Tipsy History Tour: 300+ Years of Annapolis Drinking History

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Tipsy History Tour: 300+ Years of Annapolis Drinking History

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 US$41  per guest
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Adult x1
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Instant Confirmation
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Earliest available date: September 13, 2026
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
2 hours
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Number of Guests
1 - 15 guests
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Language
English
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Other
Vegetarian, Pet-friendly
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Digital Ticket
Mobile or paper ticket accepted

Dive into Annapolis' boozy past on a 2-hour pub crawl. Enjoy a unique blend of history and drinks. Explore, sip, and learn how the local drinking culture shaped the city and beyond.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

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

What You Get

A guided drinking history tour at iconic Pubs in Annapolis
Alcoholic beverages
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.

Good To Know

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Service animals allowed

What You’ll Experience

1

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.
2 hoursAdmission Ticket Free

Meeting & Pickup

Meeting Point

Galway Bay Irish Restaurant and Pub, Maryland Avenue, Anne Arundel County Maryland, United States, US, 21401

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See the hostess at Galway Bay and let them know you are with us.
End Point

DRY 85, Main Street, Anne Arundel County Maryland, United States, US, 21401

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Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund.

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Reviews
5.0
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based on 47 reviews
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(TripAdvisor)
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Entertaining and so Fun!!
August 31, 2026

Ryan was so delightful!! He was funny and knowledgeable and told the stories in such an engaging way - not to mention he handled our sometimes rowdy group with such grace and really rolled with the...read more

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(Viator)
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My girlfriend and I had...
August 29, 2026

My girlfriend and I had an amazing time on the Tipsy History Tour! Our tour guide was incredibly knowledgeable and did a great job making the history interesting, entertaining, and fun. We learned ...read more

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(TripAdvisor)
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Amazing experience
August 21, 2026

Fantastic tour. This was a great experience and well worth the money. Highly recommend

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(TripAdvisor)
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A Walking Happy Hour
August 19, 2026

Ryan’s tour is the best. A unique historical perspective on the Town of Annapolis from a drinking perspective. An important part of American History. It’s a great walking happy hour. Don’t miss it!

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(Viator)
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This was a fun experience...
August 12, 2026

This was a fun experience with all sorts of rid bits about history about the area and the drinks we enjoyed. The guide was entertaining and very knowledgeable!

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