Discover New York that tourists don't usually get to see. This tour starts in one of the oldest bars in New York that used to be a Prohibition-era speakeasy. We'll stroll around the Gramercy/Flatiron neighborhoods and see the only private park in Manhattan, beautiful 19th-century mansions, and iconic New York skyscrapers. I’ll share some of my favorite New York tales filled with daring, ambition, movie characters, love, murder, prohibition, and ladies' skirts.
16:00 - 16:15 PM Meeting and introductions
16:15 - 17:00
- Pete's Tavern and the history of Prohibition
Arguably the oldest bar in the city, it was a speakeasy during Prohibition. The Tavern stayed in its original form since the 19th century - it's one of the best places to experience the feel of old New York. We will spend some time in the bar soaking up the atmosphere over a drink and talking about the Prohibition, speakeasies, jazz age, famous writers, and history of New York.
- Gramercy Park
This charming little park can only be enjoyed from the outside . . . unless you happen to have a key. The general public is welcome to stroll around or stare into the park through the fence but is not allowed in. Gramercy Park has a rare distinction of being the only private park in Manhattan.
- Gramercy Neighborhood
The Gramercy neighborhood was developed in the 1830s and pretty much stayed that way; walking through it feels like time-traveling back into the Gilded Age. We will see beautiful architecture, I'll tell you the stories of famous actors, writers, architectural masterpieces, outrageous parties, assassinations, mayoral lamps, and failed presidential elections.
- Flatiron Building
One of the first New York City skyscrapers, the Flatiron is an iconic New York building famous for its triangular shape. It appears in many photographs, postcards, and, of course, movies. In the Spider-Man movies, it is depicted as the headquarters of the Daily Bugle, where Peter Parker works as a freelance photographer.
- MetLife Building
A beloved New York City silhouette, it was the tallest building in the world in 1909.
- Empire State Building
The most famous of all New York City skyscrapers, the Empire State became the tallest in the world in 1931 and stayed this way for 41 years! We'll get to the vantage point that allows the best views of the Empire State Building.
- Madison Square Park, the New York Life Building, Fifth Avenue, Broadway, etc. I'll tell you the stories of the Ladies Mile, the first Madison Square Garden, and the story of sensational murder that shook the nation in 1906.
Madison Square Park
Friendly Licensed NYC Guide
Suggestions for your future explorations of New York City
Information on jazz venues and speakeasies
Drinks and food
Please, contact me if you'd like to book a tour on a non-working day, I can be flexible.
- If you like history, this tour is for you! There will be a lot of stories of 19th century New York, Prohibition, the Jazz Age, and skyscrapers.
- The area we will be visiting is not usually visited by tourists but it's uniquely beautiful and very interesting.
- The tour lasts from 2 to 2.5 hours depending on the weather conditions (if it's nice outside, we walk slower and talk longer) and on your time.
- If you wish to visit another speakeasy (this time a contemporary one!) for fancy cocktails and an intriguing interior, please, let me know in advance, I'll make reservations and adjust our schedule.
- If you wish to conclude the tour in a jazz venue, please, inform me in advance so that I could make arrangements. This is an additional option with extra cost, please, see the "extras" section.
Iren was friendly, on-time, knowledgeable, enthusiastic, well-prepared, and just a joy to spend time with. By the end of our time with her we felt like we were seeing the city with a good friend. We had told her what we were interested in seeing, and she set it all up in a very logical order. We has such a good time with her.
Dear John and Elaine, thank you! It was a joy exploring the city with you, and - you took the words right out of my mouth - it did feel like spending time with friends. I'm very happy you had a good time in New York and hope you'll come back to visit again, there are just too many stories left to tell!
Our tour with Iren was absolutely awesome! She was very friendly and accommodating, and extremely knowledgeable of all the sites we visited. She made our experience most enjoyable, and gave us an appreciation of the city that we otherwise may not have had. I highly recommend Iren for any tour when you are in New York. We will definitely be looking her up again and will recommend her to everyone! Thank you Iren for an unforgettable day! ❤️
Dear Christie, thank you so much for your warm words, for choosing my tour and for being such a fun group! You made it a pleasure to share my enthusiasm for New York with you. We did have a wonderful day! There is so much more to see and do in the city; I hope you will come again and hope I can be a part of your next visit!