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.

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).

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Step-by-step itinerary

Day 1 — 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.

Top questions

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.