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 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

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.

Options

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Reviews

5.00

7 reviews

Total reviews and rating from Viator & Tripadvisor

Great experience, 0erfect for out of town guests!
guymI4975RB,,Dec 30, 2025
- Review from Tripadvisor
5.00
This was such a fun experience! The drinks were great and the history behind everything made it so much fun. We had a group of friends visiting, and this was the perfect happy hour to show them downtown Annapolis. Would recommend to anyone (Ryan even accommodated the non drinker in our group).
So much fun!
matH4085LZ,,Dec 28, 2025
- Review from Tripadvisor
5.00
Annapolis is such a quaint town I wanted to visit with friends from out of town and didn't know where to start. The tour was a bargain and took all the pressure off figuring out what to do. It launched us into a memorable evening with great friends. The new perspective on American history was a bonus!
Local Annapolis Family
bradn996,,Dec 26, 2025
- Review from Tripadvisor
5.00
Excellent tour, Ryan is a very good story teller and gives great drink recommendations at every stop. Would highly recommend to do with a group of friends or family.
Awesome tour
T8962GSjf,,Dec 21, 2025
- Review from Tripadvisor
5.00
Our tour with Ryan Lyles was super! His knowledge of the history of alcohol and Annapolis was impressive. He's also matched different cocktails to different historic periods which made this tour most interesting and tasty!
Very Interesting
Flyer03335911077,,Dec 6, 2025
- Review from Tripadvisor
5.00
Ryan was a great tour guide! He was very knowledgeable about history and alcohol's impact. He also gave us tips on local places to try. I would highly recommend taking his tour!!
Super fun with a twist of Annapolis Flare / Education
L3769TVjaimej,,Nov 21, 2025
- Review from Tripadvisor
5.00
I had a great time on this whiskey tour in Annapolis! It was the perfect mix of fun with relaxing vibes, and really interesting information about the history of whiskey and vodka in Annapolis. The guide was super knowledgeable and friendly, and the tasting experience was great and having it be in local restaurants that I frequent made it even better. I highly recommend for anyone looking for a unique and cool outing!
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.