 30, 2025
- Review from Tripadvisor
5.00This was such a fun experience! The drinks were great and the history behind everything made it so much fun. We had a group of friends visiting, and this was the perfect happy hour to show them downtown Annapolis. Would recommend to anyone (Ryan even accommodated the non drinker in our group).
So much fun!
matH4085LZ,,Dec 28, 2025
- Review from Tripadvisor
5.00Annapolis is such a quaint town I wanted to visit with friends from out of town and didn't know where to start. The tour was a bargain and took all the pressure off figuring out what to do. It launched us into a memorable evening with great friends. The new perspective on American history was a bonus!
Local Annapolis Family
bradn996,,Dec 26, 2025
- Review from Tripadvisor
5.00Excellent tour, Ryan is a very good story teller and gives great drink recommendations at every stop. Would highly recommend to do with a group of friends or family.
Awesome tour
T8962GSjf,,Dec 21, 2025
- Review from Tripadvisor
5.00Our tour with Ryan Lyles was super! His knowledge of the history of alcohol and Annapolis was impressive. He's also matched different cocktails to different historic periods which made this tour most interesting and tasty!
Very Interesting
Flyer03335911077,,Dec 6, 2025
- Review from Tripadvisor
5.00Ryan 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!!
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Operated by Tipsy Bay Co.