NYC: Speakeasy Drinks and Prohibition History Tour

Imagine strolling through Midtown Manhattan, stepping into hidden bars that once kept America’s secret during Prohibition. This 3-hour guided walking tour takes you to three historic speakeasies, offering skip-the-line access to some of the city’s most iconic and clandestine drinking spots. Led by engaging guides, you’ll learn about the Gilded Age, Prohibition, and the city’s vibrant nightlife revival, all while sipping on expertly crafted cocktails. The tour ends in the bustling Times Square area, perfectly positioned for a night out or a brief sightseeing detour.

What we love most is the authenticity of the venues—each with its unique decor and vibe—and the knowledgeable guides who bring the era to life with stories of gangsters, bootleggers, and daring women. The inclusion of premium cocktails served by NYC’s top mixologists makes this experience all the more memorable. Plus, the skip-the-line entry means no wasting time waiting, so you’re straight into the good stuff.

A potential consideration? The cost of drinks is not included in the ticket price, and some cocktails can run from $18 to $25. That said, many reviews note that the quality and creativity of the drinks make it worth the extra expense. This tour is best suited for history buffs with a taste for cocktails, social travelers eager for a fun night, and anyone curious about New York’s secret bars and lively past.

Key Points

• Historic venues: Visit three carefully selected speakeasies with distinct personalities and stories.
• Expert guides: Guides like Katherine, Ariel, and Ryan keep the history engaging and fun.
• Premium cocktails: Sample top-notch drinks crafted by NYC’s best mixologists, though expect to pay extra.
• Authentic atmosphere: Experience the ambiance of prohibition-era NYC with vintage decor and clandestine settings.
• Educational and social: Learn about the social movements, gangsters, and women of the Gilded Age while mingling with fellow travelers.
• Flexible options: Cancel up to 24 hours in advance, keep your plans open, and book with confidence.

The NYC: Speakeasy Drinks and Prohibition History Tour is an adventure that combines history, culture, and a bit of nightlife magic. It’s designed for those who want more than just a bar crawl—it’s a journey into the secretive world of Prohibition-era New York, told through the lens of its most iconic venues.

Starting at 825 8th Avenue, your guide greets you outside the One Worldwide Plaza building on 8th Avenue, with the American flag fluttering above and a bike rack in front. From there, the tour unfolds as a walk through Midtown Manhattan, where each stop is carefully chosen to reflect a different aspect of the era—criminal, social, and cultural.

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The Itinerary Breakdown

First Stop: A Classic NYC Bar

Your journey begins at a bar with roots dating back to the Prohibition era, a place that has survived gangster rivalries, law enforcement crackdowns, and changing tastes. This venue often features old-school decor, vintage photographs, and a sense of stepping back in time. As one reviewer fondly remembers, “This bar traces its roots to the period of notorious gangsters,” giving you a tangible link to history. Here, you’ll learn about the tough days when speakeasies operated in plain sight, often disguised as legitimate businesses.

Second Stop: Catalyst of Prohibition

Next, your guide takes you to a place that delves into the causes and consequences of Prohibition. This venue often showcases stories about women of the Gilded Age and the rise of influential figures like oil magnates. Several guests appreciated the engaging storytelling; one remarked, “Katherine was incredibly knowledgeable and engaging,” which keeps the history lively rather than dry. Expect a cozy, intimate space that reflects the social movements and societal shifts of the early 20th century.

Third Stop: The Resurgence of Nightlife

Finally, the tour concludes at a unique cocktail lounge that celebrates the end of Prohibition and the rebirth of New York’s nightlife. It’s a spot where stories of the ban’s dramatic end are shared, along with tales of the city’s vibrant post-Prohibition era. This venue often features creative cocktails and a lively atmosphere, perfect for finishing your evening in style.

What to Expect at Each Venue

While the walking portion lasts approximately 3 hours, the focus is on quality, not quantity. Expect to walk at a moderate pace, with some venues requiring you to climb stairs or squeeze into intimate settings—so comfortable, yet smart attire is recommended.

At each stop, you’ll be seated and served premium cocktails crafted by NYC’s top mixologists. Reviews consistently praise the deliciousness of drinks—some say they’re worth the extra cost, with cocktails priced between $18 and $25. You might find a classic Manhattan, a creative twist on a gin fizz, or a modern take on a whiskey sour. Many guests report the drinks as “interesting and tasty,” with some even sharing that their guides recommended excellent options when overwhelmed.

The venues themselves are carefully chosen to reflect historic authenticity and ambiance. Expect vintage decor, dim lighting, exposed brick, and a sense of secrecy that transports you back to the 1920s. Guides like Ariel and Ryan are praised for their enthusiasm, storytelling, and ability to personalize the experience, making each venue feel special.

The Value of the Experience

At first glance, the tour price might seem steep given that drinks are extra. However, reviews highlight the value of the experience—the knowledge, access to exclusive venues, and quality cocktails justify the cost. Several mention that the guides’ storytelling and the chance to explore hidden NYC bars make it a worthwhile investment.

Plus, the social aspect shines through. Many guests mention meeting fun, like-minded travelers from around the world, making the tour not just educational, but also a great way to connect. One reviewer summed it up: “We met fun people and enjoyed fancy cocktails together,” emphasizing that this tour is as much about the atmosphere and camaraderie as it is about history.

Practical Details and Tips

• Duration: 3 hours, including walking and stops
• Meeting Point: Outside One Worldwide Plaza, 8th Avenue between 49th and 50th Street
• Price: Tour price is separate from drinks; expect cocktails from $18 to $25
• Reservation: Book now, pay later; cancel up to 24 hours in advance
• What to bring: Valid ID or passport, comfortable shoes, and a bit of cash for drinks
• Dress code: Smart casual—no flip-flops, ripped clothing, or large bags
• Participants: Must be 21+ and able to walk at a moderate pace
• Language: Conducted in English, with guides noted for their engaging storytelling

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Who Will Enjoy This Tour?

This experience appeals most to history buffs, cocktail lovers, and social travelers. If you’re interested in how America’s alcohol ban shaped culture and want to sip cocktails in atmospheric venues, you’ll find plenty to love. It’s especially great for those who appreciate stories of gangsters, women’s movements, and post-Prohibition revival.

It’s also ideal if you prefer small group settings where guides can personalize stories and answer questions. Because of the walk and venue sizes, it’s better suited for those with decent mobility and a smart outfit.

This tour offers a well-rounded glimpse into New York City’s clandestine past, blended with the pleasures of sampling premium cocktails. The guides’ passion and knowledge shine through, making each stop feel like a private lesson with a friend who just happens to be a cocktail connoisseur and historian. The venues are thoughtfully chosen, giving you a taste of authentic Prohibition-era ambiance without the need for secret passwords.

If you’re looking for a fun, educational, and social way to spend an evening in Manhattan, this tour fits the bill. It’s perfect for those wanting to uncover hidden NYC gems, learn about a pivotal era, and enjoy some of the city’s best drinks.

For anyone eager to combine history with a lively night out—without breaking the bank—this experience is a solid choice. Just remember, the cocktails are part of the adventure, so budget accordingly and come ready for a memorable evening.

Is this tour suitable for non-drinkers?
While the focus is on cocktails, non-alcoholic options may be available, but the experience mainly revolves around tasting premium drinks. It’s best suited for those comfortable with alcohol consumption.

How much walking is involved?
You’ll walk at a moderate pace for about three hours, stopping at three venues. The walking isn’t strenuous, but comfortable shoes are recommended.

Are the venues accessible for people with mobility issues?
Unfortunately, the tour isn’t suitable for those with mobility impairments due to venue layouts and walking involved.

What’s included in the tour price?
The ticket covers the guided tour and skip-the-line access to three bars. Drinks are purchased separately, with cocktails costing roughly $18 to $25.

Can I cancel my booking?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans change.

Is there an age restriction?
Yes, participants must be 21+ and show valid ID or passport.

Will I learn new things about New York?
Absolutely. Guides share stories about Prohibition, gangsters, and the city’s social movements, making history engaging and relevant.

Can I join if I’m a local New Yorker?
Yes, many locals find this tour a fun way to rediscover their city’s history and hidden bars, as noted in reviews from residents.

Are the cocktails included in the tour price?
No, drinks are paid for separately. Expect to spend around $18–$25 per cocktail, but many guests agree the drinks are worth it.

This tour offers a lively, authentic peek into NYC’s past with the added bonus of fantastic cocktails and lively storytelling. Perfect for history lovers and nightlife fans alike, it’s a memorable way to see the city from a different perspective.

You can check availability for your dates here: More Great Tours Nearby