Tipsy History Tour: 300+ Years of Annapolis Drinking History

5.0 (51 reviews) 2 hours Free cancellation

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51 reviews

5.0

Tipsy History Tour: 300+ Years of Annapolis Drinking History — Photos: the activity supplier, via Viator

Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 2 — Photos: the activity supplier, via Viator

About this activity

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

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At a glance

Duration: 2 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Up to 15 people
People per booking: 1–15
Guide: English
Operated by: Tipsy Bay Co.

Ages: Adults (21–120 years)

What is included

Included

Included: A guided drinking history tour at iconic Pubs in Annapolis

Not included

Not included: 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.

Itinerary

Colonial Annapolis Historic District

2 hours

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.