Even though it tends to be a bit touristy, I happen to love Rockefeller Center. It's art deco design has always intrigued me (interior and exterior) and stepping off Fifth or Sixth Avenues into Rockefeller Center’s ‘city-in-a-city’ transports you to a different era. It’s a massive complex that spans 22 acres, which is a lot of land for NYC standards. So what was there before it was constructed 90 years ago?

For me, The Plaza Hotel on Fifth Avenue and 59th Street falls into that ‘timeless, iconic New York institutions’ category. The cornerstone of Central Park’s southeast corner—it’s the first thing you see as you leave the Park, a beacon of history, architecture and of course, opulence.

But did you know that today’s Plaza Hotel is the second rendition?

Years ago, while sitting at one of my favorite Upper East Side bars, the Third Avenue Ale House (located on Third Avenue and 92nd Street), I noticed some interesting framed maps and advertisements on the wall. Upon closer inspection, I noticed they were images of a lost brewery, the Jacob Ruppert Brewery, which happened to be across the street where the condominium complex Ruppert Towers now stands!

New York City is famous for a wide variety of things like pizza, Katz’s Deli, New Year’s Eve, bagels, The Bronx Bombers, Amazin’ Mets, and of course… The Marathon. The New York City Marathon is certainly far from the oldest—Boston is clocking in at 127 years old this year—but it is certainly the best known and one of the largest with upwards of 55,000 participants.

One of my favorite Upper West Side architectural marvels—aside from The Ansonia—is The Apthorp which takes up the full block between Broadway, West End Avenue, and West 78th and 79th Streets. The Apthorp isn’t just a clever developer’s idea of a fancy name—like we see so often currently. It is a nod to Charles Apthorp Ward, who owned a 300-acre farm on the site in the early development of the neighborhood. 

When I moved to New York City in the summer of 2000, Columbus Circle was a massive construction zone. My first apartment was on the Upper West Side, so I passed through the area quite often. When the Time Warner Center finally opened in 2004, I was far from impressed. I had moved to Alphabet City and was embracing the gritty New York of old. The new, shiny skyscrapers full of luxury retail and fancy restaurants defied all of that.

There’s a building on a random block on the Upper West Side that you could walk by a million times and not really notice. From ground level, it appears to be just like any other full-service co-op building, but if you happen to glance up at the facade you’d be amazed.

Tudor City is a small U-shaped neighborhood that is only accessible from either 41st or 43rd streets and is elevated over First Avenue. Across from it on First Avenue sits the United Nations headquarters. One of the elements that fascinated me and pushed me to study Tudor City was when I noticed that all of the windows facing the East River were very tiny. When developing Tudor City, why wouldn’t they have massive windows looking out over the river and into Queens?

Many of us are familiar with Fifth Avenue between 42nd and 57th Streets. We typically don’t think much of it, as today it's lined with skyscrapers housing corporate offices with high-end retail on the ground floor. It has always intrigued me because prior to the 1920's, this is where you could find many elaborate mansions of the city’s elite.

The Stevens-Whitney Mansion is a forgotten relic that doesn't often get mentioned due to its neighbor, The Vanderbilt Mansion.

One of my all time favorite buildings in all of New York City is the Ansonia on the Upper West Side. Located on the west side of Broadway and 73rd Street. It has quite a presence—architecturally and historically—that really can’t be overlooked. Just like any older building, it has a few stories to tell.

One of the most architecturally stunning blocks in Manhattan is 93rd Street between Park and Madison Avenues. It’s a quiet street, lined with cherry blossom trees in a downward curve toward Central Park, visible just a block away. Still surviving on the quaint street are three beautiful mansions that once were home to New York’s elite. The George Fischer Baker House, Loews Mansion and Virginia Vanderbilt Mansion are all clustered together. All three families were friends and chose to build on the same block. Today, let’s learn about the Vanderbilt Mansion, as it recently sold for an astronomical figure off-market.

Come with me as I take you on a tour of some of the Upper East Side's most famous landmarks and my favorite restaurants and bars. Look out for the famous steps of the Metropolitan Museum of Art, the scenic greenery in Central Park, and a classy piano bar that just might serve the best martini in the city.

The Schwab House is a large, well-known co-op on the Upper West Side. It has a rich history - both literally and figuratively! Its namesake, Charles Schwab, was a captain of industry at the time he built his opulent mansion here.

The second iteration of the Waldorf Astoria Hotel (or perhaps third or fourth, depending on how you look at it!) opened in 1931. At the time it was the largest and tallest hotel in the world. It spanned the entire block and stood 47 stories high. The hotel was also the first to have many modern amenities - electricity on every floor, ensuite bathrooms in every room, and 24-hour room service!

As we celebrate the 4th of July and Americana, what better venue to showcase than the Waldorf Astoria Hotel? Family feuds, capitalism, and old money…this building’s got it all!

The original Waldorf Astoria Hotel was not one hotel but two.

Did you ever think you could own the oldest single-family home in Manhattan? Me either.

I love going to The Met… I’m there twice a month at least. I also live in the neighborhood so it isn’t too much of an ordeal to walk over. One thing that’s always caught my eye, was this gorgeous mansion directly across the street. I always thought it was a private school, like so many of the other retired mansions in the area, but it’s not!