NYC: Prohibition Speakeasy Tour & Manhattan Rooftop Bars

Walk Times Square sip cocktails hear real prohibition stories

You’ll slip into secret NYC speakeasies with express entry, taste classic cocktails where history lingers in every corner, and hear real Prohibition-era tales from your local guide. Expect rooftop skyline views, unexpected friendships over drinks, and stories that stay with you long after you leave Manhattan’s bright lights behind.

Step-by-step itinerary

Explore NYC history and speakeasies

• Walk through historic Times Square
• View Manhattan skyline from rooftop lounge
• Pass by Broadway shows and restaurants
• Hear immigrant stories from Prohibition Era

The experience

I didn’t think I’d ever walk into a bar through a hidden door behind a wall of books, but that’s how our night started in Manhattan. Our guide, Alex, had this way of telling stories that made you feel like you were right there in the middle of the 1920s. I swear you could almost smell old whiskey soaked into the wood. We met up near Times Square, which was buzzing as usual, but once we ducked down a side street it felt like a different city. There was this moment when Alex pointed out an old neon sign. He said it survived decades of change, and I caught myself wondering about all the people who’d walked past it before us.

The first speakeasy was dim and kind of cozy, with jazz playing softly (not the cheesy kind). I ordered something called a Bee’s Knees: honestly, no idea what was in it but it tasted sharp and sweet at the same time. The bartender winked when I tried to guess the ingredients. We swapped stories with some folks from Brooklyn and a couple visiting from Spain. Everyone loosened up after that first round. It’s funny how fast strangers become friends when you’re sharing secrets over drinks.

Later, we climbed up to a rooftop lounge for these wild views of the Manhattan skyline: Empire State Building right there in front of us, lights flickering against the clouds. The air was chilly but fresh, and someone laughed when their hair blew everywhere (mine included). Alex told us about immigrant families who ran bars during Prohibition, risking everything just to keep their doors open. That part stuck with me more than I expected. By the third bar my feet were tired but my head was buzzing, not just from cocktails but from all those layered stories about New York’s past.

What’s included

Your evening includes express entry and free admission at three historic NYC bars or speakeasies led by a dedicated licensed guide who shares Prohibition-era stories as you go, plus panoramic rooftop views and plenty of time to enjoy cocktails (drinks not included).

Options for this experience

5 options

7:30pm TourGuide in English · 19:30Night tour at the 7:30pm session

6:30pm TourGuide in English · 18:30

5:00pm TourGuide in English · 17:00

See 2 more options

7:00pm TourGuide in English · 19:00

4pmGuide in English · 16:00

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery day5 departure times: the first at 16:00, the last at 19:30

Book up toStart time

AgesAdult (21 and older) · Under 21: can't be included in the booking

GroupUp to 15

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Moderate physical levelNot for pregnant travelersNot for heart conditionsNot for back problems

Operated by Telltale Tours

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long does the NYC speakeasy tour last?

The experience lasts around three hours in total.

Are drinks included on this NYC speakeasy tour?

The tour includes entry to each bar. Drinks are available for purchase separately.

Is there hotel pickup for this Prohibition tour?

No hotel pickup is included. You meet your guide near Times Square.

How many bars or speakeasies do we visit?

You’ll visit at least three iconic bars or speakeasies during the evening.

What should I wear on this Manhattan bar tour?

The dress code is upscale casual: no sportswear or ripped clothing allowed.

Is this tour suitable for people with limited mobility?

This experience isn’t recommended for travelers with spinal injuries or poor cardiovascular health.

Will there be a local guide throughout the evening?

Yes, you’ll have a dedicated licensed host/guide leading your group all evening.

Does the tour include express entry to bars?

Yes, free admission and express entry are included at each location visited on the route.