NYC: Speakeasy Drinks and Prohibition History Tour

The NYC Speakeasy Drinks and Prohibition History Tour offers a captivating glimpse into the city’s lively past, blending history, culture, and cocktails into a compact 3-hour experience. Led by engaging guides, you’ll visit three historic bars—each with its own story—and uncover tales of gangsters, bootleggers, and the city’s underground nightlife. With skip-the-line access and a lively group atmosphere, it promises both entertainment and education.

What really shines here is the blend of storytelling and authentic spots, giving you a taste of the city’s rebellious spirit during the Prohibition era. Plus, the chance to sample some interesting cocktails—though drinks are not included in the price—is a bonus for those curious about NYC’s storied drinking culture. The only catch? The tour involves a fair amount of walking and standing, so it’s best suited for those who enjoy active outings and have a reasonable level of mobility. Perfect for history buffs, cocktail enthusiasts, and anyone wanting to see a different side of Manhattan.

Key Points

• Authentic Experience: Visit three iconic and historic bars, each with its own unique vibe.
• Educational & Fun: Learn about the Prohibition era, gangsters, and the rise of NYC nightlife from knowledgeable guides.
• Skip-the-line Access: No long waits at venues, allowing more time to enjoy the atmosphere.
• Social Atmosphere: A lively group setting that’s great for meeting fellow travelers.
• Cost & Value: For $36, you get a well-rounded, engaging cultural experience—drinks are extra but reasonably priced.
• Ideal for: History lovers, nightlife explorers, and those seeking an interactive way to learn about NYC’s past.

An In-Depth Look at the Tour Experience

Starting Point & Meeting Logistics

The tour kicks off on 8th Avenue between 49th and 50th Streets, right outside the entrance of One Worldwide Plaza. The meeting spot is marked by a large American flag and the nearby Carnegie Diner, making it easy to find. The location is in central Midtown Manhattan, close to many hotels and attractions, which adds to the convenience.

Travelers should arrive with a valid ID—passport or driver’s license—and be ready for a walk. The group usually gathers outside on the sidewalk, where friendly guides greet everyone and set the tone for a relaxed, social outing. It’s a good idea to wear comfortable shoes and dress in a manner fitting the city’s stylish vibe, as the walking is moderate but steady.

The Itinerary Breakdown

Stop 1: Historic Bar with Gangster Roots
Your first stop is a bar with roots tracing back to the Prohibition era, notorious during the 1920s for its ties to gangsters and bootleggers. Here, the guide will share stories of infamous figures like Al Capone and how NYC’s underground bars operated in secrecy. Expect to see vintage decor, dim lighting, and a sense of stepping back in time. Guests have raved about the guide’s storytelling skills, with reviews highlighting guides like Arielle as particularly knowledgeable and engaging.

Stop 2: Catalyst of Prohibition & Women’s Role
The second venue explores the movement that led to Prohibition, including the role of women during the Gilded Age. This stop provides insight into the social and political factors that sparked the alcohol ban, along with the rise of influential figures like oil magnates. The atmosphere here is often more covert, with a secretive vibe that perfectly captures the era’s clandestine bar scene. Visitors appreciated the detailed historical context, which made the experience feel authentic and educational.

Stop 3: Resurgence & Modern Speakeasies
The final visit is a contemporary cocktail lounge that pays homage to the speakeasy style, but with a modern twist. Here, stories focus on how nightlife in NYC rebounded after Prohibition’s end and how the city’s bar scene has evolved into a vibrant, iconic part of its identity. Many reviewers mention the high-quality cocktails and the lively, welcoming ambiance—some even note being invited to continue socializing after the tour.

What You Can Expect During the Walk

Throughout the three hours, you’ll traverse Midtown’s streets, learning about the city’s immigrant stories and how New Yorkers historically fought to enjoy their drinks in defiance of the law. The guided commentary is lively and informative, peppered with tales of infamous gangsters and the social movements that shaped the era.

The pace is moderate, allowing plenty of time to soak in each location, snap photos, and chat with fellow travelers. The size of the group is typically small enough to foster a friendly atmosphere but large enough to add a lively energy. Reviewers have consistently praised guides like Ryan, Walter, and Katherine for their storytelling skills and ability to make the history come alive.

Drink & Food Considerations

Drinks are not included in the ticket price but are available for purchase at each venue. Expect prices ranging from $10 to $25 for cocktails, wine, or beer. Reviewers note that the drinks are well-crafted, with some guides offering excellent recommendations—like Walter’s suggestion of a particular cocktail that became a highlight of some guests’ night. The tour is designed as a social experience, so it’s worth budgeting for a few drinks to really enjoy the vibe.

The Cost & What You Get for $36

At $36, this tour offers solid value given the combination of skip-the-line access, expert guides, and the chance to learn about NYC’s Prohibition history firsthand. Compared to paying for individual drinks or separate tours, this experience offers a curated, social introduction into a fascinating chapter of American history. Plus, the guides’ storytelling and the historic atmospheres significantly enhance the value.

Reviews & Real Traveler Insights

From the glowing reviews, it’s clear that guides like Arielle and Ryan make a difference, blending humor, knowledge, and friendliness. Many travelers mention how they felt comfortable, with some even extending their evenings afterward to continue exploring with newfound friends.

Reviewers also appreciated the mix of historical info and fun facts, with some noting that the tour is ideal early in their trip to get ideas for future nights out. One traveler described it as “the best night in NYC,” thanks to the group’s energy and the guide’s engaging storytelling. The diversity of venues keeps the experience fresh, with each bar offering a different vibe—from vintage gangster hideouts to sleek modern speakeasies.

Accessibility & Practical Tips

Since the tour involves walking and standing, it’s best suited for those in reasonable physical condition. Wear comfortable shoes and be prepared for weather changes, as most of the walk is outdoors. Remember to bring a valid ID, especially if you’re a non-U.S. traveler, since ID checks are required.

If you’re planning to indulge, budget for drinks beforehand or at the venues. Also, avoid large luggage or oversized bags, as these aren’t allowed at the venues. The tour ends back at the starting point, making it easy to continue exploring Times Square or other nearby attractions.

Who Will Love This Tour?

This experience is perfect for history enthusiasts eager to connect the dots between NYC’s past and its present nightlife. It’s equally suited for cocktail lovers wanting to taste expertly mixed drinks in historic settings. Social butterflies will enjoy the lively group atmosphere, while travelers interested in local stories and gangster tales will find plenty to fascinate. Keep in mind, it’s not ideal for those with mobility issues or under 21.

Final Thoughts

The NYC Speakeasy Drinks and Prohibition History Tour delivers a well-paced, entertaining glimpse into one of the city’s most intriguing eras. Combining storytelling, historic venues, and social fun, it stands out as a meaningful way to spend an evening in Midtown Manhattan. While drinks are an extra cost, the overall experience—guided by passionate, knowledgeable storytellers—is a fantastic value for those curious about NYC’s underground world.

This tour is especially recommended for those who want a lively, educational outing that combines history, culture, and a bit of nightlife sparkle. Whether you’re in town for a few days or seeking a memorable night out, it offers a charming, authentic slice of New York’s past with plenty of stories to tell.

FAQ

Are drinks included in the tour price?
No, drinks are not included. They are available for purchase at each venue and generally cost between $10 and $25.

Where does the tour start?
It begins on 8th Avenue between 49th and 50th Streets, outside the entrance of One Worldwide Plaza, marked by a large American flag.

How long does the tour last?
The tour lasts approximately 3 hours, with a moderate walking pace and time to enjoy each venue.

Is the tour suitable for children or those under 21?
No, it’s designed for participants 21 and over, as alcohol is involved.

Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is the tour accessible for those with mobility issues?
No, it is not suitable for people with mobility impairments due to walking requirements.

What should I bring?
A valid photo ID is necessary, especially for non-U.S. citizens. Comfortable shoes and weather-appropriate clothing are recommended.

Will I meet the guides outside or inside?
You’ll meet outside the designated starting point on 8th Avenue. Guides are friendly and ready to welcome you.

Can I extend my night after the tour?
Absolutely! Many guests choose to explore more of Times Square or nearby bars after the official end.