- Tours›
- Off the Beaten Path
Flatiron and Gramercy - History and Architecture Tour
Joined 2021
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.
Itinerary
This itinerary can be customized to meet your needs and preferences. Send me a message with your requests!
Meeting Point
Pete's Tavern
Inside Pete's Tavern
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.
----------------
17:00 - 17:30 Gramercy Neighborhood
- 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.
17:30 - 18:00 (18:30) Flatiron Neighborhood
- 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.
Ending Point
Madison Square Park
Want to personalize this tour?
This tour can be customized to meet your needs and preferences. Click below to send me a message with your requests.
Inclusions & Exclusions
Friendly Licensed NYC Guide
Suggestions for your future explorations of New York City
Information on jazz venues and speakeasies
Drinks and food
Tour Important Information
- 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.
Important message from the supplier
Please, contact me if you'd like to book a tour on a non-working day, I can be flexible.
Cancellation Policy
- Free cancellation - 8 days prior to meeting time
- 50% Refund - 3 to 7 days prior to meeting time
- No Refund - Within 2 day(s) prior to meeting time
Joined 2021
About Tour Guide Iren G.
I fell in love with New York the moment I set foot here. It's been over 30 years now. I love this city so much that I became an NYC tour guide.
I enjoy showing people different faces of NYC - from the bustling city of skyscrapers to the quiet streets of out-of-the-tourists-way neighborhoods. I love telling stories of people who made New York what is it - the self-made millionaires, famous writers, daring architects, beautiful and powerful women. I can show you major landmarks as well as secret spots and cozy old bars where you can feel NYC history. I can take you to places where sounds of jazz rule the night and people swing-dance - a dance which was born in Harlem, NY, and had swept the world with its infectious joy.
I'm a licensed sightseeing guide with many years of experience. I'm truly fascinated with the unique history of New York City and love to share my passion for it. I've studied History of Art at Harvard Extension School (Cambridge, Mass) and New School (NYC) and took classes on NYC Architectural History at Cooper Union (NYC).
Reviews
“Wonderful, marvelous tour”
Iren was knowledgeable, kind and very thorough! She showed, explained, enlightened and discovered fabulous icons and places in New York. She anticipated our needs and was very accommodating. She is exceptional!
Iren G.
Thank you so much for your kind words! I really appreciate it!
“Like sightseeing with a good friend!”
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.
Iren G.
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!
“Absolutely awesome!”
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! ❤️
Iren G.
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!
$220/ per group
More tours by Iren G.
New York Must-See Places Tour
You cannot visit NYC without seeing the Brooklyn Bridge and it would be crazy to miss the Empire State Building... But there’s also Rockefeller Center, Statue of Liberty, the Grand Central, the Chrysler Building, the Flatiron, Wall Street, Times Square, Greenwich Village, Chinatown, and so much more. Come with me and meet Manhattan! This tour covers the most important "must-see" places in New York and more!
Brooklyn Bridge and more - Financial District Tour
The very south tip of Manhattan Island boasts some of the best and most recognizable views in New York: one can see Brooklyn Bridge, Statue of Liberty and the New York Harbor. This is the most historic area in New York - the city started here in the 17th century as a Dutch colony of New Amsterdam. This is a home to Wall Street with the world's most powerful financial institution - New York Stock Exchange. On this tour, we will walk through the history of New York and enjoy magnificent vistas
The Metropolitan Museum Highlights Tour
Indisputably one of the best museums in the world, the Metropolitan houses over two million artworks covering 5,000 years of human history! The museum is as fantastic as it can be overwhelming. This curated tour will help you make the most of your time in the museum and see the collection highlights. Join me for a stroll through the Metropolitan, filled with tales from Greek mythology, stories behind the masterpieces, and glimpses into the turbulent life of the artists.
