Upper East Side Tour: Culture and Architecture of the Gilded Age

From Beaux-Arts to billionaires, dive into Fifth Avenue's architectural evolution
From US$337 privately
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Tour Details
3 hours
Product Type
  • The Plaza Hotel
  • The Metropolitan Club
  • Roosevelt House
  • Fletcher-Sinclair mansion
Photos & Highlights
  • Walk where titans tread. Uncover the stories of wealth, power, and ambition hidden within Beaux-Arts facades. This isn’t just another walking tour — it's a time travel ticket to the Gilded Age.
  • Go beyond the luxury shops and doormen to gain a deeper understanding of the city's evolution. This tour is for the curious explorer who wants to experience New York like never before.
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Tour Description
Step out onto Fifth Avenue, not as a hurried tourist, but as a member of New York City’s elite. Unlock the secrets that are held inside New York City's glamorous architecture, letting your expert guide transport you back to the city’s dazzling Gilded Age. Are you ready to learn about the lives lived inside these stunning buildings?
  • Begin at the iconic Plaza Hotel, a French Renaissance château where presidents and stars once mingled. Catch the sunlight as it glints off the marble base and white brick facade, while intricate details on the mansard roof captivate. Let our expert guide paint a vivid picture of lavish parties and whispered secrets within its hallowed walls.
  • Move to the triumphal arches of Grand Army Plaza, a Beaux-Arts masterpiece frozen in time. Imagine carriages rolling down its avenues, carrying the elite to exclusive clubs and private schools. Peek through wrought-iron gates at the exclusive clubs that defined the Upper East Side's elite, including the Metropolitan Club, the Browning School, the Links Club, and more.
  • Walk in the footsteps of the Vanderbilts, Buchanans, and Roosevelts. Palatial mansions stand as testaments to their power and influence. It won’t be difficult to imagine the Gilded Age opulence within, reflected in the ornate stonework and grand Beaux-Arts and Renaissance revival styles.
  • Unravel the mysteries of the Frick Mansion, now a renowned art museum. Immerse yourself in the stories of Henry Clay Frick, the steel magnate who transformed this opulent residence into a treasure trove of artistic masterpieces. Imagine the life he led, surrounded by priceless paintings and sculptures.
  • Stop at the Ukrainian Institute of America, a publicly accessible gem showcasing eclectic French Renaissance architecture. Let your imagination soar as you hear tales of its past residents, businessmen who built empires and left their mark on the city's cultural landscape.
Your exclusive invitation into the heart of New York's most glamorous avenue awaits. Join us to unlock the secrets hidden within its magnificent architecture, leaving with a newfound appreciation for the grandeur and intrigue of the Gilded Age.

  • You want to trade Instagram filters for real-life opulence, transporting yourself to the Gilded Age complete with stories of the Vanderbilts, Buchanans, and enough excess to make Jay Gatsby blush.
  • You’d like to get your fix of Beaux-Arts and Renaissance beauty with expert commentary that adds context around the history and hidden symbols along the avenue.
  • You’re keen to unravel the city's DNA through its buildings, decoding its architecture and understanding how it reflects New York's evolution from Dutch settlers to Wall Street titans.
  • You’re interested in learning about the human ambition, triumphs, and struggles that shaped the avenue. 
Can we customize what we see on this tour? 
The guide has selected these locations along the route because of their importance and value in the story they tell of these neighborhoods. All of our tours are meant to be conversational and on occasion, guides will choose to visit some landmarks vs. others based on clients' interests and how much walking they are up for. 

Will we be able to enter the mansions?
Most of the mansions are inhabited by New Yorkers while some are repurposed as museums and institutions. We may be able to view one or two from the lobby/entrance. The private social clubs are restricted to members only.

Can we do this tour without walking? 
This is a walking-only tour. Please expect to cover 1.6 miles more or less, have comfortable shoes on and prepare for the weather. 

Book with confidence — see Context's flexible cancellation policy here.

Where You'll Start
(4.8) 42 Reviews

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Sam was great. He was very knowledgable and flexible. We took a trip to the JP Morgan library and museum which was not on the tour. I enjoyed looking at the architecture, stories about the polish consulate, and having a beer at a local 'pub'. Overall, a really good day! Lori Potter
Brad was excellent! We have walked by these buildings so many times with little or no history of them before we did this tour! Ty Brad!
As native New Yorkers it was fun to learn about a piece of the city we didn’t know much about and Michele the guide was a pleasure