A Half Day Walk Between the Skyscraper Clusters of Manhattan

Meet at the clock in Grand Central. This meeting point is convenient to MetroNorth and LIRR travelers.

The excursion begins at one of the city's newest developments, Hudson Yards and the High Line. We stroll a bit of the elegant, marble-clad mall of mostly high end shops. Views of the Hudson River and the rail yards are a great segue for a history talk. The Vessel and the Shed are two grand works of architectural "folly" that dominate the courtyard. From here we enter the High Line and one of the greatest transformations in New York's built environment history.

One of the city's most successful redevelopment projects was turning an old elevated freight rail into a park of native flora. We take in the scenery of New York City from the third story level and learn the fascinating history of Chelsea, an early upscale neighborhood. Stunning new architecture continues to rise along the park's 1.4 mile length.

The Godmother of food halls is constantly updating and expanding its curated offerings. This is a perfect place to break for a snack. The building itself was part of the system for which the "high Line" existed; trains for freight went through the buildings themselves, here, for Nabisco (National Biscuit Company--"NBC" can be seen on the building). It was said for Oreo Cookies the flour came in one side of the building and came out the other as cookies. Today the building houses dozens of specialty, international, rare and exotic food purveyors. We allow enough time here to sample a bite or two.

We walk through the atmospheric streets of old metal sheds and loading docks that now house chic establishments.

We stop at Myers of Keswick, "A traditional British store in the heart of NYC." The British products in a converted mid-19th Century home is 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 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 smell of coffee grounds permeates. A short walk around the corner is the apartment building from "Friends." A cloistered church garden provides a short respite before Bleecker Street and a string of specialty foods, including Bleecker Street Pizza, among the consistently top-rated pizza places.

Along Bleecker Street we'll visit a few store fronts that together capture the unique character of this iconic block: Ottomanelli's and Sons, a butcher shop that has been more than half a century on the block; a Lotto Store "lounge" (the only place you can purchase lottery tickets with plastic!) where you can hang out, drink coffee, and pick numbers; and the Pop Up Grocer, an Instagram-driven venue of goods curated on the criteria: new and interesting, made responsibly, and packaged appealingly. We walk the iconic awning-clad, vibrant blocks of Greenwich Village with its famous venues, clubs and restaurants, and some fascinating residential conversions. The tour takes on a different attitude for a moment when we pop into 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, and one of the city's more unique shopfronts (approximately 50 sq. ft?).

Houston Street retains fascinating architectural evidence from when it was widened about 100 years ago. The history is non-stop with eras of homes, cast iron and steel frame warehouses and factoires, but the food is optional. We pass (or stop at) Dominique Ansel's, 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.

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 Manhttan) now occupies the blocks of Mulberrry 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.

We pass through the markets and street scenes of Chinatown and talk about 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, and 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 Distrtict.

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.

Meet at the clock in Grand Central. This meeting point is convenient to MetroNorth and LIRR travelers.