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New York City’s Upper East Side is an iconic neighborhood situated between 59th and 96th Streets, with Central Park to the west and the East River to the east. Today the Upper East Side remains one of the most expensive residential neighborhoods in the United States. Eloquent Fifth Avenue mansions and fabulous Madison Ave shopping continue to draw movies and television to emulate the wealth, beauty and power found in this timeless neighborhood.

Some of best-known Upper East Siders appear on Gossip Girl, but these teens are far from the first to live amongst the picturesque scenes the UES has to offer. The teens of Cruel Intentions and the Sheffield children from The Nanny called Fifth Avenue and the opulence that surrounds it home years before Blair Waldorf and Serena van der Woodsen. Before all of them, Holly Golightly and Paul Varjack called this neighborhood home in Breakfast at Tiffany’s.

Check out more of Holly and Paul’s world on the TCM Classic Film Tour. Receive your Upper East Sider credentials on the Gossip Girl Sites Tour or explore the numerous mansions and museums on the When Harry Met Seinfeld Tour.

TCM Classic Film Tour Features

For fans of Turner Classics and the golden age of film this tour is the best way to dive into the historic Upper East Side. Cruising south on Park Avenue the Met Life building towers above the neighborhood. Before it became the Met Life Building in 1991 it was the PanAm Building and is where Clint Eastwood arrived in New York by helicopter in Coogan’s Bluff.

Turning off Lexington Avenue is the apartment building of Holly Golightly and Paul Varjak (Audrey Hepburn and George Peppard), from the American classic Breakfast at Tiffany’s. Ms. Hepburn’s hairstyle, oversized cigarette holder and sunglasses are iconic symbols of the 20th Century. Most iconic is probably her little black dress, which is still a fashion necessity over 50 years after the film’s release.

Any Upper East Sider with a view of the East River doesn’t go a day without seeing the massive Queensboro Bridge. Isaac and Mary (Woody Allen and Dianne Keaton) take in a beautiful view while watching the sunrise in the classic Manhattan.

Museum Mile

Lining Fifth Avenue from 82nd to 105th Streets is perhaps the most concentrated display of culture in the world. Referred to as “Museum Mile,” there are ten museums located along this stretch, and most have been featured on TV and in the movies.

The Metropolitan Museum of Art and the Museum of the City of New York were featured in almost every episode of Gossip Girl. Blair Waldorf loved holding court on the beautiful MET steps, while her peers were attending class at Constance Billard School for Girls down the block (aka the Museum of the City of New York). The Bass/van der Woodsen wedding took place across the street at the Cooper Hewitt Design Museum. Most famous is the MET, which is often featured in beloved romantic comedies like Maid in Manhattan, Hitch, and When Harry Met Sally.

Fifth Avenue Mansions & Madison Avenue Shopping

Famous American families have spent generations on the Upper East Side. The Kennedys, the Rockefellers, the Roosevelts, the Carnegies, and the Astor’s have all left their mark on the neighborhood.  The When Harry Met Seinfeld Tour gives guests a glimpse of the mansions these families power evoked, while the Gossip Girl Sites Tour showcases the fabulous shopping of Madison Avenue.

The Valmont Mansion is where Sebastian and Kathryn (Ryan Phillippe and Sarah Michelle Gellar) develop their cruel intentions for Annette (Reese Witherspoon) in Cruel Intentions. Just down the block Big buys Carrie a splendid penthouse in the Sex and the City movie. She’s worried about the price, but he assures her “I’ve got it.”

Just off Fifth Avenue is the other location used for Constance Billard/St. Jude’s, a landmark building known as the Baker Mansion. Only a block away is the real inspiration behind The Constance Billard School for Girls, The Nightingale-Bamford School.  An elite Upper East Side school for girls, Nightingale is where Cecily von Ziegesar, the author of the Gossip Girl books on which the TV show is based, attended until her high school graduation (tuition at The Nightingale-Bamford School runs around $35,000/year).

But the Upper East Side isn’t just about NYC’s elite homes and schools, it’s also about the fabulous restaurants and shops!  The Upper East Side is home to countless unforgettable restaurants.  And high-end designer boutiques abound along Madison Avenue in the Upper East Side.

A stroll down Madison Avenue in Manhattan’s Upper East Side will bring any fan of expensive labels past some familiar names. Famous designer boutiques line the avenue; Polo/Ralph Lauren, Yves Saint Laurent, Calvin Klein, Christian Louboutin, Dolce & Gabbana, Giorgio Armani, Jimmy Choo, Oscar de la Renta Roberto Cavalli, Valentino and Vera Wang all do incredible business in this epicenter of wealth. Even the department stores are too high-end for most people; Bloomingdale’s, Henri Bendel, and Barney’s New York all cater to the lifestyle of Upper East Side residents.

Naturally, celebrities love to call the Upper East Side home. Audrey Hepburn, Bill Murray, Brooke Shields, Diana Ross, Elizabeth Taylor, Francis Ford Coppola, Frank Sinatra, Jacqueline Kennedy, and Tom Brokaw have all been “Upper East Siders” at one time or another.

* In an effort to stay current, we are constantly updating our tours with new locations and cannot guarantee the presence of locations mentioned on our site. If you have a particular interest in locations from a specific TV show or movie, please let your tour guide know and we will do our best to accommodate your request.