Viator · group up to 5 pax

Holdouts: A NYC Architecture Walking Tour

4.9(35)New York City1 hour
VIATOR4.9(16)TRIPADVISOR4.8(19)

Description

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.

Tour Options

Start Times

Itinerary

15 min

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.

Pass by

A fascinating ego building

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.

5 min

An old buggy whip factory, and a holdout.

5 min

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!

5 min

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

Pass by

Stunning views of this stunning landmark are had along here.

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.

5 min

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

5 min

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.

Pass by

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

5 min

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

Pass by

We view this crystal shard-iceberg mashup of a building from the side

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.

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.

10 min

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

5 min

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.

Highlights

Professional guide

What's included

Included
Professional guide
Not included
Gratuities

Traveller Ratings

4.9
35 reviews
5
33
4
1
3
0
2
0
1
1

Important Information

  • 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

Reviews(35)

1
127mariannb
May 4, 2026
Great tour for NYC history/architecture!

We love history and architecture and selected this tour because it sounded a bit quirky from typical tours. It was fantastic! Rob is so enthusiastic and knowledgeble. We really enjoyed this tour- we kept pointing to other possible "holdouts" during the rest of our time in New York! We'll definitely take one of Rob's other tours next time we're in the city!

Operator response

Thank you for the great review! I hope to see you again!

J
James_S
April 24, 2026
Very educational tour and the guide was happy to modify to address our interests.

This is a walking tour so be aware. That said I am elderly and the guide was happy to find sitting spots during the tour. Very knowledgeable guid who combined architecture with general history of the city. Plenty of old pictures and graphs. Also, we were interested in churches so the tour was modified to spend more time there.

Operator response

Thank you for the great review, I truly appreciate it and hope to see you again!

P
patricia_t
April 20, 2026
See NYC from then to now!

Tour guide was full of interesting details about the development of NYC, the buildings, the Open Spaces, the Underground alleyways and galleries- a truly delightful experience.

Operator response

Thank you!!! I hope to see you again!

S
Serena_F
February 14, 2026
Outstanding Tour and Guide

We really enjoyed the tour! Our guide was fantastic— extremely knowledgeable and friendly and very attentive to what the group might be interested in or need, etc. It’s a lot of walking (3 hours) but very enjoyable!

Operator response

Thanks so much for the great review and I hope to see you again!

S
Susanne_A
September 26, 2025
Nice Tour and Grab your Tennis Shoes and get ready to move fast.

Nice tour, a bit rushed, no time for photos or question, but interesting none the less. I learned about the Privately Owned Public Places which was helpful information that I shared with a young traveler visiting New York after me. My only suggestion would be to move quicker through the beginning of the tour where we sat and looked a printer copy of buildings. We could have done that during the tour and allowed for photo, questions, and a slower pace to enjoy the city scape.

Operator response

Thank you for the review. and this is a legitimate criticism to a point, and I'm sorry your experience wasn't better. I struggle with how much time to spend at the beginning putting the tour in context and discussing the city's development. I try to be responsive to guests, could and would have slowed the pace, and definitely stopped to take pictures if I had any indication. This was a tour on holdouts, and we do pass some amazing spaces going from one holdout to another. My groups are very small and everyone is different, and I try to match the pace with what I think people want. Of course I don't want my guests to feel rushed, I'm sorry I misjudged things.

R
robertj_m
August 24, 2025
5 Stars Skycraper Tour

Excellent explanation of the NYC history of skyscrapers & how they began to flourish in the skyscraper race. Our guide, Rob, was outstanding! Answered questions throughly & new intricate ideas about city planning, building & impact on local housing. Intriguing view of NYC skyline.I highly recommend this tour! 5 stars

Operator response

Thank you so much for the great review! It was a pleasure taking you around, I hope the rest of your trip was awesome, and I hope to see you again!

S
Stephen_B
May 24, 2025
Very informative and interesting

Robert was amazing. Packed with so much contextual knowledge! Had a great pace and answered all of our questions enthusiastically.

Operator response

Thank you! It was great taking you around and I hope to see you again. You guys were awesome.

8
866shmuelh
December 24, 2024
Fantastic tour by a fabulous tour guide- thank you!

Rob is a fountain of enthusiasm and information- he knows more about NYC architecture and history than anyone I have ever met- and he loves constantly reading and learning. Anyone doing this tour will be rewarded and realize just how lucky they are- highly recommended!

Operator response

Thank you for the review! I hope to see you again, Rob

M
MaryD151
December 15, 2024
Unique angle on NYC, guided by a master

Who knew? Maybe you’ve seen a small building crammed between two skyscrapers and wondered what went wrong. In fact, these “ holdout” owners and buildings have unique histories and often, powerful purposes. For example, have you ever heard of a “lightsaver?” Not the candy, a short building that doesn’t block the sunlight of the apartments on the side of a very tall structure. Or the charm and pride of small businesses built by families who don’t want to give them up. The stories are many and all interesting. Rob Amell’s meticulous research has uncovered their histories and secrets, and the trip is worth it! This tour is not for first time visitors to our City but for those from NYC and away who love the uniqueness of our town. Rob is a master and he should write books about is work. His tours are 3 hours but zoom by. Highly recommend.

Operator response

Thank you so much for the awesome review!!!

S
Sifredo_A
December 11, 2024
Unique

Great! Very knowledgeable. We were the I ly ones so got an extra hour. Highly recomend. Got to learn a few secret spots to enjoy later on.

Operator response

Thnk you so much for the review, I hope to see you again!