Private Speakeasy Adventure A Tipsy Trip through History in New York
New York, United States

Private Speakeasy Adventure A Tipsy Trip through History

Outty Ranking 54 5.0 · 7 traveler reviews3 hoursFrom $68

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September 2026

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Adults

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Age 12 and under

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Outty Ranking

54/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Speakeasy Adventure A Tipsy Trip through History worth booking?

Private Speakeasy Adventure A Tipsy Trip through History is a 3-hour experience in New York, United States, from $68 per person. It scores 54 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 5/5 rating across 7 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.

Outty Ranking
54 / 100
Rating
5/5 (7)
Duration
3 hours
From
$68 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. Consid

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

    • Rich storytelling about the Prohibition Era in New York City
    • Visit to three historical and iconic NYC bars and speakeasies
    • Guides (English)
    • Free admission, express entry and preferred customer treatment at venues

    Not included

    • Alcoholic/non-alcoholic drinks (available to purchase)
    • 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.

    2. Theater District

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

    3. Hell's Kitchen

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

    4. Studio 54

      NYC's most iconic dance club

      Pass by without stopping

    Where it starts and ends

    Meeting point

    New York

    Your host will meet you on 8th Avenue between 49th Street and 50th Street outside the office building entrance to One Worldwide Plaza. On 8th Avenue, there is a bike rack in front and Carnegie Diner is visible across the street. The host will be holding a binder with Telltale Tours clearly visible.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Returns to the starting point

    Before you book

    Cancellation
    All sales are final. No refund is available for cancellations.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Mon, Tue, Wed, Thu, Fri, Sat
    Group size
    Up to 15 travelers per booking
    Operated by
    Telltale Tours

    Know before you go

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

    Photos

    Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 2Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 3Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 4Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 5Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 6Private Speakeasy Adventure A Tipsy Trip through History in New York, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 7 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    4 mentions

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

    Traveler reviews

    7 verified traveler reviews for Private Speakeasy Adventure A Tipsy Trip through History. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    7
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    0
    Sort
    Patti_S · May 2026

    Great experience!

    Our guide RYAN was THE BEST!!! It was our son’s graduation from NYU, and his birthday. We had 3 tourists, and 5 NYC residents. I was nervous because the speakeasy tour was the only thing I had planned for graduation/birthday night. . . The tour was everything I needed it to be AND MORE!!! Not hokey! Not “touristy”. A tour that even thoroughly impressed the locals! We had the BEST TIME!!! Thank you, Ryan!!!! 🫶🏻🫶🏻🫶🏻🫶🏻🫶🏻. We hope we got your part!

    Response from the operator: We are glad you enjoyed the experience. We agree that Ryan is great and also hope he gets the part. All of our hosts/storytellers are performers so we look forward to losing them to Broadway stardom some day soon!

    via Viator

    CrownMajesty · April 2026

    A great learning experience

    Julian was great. I totally recommend for a great time.

    via Tripadvisor

    cushlae2026 · February 2026

    Speakeasy tour is a must when in New York

    Wow! Julian was so amazing and fun! Highly recommend this tour - such a fun night in New York. Ask for Julian as your guide

    via Tripadvisor

    antoniel2026 · January 2026

    Pretty cool

    Julian was really cool guy, gonna miss him a lot. Even though he’s a jags fan he really seems like a good guy. Very rare for jags fans.

    via Tripadvisor

    nelliebloomnj · October 2025

    Great tour

    Great tour. Our tour guide was great. Highly recommend this if you want to learn about speakeasy bars in mid town. Really enjoyed it

    via Tripadvisor

    Good to know

    Duration
    3 hours
    Free cancellation
    Non-refundable
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Tue, Wed, Thu, Fri, Sat
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    2
    Verdict
    Worth a Look

    Why this scores 54

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

    Traveler sentiment (30% weight)81
    Review evidence (18% weight)26
    Booking momentum (14% weight)16
    Value for money (12% weight)75
    Listing quality (10% weight)85
    Local standing (8% weight)61
    Booking flexibility (8% weight)0

    Private 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 Private Speakeasy Adventure A Tipsy Trip through History cost?

    +

    Prices start at $68 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 Private 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 Private Speakeasy Adventure A Tipsy Trip through History worth it?

    +

    It holds an Outty Ranking of 54 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 7 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable culture & history in New York, and how flexible the cancellation terms are.

    Can I cancel or reschedule Private Speakeasy Adventure A Tipsy Trip through History?

    +

    No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.

    Is Private 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 Private Speakeasy Adventure A Tipsy Trip through History?

    +

    Around 2 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 Private 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 Grand Canyon VIP Helicopter Tour, Half-Day Bus Tour of NYC Top Highlights, NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports. 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.

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