Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Overview

Available languages

English

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‘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.

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.

2 hours • Admission Not Applicable

Options

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Reviews

5.00

1 review

Total reviews and rating from Viator & Tripadvisor

Fantastic time on this boozy history tour
H1141MYalexs,
Oct 24, 2025
- Review from Tripadvisor
5.00
I had a great time with Ryan during our tour! He's a great storyteller and I learned a lot during our time. The paired cocktails were delicious and we had a great time.