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Holdouts: A NYC Architecture Walking Tour

36 Reviews 4.97 out of 5 stars Based on 36 reviews collected by Cool NYC and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. New York City, USA
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from $59 per person

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Holdouts: A NYC Architecture Walking Tour Image 1
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Don't miss out!
On average, this is booked 20 (0) days in advance.
2 to 3 hours (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

This 2.5 hour walking tour around the Midtown Manhattan shows-and-tells the fascinating stories of holdouts—the intriguing side effect of Manhattan's pressure cooker real estate industry: when a property owner (or lease holder) refused to sell to a developer, forced them to rework their plans, and forever changed the city streetscape. Stories, like the elderly lady who never knew any other home; or the poker player-like landlord who overplayed his hand; or the restauranteur whose long term lease (justifiably) demanded budget-busting sums, all add a human dimension to these transactional anomalies. And personal stories that were otherwise lost, are awesomely amplified by the everlasting impression left behind: seemingly ill-planned entrances for skyscrapers, odd shaped buildings, 20-story tall notches in office towers, are just some of the 16 examples of holdouts we'll see.

This tour is based on the book, Holdouts! By Alpern and Durst.

What's Included

  • Professional guide
  • Gratuities
See 1 more

Meeting Location

Meeting point

875 3rd Avenue
New York, NY 10022, USA

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

22 East 54th Street
New York, NY 10022, USA

Papillion Restaurant

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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TPR Holdings

We start in lower lobby of this distinctive building where we'll lay the groundwork for the tour, where we'll go and what we'll see. The building itself is the result of holdouts, and our first subject.
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15 minutes Admission Ticket Free

Lipstick Building (pass by)

A fascinating ego building
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Citicorp Center (pass by)

Not a holdout, but a fascinating story is associated with the construction of this building, whose main pillar supports are not in the corners, but in the middle of the side.
Read more

Wollensky's Grill

An old buggy whip factory, and a holdout.
Read more

5 minutes Admission Ticket Free

Amster Yard

If this oases is open at the time of the tour, we stop in for a moment. A time capsule where histories clash and the city meets the suburbs - - a much earlier one!
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5 minutes Admission Ticket Free

Sparks Steak House

This notorious site of a mob hit is next door to an interesting holdout.
Read more

5 minutes Admission Ticket Free

Chrysler Building (pass by)

Stunning views of this stunning landmark are had along here.
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United Nations Headquarters (pass by)

We view the Secretariet Building down the block as we continue to pass and discuss holdouts and how they've influenced the streetscapes today.
Read more

42nd Street

We end our downtown part of the walk at 42nd Street, where a single holdout survived history.
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5 minutes Admission Ticket Free

Grand Central Terminal

As we make our way to the west side and the uptown portion of the tour we will pass through Grand Central. While not associated with a any holdouts, a mini-tour of this iconic landmark is very possible.
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5 minutes Admission Ticket Free

One Vanderbilt (pass by)

This city-in-a-building was still under construction at this writing.
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Brooks Brothers

This historic New York City institution had a holdout as a neighbor.
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5 minutes Admission Ticket Free

Bank of America Tower (pass by)

We view this crystal shard-iceberg mashup of a building from the side
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The Roosevelt Hotel (pass by)

We pass by this sole survivor of Terminal City, from a time before air travel when Grand Central linked to three hotels to receive cross-country travelers.We continue our tour passing fascinating ways holdouts have changed the look of the city.
Read more

Diamond District (pass by)

Worth noting the block where $440 million in diamonds are traded daily. The entrance a block to the north as we cross Fifth Avenue is flanked by 12' diamond sculptures.
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Rockefeller Center

Rockefeller Center's rich history includes a number of interesting, thought provoking holdouts.
Read more

10 minutes Admission Ticket Free

Papillon Bistro & Bar

We end the tour here, one of the most compelling examples of a holdout, and is more appropriately a hold-IN. Here a restaurant proprietor negotiated additional square footage to expand his restaurant into the future skyscraper. You can enter the skyscraper today and stand within the walls of a 19th century brownstone.
Read more

5 minutes Admission Ticket Free

Show 16 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Service animals allowed
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • It is recommended to wear comfortable shoes

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Holdouts: A NYC Architecture Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-44899P6

Traveler Photos

Reviews

4.97
36 reviews

Average 4.97 out of 5 stars based on 36 traveler reviews collected by Cool NYC and partner sites such as Cool Destinations and TripAdvisor

5 stars
35
4 stars
1
3 stars
0
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 20 (0) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool NYC customers.

Filter by:

Q: What is the cancellation policy for the Holdouts: A NYC Architecture Walking Tour?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EST).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Professional guide.
The following is NOT included:
  • Gratuities.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Holdouts: A NYC Architecture Walking Tour is as follows:

  • Wheelchair accessible
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Holdouts: A NYC Architecture Walking Tour will be included in your confirmation email from Cool NYC. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Professional guide
  • Gratuities

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • It is recommended to wear comfortable shoes
  • This tour/activity will have a maximum of 5 travelers

Report Product Issue

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