Historical Walking Tour of NYC Hotels with Bowery Boys
Difficulty
easy
Duration
2 hours
Fitness Level
Casual walking; suitable for most fitness levels
Overview
Discover New York City's legendary hotels on a fascinating 2-hour walk with Bowery Boys. Uncover stories of glamour, eccentric guests, and historic architecture that shaped Midtown’s vibrant past.
The Historic Hotels of New York City
2 hours • 1.4 miles • Ages 16+
Select participants and date
Adventure Photos
About This Adventure
Embark on a captivating 2-hour walking tour through Midtown's iconic hotels, from The Plaza to the Waldorf Astoria. Discover the rich history, eccentric guests, and lavish parties that defined New York's grand hospitality. Uncover fascinating stories of architecture, technology, and the vibrant culture that shaped these legendary landmarks.
Grand Architecture, Posh Style & Eccentric Guests
(Best suited for adults and teenagers that have a strong interest in architecture and New York history.)
Duration
2 hours, 1.4 miles (We will send the meeting place when you sign up)
Overview
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.
The Tour:
On the walking tour, you will:
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Hear how wealthy New Yorkers both fought and embraced grand hotels (and each other)
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Discover how a double strand of pearls was part of a key real estate transaction
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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
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Enjoy stories of fabulous parties and eccentric hotel guests
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Learn how the ‘apartment hotel’ was really a sleight of hand to circumvent zoning laws
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Consider why John Jacob Astor could have regretted commissioning his face to appear in a Maxfield Parrish mural
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Learn how reining in of sidewalk dining structures is nothing new
Key stops:
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Plaza Hotel, the venue for Truman Capote’s Black and White Ball
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St. Regis, where the Red Snapper got its start at the King Cole Bar
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Barclay, one home of the ‘Hostess with the Mostes’ Cartier, once a mansion of a real estate tycoon
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Peninsula, where the bar isn’t located anywhere near the entrance
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Waldorf Astoria, from which many wanted to take a piece home
Please Note
The walking tour runs rain or shine — dress for the weather!
Private Group: Please contact us for pricing and availability
Adventure Tips
Start early in the day
To avoid crowds and enjoy a more personalized experience, join the tour in the morning.
Wear comfortable shoes
Since the tour covers a fair amount of ground, comfortable footwear is recommended.
Bring a notebook
Capture interesting stories or details you want to remember about New York’s hotel history.
Check the weather forecast
Dress appropriately for the weather, as parts of the tour are outdoors.
Local Insights
Wildlife
- Pigeons
- Squirrels
History
Many of these hotels played pivotal roles during major historical events, from Prohibition to the Jazz Age, shaping New York’s social scene.
Conservation
The hotels and tour operators prioritize sustainability by promoting walking and supporting local businesses.
Select participants and date
Adventure Hotspots in New York City
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Essential for exploring Midtown’s historic streets on foot.
Weather-appropriate clothing
Stay comfortable in weather conditions, whether sunny, rainy, or cold.
spring;summer;fall,winter specific
Camera or smartphone
Capture memorable moments and iconic sights along the way.
Notebook and pen
Jot down stories or details that interest you most.