Private Flatiron Architectural Marvels Tour

  • 2-8 Hours
  • Walking Tour
  • Max Guests: 12
  • Private Tour
  • Daily

Private Flatiron Architectural Marvels Tour Details

Highlights Tour

The Flatiron District is home to some of New York City’s most architecturally fascinating buildings and spaces. On our 2-3–hour walking tour of the area, you’ll get an appreciation of the emergence of some of the most important architectural structures in the city along with a history on the rise, literally and figuratively, of skyscrapers.

We’ll make sure to stop before the district’s namesake building, the iconic, wedge-shaped Flatiron Building. Hear about the history behind the building as well as that of other nearby notable skyscrapers first to grace the New York skyline, including MetLife Building and Metropolitan Life North Building.

Enjoy a leisurely stroll around Madison Square Park as your local guide regals you with stories of this upper-echelon New York neighborhood.

Half-Day Tour

Our half-day option (4-5 hours) gives us the chance to really dig deep into the Flatiron District’s history and explore more of its architectural masterpieces.

With our extra time, we’ll delight the foodies in the group with a stop at the famed Italian market Eataly as well as the original Shake Shack. Try out Italian-, deli-, and NYC bakery-style foods and learn from your local guide how these culinary institutions made the area a hotspot for great local foods.

Full-Day Tour

Make the most out of your visit and enjoy a full day (up to 8 hours) with us sightseeing and eating with a stop at some of your guide’s favorite speakeasies!

Sip on a Prohibition cocktail or two (or three) as you hear about the emergence of city speakeasies in the 1920s and the more recent growth of speakeasy-style bars in modern-day Manhattan.

From here, your guide will have plenty of recommendations on where to eat, drink, and explore in the city.

Price Includes

Price Excludes

  • Local English-speaking guide
  • Souvenirs
  • Guide gratuity
  • Additional food & drink


Flatiron Building

You’ll discover the history and unique facets of this one-of-a-kind New York building. Your New York City tour guide will point out the intricate ornamentation and fascinating architectural challenges the designers faced during and after construction.

Union Square

You’ll have a chance to visit a park beloved by locals and known for its year-round farmers markets. Here, we’ll not only admire the surrounding 19th and 20th century buildings but also talk about where New Yorkers’ food comes from and the importance of eating local in such a densely populated globally connected metropolis.

Met Life Building

During our New York City walking tour of the Flatiron District, we’ll be admiring the midtown Manhattan skyscraper and learning about its past notable occupants and its placement among other New York landmarks as well as similar buildings built in the International style.

Metropolitan Life Insurance Tower

This National Historical Landmark is notable for its four clock faces, bells, and lighted beacons and once held the record of being the tallest building in the world until 1913.

Madison Square Park

From its pre-settlement days as a swamp to a modern-day urban oasis dominated by iconic skyscrapers, this park holds centuries of history that reveal the evolution of the city.

Gramercy Park

Your private NYC walking tour will pass by this exclusive urban retreat, the keys to which are held by only a select number of people residing in the brick townhouses and hotels surrounding the park. The area is also home to The Players Club, a private social club in an 1847 mansion that serves as a meeting space for elite actors.

Theodore Roosevelt Birthplace National Historic Site

Our NYC walking tour will be passing by the recreated boyhood home of the only U.S. President born in Manhattan! We’ll admire the handsome brownstone’s exterior details and learn about the historic collection housed within.

Community Impact

Along the way, your guide will have plenty of recommendations for enjoying New York’s local food scene, a critical part of supporting New York’s post-pandemic food industry.

Your tour includes the stories and perspectives of protestors who have long rallied for causes at historic Union Square.

Our walking tour features the Union Square farmers market, when operating, and highlights the importance of supporting local food networks and small businesses.

This tour experience highlights the arts community in New York City, including the social club for artists and arts lovers, The Players Club, a supportive meeting place for actors, writers, and industry professionals.


Walking Tour

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