Holdouts: A NYC Architecture Walking Tour

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.

City: New York City

Thu 24 Apr

Other dates

You can choose the date already on the booking website

Starting at $79.00

Make a reservation

Thu 24 Apr

Starting at $79.00

Make a reservation

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What's Included

Professional guide

Additional Info

Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Travelers should have at least a moderate level of physical fitness
It is recommended to wear comfortable shoes

What To Expect

Citicorp Center

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.

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!

Chrysler Building

Stunning views of this stunning landmark are had along here.

United Nations Headquarters

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

42nd Street

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

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.

Brooks Brothers

This historic New York City institution had a holdout as a neighbor.

Diamond District

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.

Show 5 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (29)

Bouwensc

Oct 2019

This tour was an amazing way to see the city. Even though it was my first time visiting New York, I feel like I know the city even better than many lifelong New Yorkers. I’d definitely recommend this tour to anyone interested in history or understanding why New York City looks the way it does. Rob’s tour is wonderful, full of information, enlightening, and entertaining.

Response from Host

Oct 2019

Thank so much and you were awesome to take around!

Urmyy

Oct 2019

Rob puts the history together in a way that makes all of New York City logical and accessible. Streets I’ve known (or thought I did) and seen a thousand times when I used to live to in New York before I now see in a totally new light. I wish I’d known this information years ago! Brilliant!

hockey6767

Oct 2019

The tour was a fantastic experience as Robert is a very knowledgeable and engaging guide and the tour offers a unique perspective on midtown Manhattan. After the tour we will be looking with new eyes to NYC and other cities. We highly recommend this to any traveller who wants more than the mainstream tourism view on NYC.

Response from Host

Oct 2019

Thank you for the great review. As always, the people on the tour are as important as the tour itself. Thank you for letting me show you this wonderful city. Hope to see you again!