The Historic Hotels of New York: Grand Architecture, Posh Style & Eccentric Guests

Opulent design and unforgettable stories

This walking tour tells the story of the famous hotels of Midtown from The Plaza and St. Regis to the Peninsula and Waldorf Astoria. Learn what the neighborhood was like before they were built and how they survived the challenges of Prohibition and beyond.

We’ll cover all kinds of hotels: transient, apartment, bachelor, Raines law, and more, but the focus will be on the lavish, post-Gilded Age hotels that set the standard for elegant design and cutting-edge technologies. Many residents settled in for months or even years. Get ready to hear their incredible stories.

Upcoming Dates:
Sunday, May 26th at 10:30 am

Book online now!

The Tour

On the walking tour, you will:

  • Hear how wealthy New Yorkers both fought and embraced grand hotels (and each other)
  • Discover how a double strand of pearls was part of a key real estate transaction
  • Understand how hotels whet the appetite of visitors for new technologies, served as exemplars for genteel behavior, and facilitated mobility by providing services usually found in the home
  • Enjoy stories of fabulous parties and eccentric hotel guests
  • Learn how the ‘apartment hotel’ was really a sleight of hand to circumvent zoning laws
  • Consider why John Jacob Astor could have regretted commissioning his face to appear in a Maxfield Parrish mural
  • Learn how reining in of sidewalk dining structures is nothing new
A walking tour in front of the Yale Club.

Key stops:

  • Plaza Hotel, the venue for Truman Capote’s Black and White Ball
  • St. Regis, where the Red Snapper got its start at the King Cole Bar
  • Barclay, one home of the ‘Hostess with the Mostes’
  • Cartier, once a mansion of a real estate tycoon
  • Peninsula, where the bar isn’t located anywhere near the entrance
  • Waldorf Astoria, from which many wanted to take a piece home

Book online now!

Amy leading a tour in front of the St. Regis.

Here’s what people are saying about the tour:

“My family and I (three generations) just did our first Bowery Boys tour, Historic Hotels with Amy, and it was STELLAR!

She really brought the places and the players to life with a little something for everyone including a lot of sharp commentary. Our group was large and diverse in terms of age and culture. And by the end of the tour, we had all bonded. A tremendous experience.

Thank you for inspiring all of this. I’m eager to take another tour soon.”

– Bowery Boys Walks guests


Person – Walking Tour: $40

Please contact us to set up a private tour!


2 hours


1.4 miles


This tour is best suited for teens and older

Your Guide:

Amy is a licensed tour guide with certification from the Guides Association of New York City. She has a BA in History, with a specialty in Urban Planning. Amy got her start giving tours at a winery in Charlottesville, VA, but has called Brooklyn home for almost 25 years and loves to visit historic hotels around the world. She contributed to the book Mad Men Carousel and presented at Mad Men: The Conference. Her favorite Manhattan yearly event is the Tartan Day Parade.

Study up for this walking tour by listening to these Bowery Boys episodes: