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Fifth Avenue Walk and Live Jazz

Pomona of the Pulitzer Fountain

The Pulitzer Fountain

The Plaza and General William Tecumseh Sherman Monument

The Plaza's castle-like roof

Rockefeller Center

Atlas Statue at the Rockefeller Center

Rockefeller Center Prometheus

The British Empire Building at the Rockefeller Center

St. Patrick's Cathedral

Tiffany Lamp

Tiffany's iconic blue box sculpture

The Rockefeller Center during holidays

Cartier dressed for holidays

Van Cleef & Arpels

Bergdorf Goodman holiday windows

Saks Fifth Avenue windows

Trump Tower

In front of the Plaza

The St. Regis Hotel

The Cartier Building

Fifth Avenue view

Fifth Avenue Walk and Live Jazz

Art, Culture, & Historical

Joined 2021

Iren G.

5.00 / 5

(4 reviews)

Identity Verified

Interview-Based Quality Checks

New York

English

3 hrs 30 mins

Private tour (only you and Iren G.)

Up to 5 people

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.

Itinerary

This itinerary can be customized to meet your needs and preferences. Send me a message with your requests!

05:00 PM

Meeting Point

In front of the Plaza Hotel (5th Avenue between 58th and 59th Streets)

05:00 PM

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.

05:20 PM

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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07:00 PM

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

07:30 PM

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

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

What‘s included

Friendly Licensed NYC Guide

Suggestions for your future explorations of New York City

Information on jazz venues and speakeasies

What‘s not included

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 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

Iren G.

5.00 / 5

(4 reviews)

Identity Verified

Interview-Based Quality Checks

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

Cathy B.

5 / 5

May 30, 2025

New York Must-See Places Tour

Fifth Avenue Walk and Live Jazz

Itinerary

Want to personalize this tour?

Inclusions & Exclusions

Tour Important Information

Important message from the supplier

Cancellation Policy

About Tour Guide Iren G.

Reviews