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Fifth Avenue Walk and Live Jazz
The best that New York has to offer: amazing history, dizzying landmarks, and sounds of jazz! Join me for a walk along Fifth Ave - the name associated with wealth, glitz, and glamor. Fifth Ave, one of the best-known streets in the world, used to be lined with the finest homes of the wealthiest people -- a place of ambition, intrigue, scandal, and the most spectacular balls ever given. Along the walk, we'll see famous sites, learn their stories and finish the evening with jazz and cocktails.
Meeting Point
In front of the Plaza Hotel (5th Avenue between 58th and 59th Streets)
In front of the Plaza Hotel
17:00 PM Meeting and introductions
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17:00-17:15 A bit of NYC history, geography, and importance of Fifth Avenue
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Please, note that this is just a sample itinerary. We might choose to stop longer at some locations and skip some other places depending on your interests. Also, the start time might vary depending on the time of the year and a show start time.
17:20-19:00 Fifth Avenue Stroll
- The Plaza Hotel
One of America’s finest and most celebrated luxury hotels, it has the distinction of being the one and only. When it opened it was hailed the “greatest hotel in the world.”
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- Pulitzer Fountain
The exquisite female figure atop the fountain in front of the Plaza Hotel is an allegorical depiction of Pomona, the Roman goddess of fruitful abundance. The model for Pomona was Ms. Audrey Munson who, owning to her flawless beauty, was known as the American Venus. Her story is as fascinating as it is tragic.
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- Tiffany & Co.
The world’s most iconic jewelry store is home to a little blue box with the white satin ribbon tied around it - the Tiffany Blue Box - one of the most recognizable and desired retail containers in history. “Breakfast at Tiffany’s,” a 1961 movie based on a novella by Truman Capote, added a soft glow of romance to the store’s dazzling reputation.
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- Trump Tower
A 58-floor skyscraper serves as the headquarters for the Trump Organization and houses the penthouse residence of businessman, real estate developer, and former U.S. President Donald Trump, who developed the building and named it after himself.
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- St. Patrick's Cathedral
The spectacular Gothic Revival St. Patrick Cathedral, named after the patron saint of the Irish, is the largest Catholic cathedral in North America. Designed by New York's own James Renwick Jr., it took almost 20 years to build.
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- Rockefeller Center
The Rockefeller Center is a complex of 19 interconnected buildings — 14 of them being the original Art Deco office buildings from the 1930s. The focal point of the complex is 30 Rockefeller Plaza (formerly the GE and RCA building), a stunning Art Deco masterpiece. Narrow, simple, and elegant, it appears taller than its actual height and is crowned by a three-tiered observation deck.
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- The St. Regis Hotel, St. Thomas Church, Cartier Building . . . and more
There are many landmarks on the way and each has a story to tell...
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19:00-19:30 Walking to a jazz club
We are going to leave Fifth Avenue and walk over to the club, most likely we will go through Times Square
19:30 - 20:30 Live jazz
Nothing says New York like live jazz. We will come to a club where we'll listen to some great music over a drink or dinner. You are welcome to stay there as long as you like.
Ending Point
Jazz club
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Inclusions & Exclusions
Friendly Licensed NYC Guide
Suggestions for your future explorations of New York City
Information on jazz venues and speakeasies
Dinner and/or drinks
Cover charge
Tour Important Information
- It's a very small group tour; in fact, it should not feel like a traditional tour but more like a walk with a group of friends.
- The walking portion of the tour takes about 2-2.5 hours. The rest of the time is music and it's up to you how long you'd like to stay. Jazz shows venues may vary depending on the day. I will adjust the tour route accordingly to make it most interesting.
- The itinerary is a sample; the time we will spend in front of POIs is approximate and will depend on your interests.
- Please, contact me before booking so that I can make sure there are live jazz shows that day and make reservations.
- Please, let me know if you'd be interested in having dinner at a jazz club or just drinks.
Important message from the guide
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
New York Tour 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.
(3 reviews)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.
(3 reviews)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.
(3 reviews)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!
