The Speakeasy Adventure: A Tipsy Trip Through History in New York, United States
New York, United States

The Speakeasy Adventure: A Tipsy Trip Through History

Outty Ranking 82 4.8 · 257 traveler reviews3 hoursFrom $40
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Outty Ranking

82/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.8/5

Based on 257 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is The Speakeasy Adventure: A Tipsy Trip Through History worth booking?

The Speakeasy Adventure: A Tipsy Trip Through History is a 3-hour experience in New York, United States, from $40 per person. It scores 82 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.8/5 rating across 257 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
82 / 100
Rating
4.8/5 (257)
Duration
3 hours
From
$40 per person

Sip, swirl, taste, and gulp – it's time for a tipsy adventure through New York's underground watering holes! ️‍♀️ Get ready to embark on a journey that feels like stumbling upon secret oases amidst the midtown madness. Consider this your ticket to the hidden escapes from the tourist hustle and bustle. But that's not all – you won't just be roaming solo. Our exciting tour guides, the true masters of the art, will be your compass through this spirited expedition. ️ And oh, the history! Get ready to be enchanted by tales as old as time, as you sip on libations inspired by the past. So, gather your curiosity and an adventurous spirit – it's time to unlock the door to New York's hidden treasures and stories, one sip at a time. Let's dive into the spirited trails and make some history of our own! ️

What you get

    About this experience

    Sip, swirl, taste, and gulp – it's time for a tipsy adventure through New York's underground watering holes! ️‍♀️ Get ready to embark on a journey that feels like stumbling upon secret oases amidst the midtown madness. Consider this your ticket to the hidden escapes from the tourist hustle and bustle. But that's not all – you won't just be roaming solo. Our exciting tour guides, the true masters of the art, will be your compass through this spirited expedition. ️ And oh, the history! Get ready to be enchanted by tales as old as time, as you sip on libations inspired by the past. So, gather your curiosity and an adventurous spirit – it's time to unlock the door to New York's hidden treasures and stories, one sip at a time. Let's dive into the spirited trails and make some history of our own! ️

    What's included

    Included

    • Hosted by a local, professional and licensed guide
    • Free admission, express entry and preferred customer treatment at venues
    • Great storytelling of U.S. immigration and Prohibition Era history
    • Experience the ambience and mixology of three iconic NYC speakeasies and bars

    Not included

    • Alcoholic/non-alcoholic drinks (available to purchase. crdit card and processing fees may be added)
    • Gratuities

    What you'll see and do

    1. Times Square

      Visit historic Restaurant Row, NYC's hidden bars and the incredible lights and pageantry of Times Square.

      Pass by without stopping

    2. Theater District

      Home to the world's most famous Broadway shows and amazing restaurants. Walk down the famous Restaurant Row.

      Pass by without stopping

    3. Hell's Kitchen

      Recount the great immigration and Prohibition Era stories of this historic and notorious New York City neighborhood.

      Pass by without stopping

    Where it starts and ends

    Meeting point

    New York

    Meet on 8th Avenue between 49th Street and 50th Street outside the business entrance to One Worldwide Plaza. Do NOT go to the plaza behind the building.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Returns to the starting point

    Options you can book

    • 7:00pm Tour

    • 6:30pm Tour

      Duration: 3 hours

    • 7:30pm Tour

    • Afternoon Tours

    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
    Every day
    Group size
    Up to 10 travelers per booking
    Operated by
    Telltale Tours

    Know before you go

    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Travelers should have at least a moderate level of physical fitness
    • Minimum drinking age is 21 years old
    • Dress code is upscale casual. No sportswear or ripped clothing permitted.
    • A maximum of 10 people per booking
    • Participants must bring a government issued photo ID or a passport for proof of age

    Photos

    Speakeasies and Historic Bars, The Speakeasy Adventure: A Tipsy Trip Through History in New YorkStories of the Prohibition Era, The Speakeasy Adventure: A Tipsy Trip Through History in New YorkPremium Cocktails, The Speakeasy Adventure: A Tipsy Trip Through History in New YorkJoin the Group!, The Speakeasy Adventure: A Tipsy Trip Through History in New YorkThe Speakeasy Adventure: A Tipsy Trip Through History in New York, photo 6Meet New Friends, The Speakeasy Adventure: A Tipsy Trip Through History in New York

    What travelers are saying

    Outty’s summary of the themes that recur across 257 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    6 mentions

    Reviewers describe the commentary as informative rather than scripted.

    The guide

    4 mentions

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

    Food and drink

    4 mentions

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

    Traveler reviews

    257 verified traveler reviews for The Speakeasy Adventure: A Tipsy Trip Through History. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    235
    4 star
    9
    3 star
    8
    2 star
    3
    1 star
    2
    Sort
    jenraeder · October 2026

    Super fun tour!

    Such a fun thing to do in NYC and our guide Walter was amazing!!! Met some interesting people, experienced some cool bars and learned a lot about prohibition and the speakeasy scene. Highly recommend!

    via Tripadvisor

    lorreenm2022 · October 2026

    Ariel is awesome!

    Ariel was fantastic! Her knowledge of history was terrific! We truly enjoyed ourselves. Thank you 😊

    via Tripadvisor

    danielrK1636US · October 2026

    Epic tour good drinks

    Fantastic work from Ariel! Very fun tour, highly recommend!

    via Tripadvisor

    stevepT2174JV · September 2026

    Great fun and at the speakeasy's

    Ryan, was great fun and very knowledgeable regarding the history of prohibition. The bars selected were all different but all very interesting and a great vibe. Would do again and highly recommend.

    via Tripadvisor

    119LisaR · September 2026

    Speakeasy Fun!

    We had an amazing evening out in the city with our fabulous tour guide, Ariel! Ariel was knowledgeable, warm, fun, and entertaining as we made our way to three incredible speakeasy stops. We loved the vibes, drinks, food, an atmosphere at each, and I also appreciated plenty of mocktail options as a non-drinker. We learned a ton and had so much fun! Highly recc!

    via Tripadvisor

    Good to know

    Duration
    3 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    90
    Verdict
    Exceptional

    Who runs this experience

    Operated by Telltale Tours, who run 7 experiences we rank across 1 city, with an average Outty Ranking of 62.0.

    See everything Telltale Tours runs

    Why this scores 82

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

    Traveler sentiment (30% weight)85
    Review evidence (18% weight)71
    Booking momentum (14% weight)67
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)68
    Booking flexibility (8% weight)100

    The Speakeasy Adventure: A Tipsy Trip Through History: questions travelers ask

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

    How much does The Speakeasy Adventure: A Tipsy Trip Through History cost?

    +

    Prices start at $40 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in New York usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does The Speakeasy Adventure: A Tipsy Trip Through History take?

    +

    Plan for about 3 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 New York is not rushed.

    Is The Speakeasy Adventure: A Tipsy Trip Through History worth it?

    +

    It holds an Outty Ranking of 82 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.8/5 across 257 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in New York, and how flexible the cancellation terms are.

    Can I cancel or reschedule The Speakeasy Adventure: A Tipsy Trip Through 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 The Speakeasy Adventure: A Tipsy Trip Through History suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 3-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book The Speakeasy Adventure: A Tipsy Trip Through History?

    +

    Around 90 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 New York 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 New York and add a light layer if any part of the 3-hour experience runs outdoors or after sunset.

    Where does The Speakeasy Adventure: A Tipsy Trip Through 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 New York 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 New York?

    +

    New York has more bookable experiences than any other city on Outty, and the quality spread is brutal. Observation decks are commoditised, so we score them on timed-entry reliability and sunset slots. Food tours and borough walks are where the ranking really separates operators, and the top scores in the city all come from small-group guides. On Outty we rank every New York experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports, Half-Day Bus Tour of NYC Top Highlights, SoHo, Little Italy, and Chinatown Walking Tour in New York. 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 New York?

    +

    September to early November, and late April through June. 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 New York?

    +

    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 The Speakeasy Adventure: A Tipsy Trip Through History?

    +

    Included: Hosted by a local, professional and licensed guide; Free admission, express entry and preferred customer treatment at venues; Great storytelling of U.S. immigration and Prohibition Era history; and Experience the ambience and mixology of three iconic NYC speakeasies and bars. Not included: Alcoholic/non-alcoholic drinks (available to purchase. crdit card and processing fees may; and Gratuities. Always check the voucher for the final list before you travel.

    Where is the meeting point for The Speakeasy Adventure: A Tipsy Trip Through History?

    +

    Meet on 8th Avenue between 49th Street and 50th Street outside the business entrance to One Worldwide Plaza. Do NOT go to the plaza behind the building. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is The Speakeasy Adventure: A Tipsy Trip Through 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 The Speakeasy Adventure: A Tipsy Trip Through 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 The Speakeasy Adventure: A Tipsy Trip Through History if the weather is bad?

    +

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

    What do travelers say about The Speakeasy Adventure: A Tipsy Trip Through History?

    +

    Across 257 reviews averaging 4.8 out of 5, recurring themes include knowledge and storytelling, the guide, food and drink. Reviewers describe the commentary as informative rather than scripted.

    What booking options are available for The Speakeasy Adventure: A Tipsy Trip Through History?

    +

    There are 4 options to choose from, including 7:00pm Tour, 6:30pm Tour, 7:30pm Tour, Afternoon Tours. Prices and start times differ by option, so compare them on the booking screen.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for The Speakeasy Adventure: A Tipsy Trip Through History.

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