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Tipsy History Tour: 300+ Years of Annapolis Drinking History

Annapolis, United States 2h 5.0 · 48 reviews EN 5603826P1
Instant confirmation Free cancellation (24h) Mobile ticket Adults 21–120
Photos 8
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Overview

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

Tour at a glance

Duration
2h
01
Tour type
Group tour
up to 15 travellers per booking
02
Languages
EN
live guide
03
Pickup
Meet at start point
04
Operates
Mon, Tue, Wed, Thu, Fri, Sun
Starts 16:00
05
Confirmation
Instant
e-ticket by e-mail
06
Cancellation
Free up to 24h before
07
Traveller ages
Adults 21–120
08
Rating
5.0 / 5
49 verified reviews
09
Ticket
Mobile ticket
show it on your phone
10

What's included

  • A guided drinking history tour at iconic Pubs in Annapolis

Not included

  • Alcoholic beverages

Itinerary

  1. 1
    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.

    2h Admission free

Meeting & pickup

Everyone meets at the start point.

See the hostess at Galway Bay and let them know you are with us.

Schedule

Mon, Tue, Wed, Thu, Fri, Sun 16:00

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.

Traveller reviews

5.049 reviews
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49
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253wyattw Sep 2026 · Tripadvisor
Can’t Miss Tour in Annapolis

Such a fun tour! Ryan was delightful and a great storyteller. The history discussed is super interesting & quite funny. Worth it to anyone who likes a nice cocktail and good stories. Ryan is a can’t miss tour guide in Annapolis! And that’s on period.

Barberett Sep 2026 · Tripadvisor
History with drinks and laughter

We really enjoyed the stories of history and the alcohol that they drank in their time period. The bars were amazing. All of the group enjoyed it lots of information and lots of laughs and the period drinks were delicious . I highly recommend this tour. We all enjoyed ourselves. Thank you Ryan

juliamN9830MU Aug 2026 · Tripadvisor
Entertaining and so Fun!!

Ryan was so delightful!! He was funny and knowledgeable and told the stories in such an engaging way - not to mention he handled our sometimes rowdy group with such grace and really rolled with the punches to get us back on track! Seriously fun guy, great cocktails, turns out our history is wild and raucous and very tipsy! lol recommending to everyone!! Oh and we loved the maps Ryan!!!

Mark_K Aug 2026 · Viator
My girlfriend and I had...

My girlfriend and I had an amazing time on the Tipsy History Tour! Our tour guide was incredibly knowledgeable and did a great job making the history interesting, entertaining, and fun. We learned a lot about Maryland’s distilleries, Prohibition, and the history of Annapolis. Every pub we stopped at had amazing drinks and a great atmosphere. It was the perfect combination of history, drinks, and spending a fun afternoon together. We had a fantastic experience and would definitely recommend this tour to anyone looking for something fun and different to do.

bobrY6621JN Aug 2026 · Tripadvisor
Amazing experience

Fantastic tour. This was a great experience and well worth the money. Highly recommend

marktporter14 Aug 2026 · Tripadvisor
A Walking Happy Hour

Ryan’s tour is the best. A unique historical perspective on the Town of Annapolis from a drinking perspective. An important part of American History. It’s a great walking happy hour. Don’t miss it!

Julie_S Aug 2026 · Viator
Book this!

It’s a chill, fun experience. I learned so much, and had so much fun! Ryan is very knowledgeable about drinking history. Highly recommended.

Nichole_B Aug 2026 · Viator
This was a fun experience...

This was a fun experience with all sorts of rid bits about history about the area and the drinks we enjoyed. The guide was entertaining and very knowledgeable!

Reviews are collected by Viator and Tripadvisor from verified travellers.

Frequently asked questions

How long does this experience last?

It lasts 2h.

Is hotel pickup included?

Everyone meets at the start point.

Can I cancel for free?

Yes. Cancel up to 24 hours before the start time for a full refund.

Which languages is the guide available in?

Guide languages: EN

On which days does it run?

It runs Mon, Tue, Wed, Thu, Fri, Sun. Starts 16:00

How fast is the booking confirmed?

Instantly. Your e-ticket arrives by e-mail right after booking.

Is this a private tour?

No, this is a shared group experience.

Where do I complete the booking?

On viator.com, a Tripadvisor company, with live availability and secure payment. TourViaGo is a Global Partner of Viator.

Product code 5603826P1

Book on viator.com · Global Partner of Viator $39per person
Book now
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