Tipsy History Tour: 300+ Years of Annapolis Drinking History

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

Itinerary

1. Colonial Annapolis Historic District · 120 min

   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.

Meeting point

Everyone meets at the meeting point.

Good to know

• 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.

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