Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

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Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

(36)

Add to Wishlist

Show all photos

US$30.98 per guest

Adult x1

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Available Tomorrow

Free cancellation (24 hours notice)

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

Summary

Experience Details

What You’ll Experience

Where to Meet

Reviews

Location

Anne Arundel

Duration

2 hours

Number of Guests

1 - 15 guests

Language

English

Other

Vegetarian, Pet-friendly

Digital Ticket

Mobile or paper ticket accepted

Explore historic Annapolis with a twist on this 2-hour pub crawl. Sip on-recommended drinks (extra cost) while diving into tales of rebels and rum-runners. Perfect for history and whiskey fans!

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

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.
Read more

Reviews

5.0

based on 36 reviews

(TripAdvisor)

So fun and interesting!

July 18, 2026

Ryan knows his stuff! A great experience! Highly recommended!!

(TripAdvisor)

LOVED!!!

July 18, 2026

If you’re coming to Annapolis this is a must! Even if you live here - we learned so much, had so fun, had some delicious cocktails and met some new friends!

(TripAdvisor)

Great tour

July 14, 2026

Ryan was great! Knew his stuff. Would do it again!

(TripAdvisor)

So fun!

July 11, 2026

We had so much fun! Ryan told such good stories and it was so interesting. It was laid back and just a good time. I highly recommend!

(TripAdvisor)

Drinking tour?! Yes!!

July 04, 2026

Very fun and informative! Ryan knows his history and drinks. A glimpse into a different type of Annapolis history.

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Experience Details

What You Get

Good To Know

What You’ll Experience

Colonial Annapolis Historic District

Meeting & Pickup

Cancellation PolicyCancel your booking at least 24 hours before the experience start time to receive a full refund.Read more

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