Discover the less touristy side of New York with this guided historical tour. Start at one of the city’s oldest bars, a Prohibition-era speakeasy, and see some iconic sites like The National Arts Club, Flatiron Building, and Gramercy Park. Finish the journey at The Flatiron Room where you can sip on a whiskey cocktail (not included in the price) and listen to jazz.

Both first-time and returning visitors will enjoy this tour
This tour offers a mix of NYC history and architecture
Get suggestions on where to go from your guide
Enjoy the camaraderie of a small-group tour

What To Expect

Pete’s Tavern

One of the oldest bars in the city, it was a speakeasy during Prohibition. One of the best places to experience the old New York. O.Henry, a famous American short story writer, used to work in the Tavern.
1 hour • Admission Ticket Free

Gramercy Park

The only private park in New York, it has a very interesting history which I’ll tell you about. Also, it allows views to the glorious Chrysler Building. Irving Place is named after Washington Irving, a writer and a historian, known for “The Legend of Sleepy Hollow” among other works.
10 minutes • Admission Ticket Free

The National Arts Club

One of the city’s private clubs open for members only. We can admire its beautiful facade from the outside
10 minutes • Admission Ticket Free

The Players

Another private club with a lot of history behind it.
10 minutes • Admission Ticket Free

Flatiron Building

One of the most picturesque buildings in New York City, it owes its unique appearance to its shape. Of course, there is more to its story than what meets the eye!
10 minutes • Admission Ticket Free

MetLife Building

The MetLife Tower used to be the tallest in the world in 1909. Also, look at those clocks!
10 minutes • Admission Ticket Free

Empire State Building

The most important building in NYC and one of the best known in the world. Our route will allow for some of the best views to the Empire State.
10 minutes • Admission Ticket Free

Madison Square Park

Lively city park which was the first home to the Madison Square Garden (thus, the name). The story of the second Madison Square Garden involves a beautiful woman, a love story and an actual murder.
5 minutes • Admission Ticket Free

Highlight

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Most travelers can participate
This tour/activity will have a maximum of 6 travelers

Include

See NYC highlights with a licensed NYC Guide
Enjoy the intimate atmosphere of a small group
Discover the city’s fascinating history and culture
Get insider suggestions for live jazz, speakeasies, and hidden spots
Get a free NYC map for your further city exploration

Exclude

Drinks and cocktails are fantastic but not included
Food is available but not included