• Hudson Yards - The journey starts at one of the city’s latest developments, Hudson Yards and the High Line. We wander through the elegant, marble-clad mall featuring mostly high-end shops. The views of the Hudson River and the rail yards provide a perfect introduction to a historical discussion.

The Vessel and the Shed are two impressive architectural “follies” that dominate the courtyard.

From here, we enter the High Line, one of the most significant transformations in New York’s architectural history.

• The High Line - One of the city’s most successful redevelopment projects involved converting an old elevated freight rail into a park filled with native plants. We enjoy the New York City scenery from the third-story level and delve into the intriguing history of Chelsea, an early upscale neighborhood. Stunning new architecture continues to emerge along the park’s 1.4-mile stretch.
• Chelsea Market - The Godmother of food halls is constantly evolving and expanding its curated offerings. This is an ideal spot to pause for a snack.

The building was part of the system for which the “High Line” existed; freight trains passed through the buildings here for Nabisco (National Biscuit Company—“NBC” is visible on the building). It was said that for Oreo Cookies, the flour entered one side of the building and emerged as cookies on the other. Today, the building hosts dozens of specialty, international, rare, and exotic food vendors.

We allocate enough time here to sample a bite or two.

• Meatpacking District - We stroll through the atmospheric streets of old metal sheds and loading docks that now house chic establishments.
• West Village - We visit Myers of Keswick, “A traditional British store in the heart of NYC.” The British products in a converted mid-19th Century home offer one of many unique experiences. Groups are encouraged to try their sausage rolls, pork pie, scotch eggs, or Cornish pastry.

Next is Magnolia Bakery (famous from Sex and the City). Around the corner is the brownstone where Carrie Bradshaw lived (the show’s main character), one of the city’s most beautiful brownstone blocks.

We continue to McNulty’s, a century-old coffee and tea shop where the aroma of coffee grounds fills the air. A short walk around the corner leads to the apartment building from “Friends.”

A secluded church garden offers a brief respite before Bleecker Street and a series of specialty foods, including Bleecker Street Pizza, consistently ranked among the top pizza places.

• Greenwich Village - Along Bleecker Street, we’ll visit a few storefronts that together capture the unique character of this iconic block: Ottomanelli’s and Sons, a butcher shop that has been on the block for more than half a century; a Lotto Store “lounge” (the only place you can purchase lottery tickets with plastic!) where you can relax, drink coffee, and pick numbers; and the Pop Up Grocer, an Instagram-driven venue of goods curated based on the criteria: new and interesting, made responsibly, and packaged appealingly.

We walk the iconic, vibrant blocks of Greenwich Village with its famous venues, clubs, and restaurants, and some fascinating residential conversions.

The tour takes on a different tone for a moment when we visit the Chess Forum, a local institution for all things chess. Before crossing Houston Street into SoHo (for SOuth of HOuston), we stop at Leon’s Bagels, one of the city’s more unique shopfronts (approximately 50 sq. ft?).

• SoHo - Houston Street retains fascinating architectural evidence from when it was widened about 100 years ago.

The history is continuous with eras of homes, cast iron, and steel frame warehouses and factories, but the food is optional. We pass (or stop at) Dominique Ansel’s, a renowned baker and originator of the cronut, and then there’s the Ice Cream Museum on Broadway.

Here we learn the rich history of SoHo and see the more complex history of the city’s move uptown. Here we see the unmistakable role geography played in the city’s move uptown.

Within a few blocks, SoHo transitions into the tenement-rich blocks of Little Italy, and the beginning of the Lower East Side.

• Little Italy - We pass through Little Italy with the option of stopping at Ferrara’s, sometimes referred to as “Disney World for Desserts,” and/or the Cannoli King. Traditional “Little Italy” (there are a few historic Italian sections in Manhattan) now occupies the blocks of Mulberry Street above Canal and is largely restaurants and souvenir shops. The outdoor restaurant seating, elaborate signage, the booths in the street, the promoters, the foliage, and vibrant decor have transformed these sidewalks of Manhattan in a way like no other part of New York. Cars driving single file between the restaurant seating would seem like gondolas if they slowed down.
• Chinatown - We pass through the markets and street scenes of Chinatown and discuss the history of the Bowery and the tenement history of the Lower East Side. We explore the tangle of streets and engaging streetscapes that lead down a hill (and history) to the Old Five Points and Mulberry Bend, marking the end of the walking part of the tour.

From here, we catch a bus that takes us to a ferry, and a trip back to Midtown on the water where we will get to see the track of land we covered on the walking tour between the skyscrapers of Midtown Manhattan and the Financial District.

• Brookfield Place - We catch a ferry at Brookfield Place back to Midtown. Depending on the wait time for the ferry, we may have the opportunity to explore this site.

The 12-minute ferry ride back to Midtown provides a remarkable opportunity to put the day’s walk in the context of the greater city. Many of the sites from the beginning of the day will be seen now from a completely different perspective.

From Pier 79, we catch a bus to either Grand Central Terminal or Penn Station, depending on the customer’s tour option.

• All intra-city public transportation included (subway, bus, ferry)

• Food and drink
• intra-city transit (subway, bys and ferry)

This tour is ideal for suburbanites and commuters eager to discover the intriguing neighborhoods, sites, and spaces nestled between the skyscraper clusters of Midtown and the Financial District.

Participants can choose to start and finish the tour at either Grand Central or Penn Station, ensuring easy access via all regional rail transit (MetroNorth, LIRR, and NJ Transit).

Rest assured, this is indeed a history tour, with a special focus on the unique food shops and stores along the route! This “between-the-skyline” walking tour spans 3.5 miles, allowing ample time for your private group to pause, eat, and drink at select locations.

Gain insights into the city’s history and explore the iconic neighborhoods of Chelsea, Greenwich Village, SoHo, Little Italy, and Chinatown. A ferry ride back to Midtown offers a distinctive view of the path traveled from the water.

• Three modes of public transit (including a 20-minute ferry ride) are included in the price and time-length of the tour
• There is about 4 miles or more of walking on this tour

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