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A cocktail glass with a lemon slice, a bottle labeled "Prohibition O.F.", and a metal shaker on a bar counter. 1
Two anthropomorphic frogs dressed in 18th-century attire, holding a wooden mug with beer. 2
A brick building with a sign reading "Federal House Bar & Grill." 3
A man holding a wine glass in front of a large 'DRY 85' sign. 4
A street at dusk with buildings on either side, a church spire in the distance, and festive lights. 5

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

By Tipsy Bay Co.
10.0 out of 10
Exceptional
Free cancellation available
Price is CA $43 per adult
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Features

  • Free cancellation available
  • 2h
  • Mobile voucher
  • Instant confirmation

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 whisky 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 city centre, rain or shine, and prepare for a fun evening immersed in tipsy history.

  • 2-hour historical pub crawl through city centre 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

Activity location

  • Annapolis Historic District
    • Main Street
    • 21401, Annapolis, Maryland, United States

Meeting/Redemption Point

  • Galway Bay Irish Restaurant and Pub
    • 63 Maryland Avenue
    • 21401, Annapolis, Maryland, United States

Check availability

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

  • Activity duration is 2 hours2h
    2h
  • English
Language options: English
Starting time: 4:00PM
Price details
CA $42.62 x 1 AdultCA $42.62
Total
Price is CA $42.62
Until Thu, Jul 9

What's included, what's not

  • What's includedWhat's included
    A guided drinking history tour at iconic Pubs in Annapolis
  • What's excludedWhat's excluded
    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.

Know before you book

  • Service animals allowed
  • Public transport options are available nearby
  • Suitable for all physical fitness levels

Activity itinerary

Annapolis Historic District

  • 2h
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 whisky 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.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIES
    Annapolis Historic District
    • Main Street
    • 21401, Annapolis, Maryland, United States

Meeting/Redemption Point

  • PEOPLEPEOPLE
    Galway Bay Irish Restaurant and Pub
    • 63 Maryland Avenue
    • 21401, Annapolis, Maryland, United States

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