The 9 Best New York City History Tours

1.NYC: Speakeasy Drinks and Prohibition History Tour

★★★★★★★★★★4.7 · 474 reviews · from $36Our pick

Spend three evening hours walking between three historic New York bars, lounges, and speakeasies. Your English-speaking guide connects Prohibition, Gilded Age reformers, bootleggers, and immigrant life with each stop. Guides such as Ariel, Ryan, Katie, and Katherine are known for lively storytelling and drink advice.

“Ryan was an amazing guide, we had a wonderful time learning about NYC history of alcohol.”

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2.The Original Greenwich Village Food & Cultural Tour Since 1999

★★★★★★★★★★5.0 · 254 reviews · 3 hours (approx.) · from $99Top rated

Walk Greenwich Village with guides such as Marie, Bert, Cindy, and Rick, stopping for pizza, tacos, Italian specialties, meatballs, gelato, and cannoli. The generous tastings make a full lunch, while stories, movie sites, Taylor Swift’s former house, and the Friends building add local color.

“What a great experience! I'd always heard Greenwich Village has good food, but just didn't know where to go. I'm so glad I did this tour to find a couple of must try places. The food was all excellent and very plentiful. It was hard to pick a favorite! Bert, our tour guide, was fun and very knowledgeable about the restaurants and the neighborhood. And at the end of the tour he also gave us ideas of things to do for the rest of the afternoon. I will definitely try another tour (Chinatown was highly recommended by both Bert and another couple in our group)!”

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3.The Speakeasy Adventure: A Tipsy Trip Through History

★★★★★★★★★★5.0 · 220 reviews · 3 hours (approx.) · from $38

Walk Midtown with a local guide such as Ryan, Ariel, Kate, Tim, or Emily, stopping at three bars tied to New York’s drinking past. Expect express entry, one complimentary drink, Prohibition stories, and a small group of up to 10. Bring ID, dress upscale casual, and budget extra for cocktails.

“We enjoyed the first two locations tremendously, but the third was a bit of a letdown - no place to sit, we were just brought in, given a beer and then left on our own pretty far from where we started. However, our guide was a 10 on the scale of 1 to 10 and we would book with her again.”

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4.Speakeasy Drinks and Prohibition History Tour NYC

★★★★★★★★★★4.5 · 204 reviews · 3 hours (approx.) · from $38

Walk through Midtown, Times Square, and the Broadway district with guides such as Ryan, Ariel, Julian, Katherine, and Walter. Visit three bars with different styles, hear stories of Prohibition and the Gilded Age, and buy your own cocktails along the way. Groups are capped at 18.

“Great tour, Julian was good fun and knowledgeable. Good fun and the cocktails and the speakeasy’s were fab”

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5.NYC: Night Out Prohibition History Bar and Speakeasy Tour

★★★★★★★★★★4.6 · 128 reviews · 3 hours · from $36

Walk from 825 8th Avenue to Times Square, visiting three Midtown bars, pubs, lounges, and speakeasies with an English-speaking guide. Expect stories about Prohibition, immigration, politics, and Midtown change, plus express entry and insider service. Bring ID and budget extra for drinks.

“The tour itself was fun and fascinating. Pur tour guide was very knowledgeable and easy going. The 3 venues were great and service was spot on. It was a perfect activity for my wife's 40th birthday with a group.”

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6.NYC: History of Slavery & Underground Railroad Walking Tour

★★★★★★★★★★4.7 · 87 reviews · 2h 30m · from $49

Spend 150 minutes walking Lower Manhattan with a licensed English-speaking guide. Visit the African Burial Ground National Memorial, former Underground Railroad sites, Fraunces Tavern, Trinity Church, and Wall Street while learning how African Americans shaped New York.

“The tour leader as well informed and passionate in sharing knowledge about the slave trade and Underground Railroad in NY. It sparked a desire to learn more and encourage to reserve a spot on this tour.”

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7.Soul of Harlem: Strivers Row, Apollo Theatre, Gospel History

★★★★★★★★★★4.6 · 87 reviews · 2 hours · from $49

Walk Harlem with a local English-speaking guide such as Altovise or Ron, tracing Ella Fitzgerald, Duke Ellington, and Harlem Renaissance landmarks. See Strivers’ Row, Bill’s Place, the Schomburg Center, and the Apollo Theater, with a Sunday gospel experience included on eligible tours.

“loved the concentrated area that was the focus of this tour. So much history, stories, and information. I had hoped to peek into the Apollo and not just hear, "here it is," even with the renovation going on. That would have added great depth, even at a greater charge.”

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8.New York: Mafia and Gangster History Tour in Little Italy

★★★★★★★★★★4.6 · 79 reviews · 2 hours · from $40

Walk one mile through Little Italy with guides such as Tom or Thomas, tracing Black Hand gangs, Lucky Luciano, John Gotti, police reformers, and mob murders. The two-hour tour uses historic photos, newspaper clippings, film locations, and a small group capped at 10 people.

“Paulie was an amazing tour host. We was enthusiastic about his lovely city and so informative. This is an amazing tour for all ages around Boston and I couldn’t recommend it more. Thank you Paulie!”

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9.New York City: Flatiron Food, History, and Architecture Tour

★★★★★★★★★★4.8 · 43 reviews · from $88

Spend three hours walking less than a mile through Flatiron and Union Square with a local English-speaking guide such as Justin or Jesse. Taste Roman-style pizza, a Reuben-inspired bagel, coffee, and award-winning pastries while learning about architecture, markets, and neighborhood history.

“What a fun day! Our guide was fantastic! She lead us on a wonderful journey through the Flatiron district that was fun and educational... wine, amazing food and wonderful conversation. We were all sad to have the tour end. I highly recommend this tour!”

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