Tipsy History Tour: 300+ Years of Annapolis Drinking History
Annapolis, United States

Tipsy History Tour: 300+ Years of Annapolis Drinking History

Outty Ranking 83 5.0 · 51 traveler reviews2 hoursFrom $39
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Outty Ranking

83/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 51 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tipsy History Tour: 300+ Years of Annapolis Drinking History worth booking?

Tipsy History Tour: 300+ Years of Annapolis Drinking History is a 2-hour experience in Annapolis, United States, from $39 per person. It scores 83 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 5/5 rating across 51 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
83 / 100
Rating
5/5 (51)
Duration
2 hours
From
$39 per person

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

    About this experience

    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's included

    Included

    • A guided drinking history tour at iconic Pubs in Annapolis

    Not included

    • Alcoholic beverages

    What you'll see and do

    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.

      120 minutes here

    Where it starts and ends

    Meeting point

    Annapolis

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

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Returns to the starting point

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Mon, Tue, Wed, Thu, Fri, Sun
    Group size
    Up to 15 travelers per booking
    Operated by
    Tipsy Bay Co.

    Know before you go

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

    Photos

    Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 2Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 3Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 4Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 5Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 6Tipsy History Tour: 300+ Years of Annapolis Drinking History, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 51 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    9 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    5 mentions

    The tastings and food stops are a highlight for most reviewers.

    The guide

    4 mentions

    Travelers single out the guide as the reason the experience works.

    Value for money

    2 mentions

    Travelers feel they got more than they paid for.

    Traveler reviews

    51 verified traveler reviews for Tipsy History Tour: 300+ Years of Annapolis Drinking History. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    51
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    0
    Sort
    Patti_H · October 2026

    Informative great drinks great tour guide

    Ryan was our Tipsy tour guide. He gave his great insight of the history of cocktails and many of the different establishments in Annapolis. He did a great job explaining things and getting us to try a few different bars and their signature cocktails of that era. I highly recommend Ryan as he is a great tour guide.

    via Viator

    Heather_L · October 2026

    Fun

    He was very knowledgeable about whiskey and the history and we had a great time. Didn’t feel rushed and enjoyed a few drinks!

    via Viator

    253wyattw · September 2026

    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.

    via Tripadvisor

    Barberett · September 2026

    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

    via Tripadvisor

    juliamN9830MU · August 2026

    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!!!

    via Tripadvisor

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Tue, Wed, Thu, Fri, Sun
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    18
    Verdict
    Exceptional

    Why this scores 83

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)91
    Review evidence (18% weight)75
    Booking momentum (14% weight)69
    Value for money (12% weight)70
    Listing quality (10% weight)85
    Local standing (8% weight)88
    Booking flexibility (8% weight)100

    Tipsy History Tour: 300+ Years of Annapolis Drinking History: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Annapolis.

    How much does Tipsy History Tour: 300+ Years of Annapolis Drinking History cost?

    +

    Prices start at $39 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Annapolis usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Tipsy History Tour: 300+ Years of Annapolis Drinking History take?

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    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Annapolis is not rushed.

    Is Tipsy History Tour: 300+ Years of Annapolis Drinking History worth it?

    +

    It holds an Outty Ranking of 83 out of 100, which we label "Exceptional". That score blends traveler sentiment (5/5 across 51 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Annapolis, and how flexible the cancellation terms are.

    Can I cancel or reschedule Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Tipsy History Tour: 300+ Years of Annapolis Drinking History suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    Around 18 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Annapolis can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Annapolis and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Tipsy History Tour: 300+ Years of Annapolis Drinking History start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Annapolis within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Annapolis?

    +

    Annapolis, MD packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Annapolis by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Annapolis experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Annapolis Historic Walking Tour: Harbor and Colonial Downtown, Historic Annapolis Food Tour, Historic Annapolis Walking Tour - Small Group Guided Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Annapolis?

    +

    Spring and fall bring the best weather and lighter crowds in Annapolis, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Annapolis?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

    What is included in Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    Included: A guided drinking history tour at iconic Pubs in Annapolis. Not included: Alcoholic beverages. Always check the voucher for the final list before you travel.

    Where is the meeting point for Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    See the hostess at Galway Bay and let them know you are with us. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Tipsy History Tour: 300+ Years of Annapolis Drinking History offered in?

    +

    It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    What happens to Tipsy History Tour: 300+ Years of Annapolis Drinking History if the weather is bad?

    +

    It generally runs rain or shine, so dress for the forecast in Annapolis. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Tipsy History Tour: 300+ Years of Annapolis Drinking History?

    +

    Across 51 reviews averaging 5.0 out of 5, recurring themes include knowledge and storytelling, food and drink, the guide. Reviewers describe the commentary as informative rather than scripted.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Tipsy History Tour: 300+ Years of Annapolis Drinking History.

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