Long after John F. Kennedy and Marilyn Monroe’s top-secret trysts, The Carlyle on New York’s Upper East Side remains one of the world’s most glamorous hotels.

Legend has it that after singing Happy Birthday, Mr President at John F. Kennedy’s birthday bash on May 19, 1962, Marilyn Monroe quietly slipped out of Madison Square Garden and made her way to The Carlyle. To avoid the paparazzi, she sneaked into the hotel through its East 77th Street service entrance and took the elevator to the 34th floor. Kennedy arrived soon after.

There’s so much mystery surrounding the events of that night it’s impossible to know if the story is true. There’s little doubt, however, that the president’s apartment – which sprawled over the 34th and 35th floors of the hotel – was where Monroe and Kennedy met for many secret rendezvous. In fact, The Carlyle was Kennedy’s New York residence for the last 10 years of his life. And after JFK was assassinated, Jackie Kennedy moved into the hotel with her children for 10 months, although she stayed on the 31st floor.

Of all the features The Carlyle offers, privacy is the most luxurious. It’s no wonder so many of the rich and famous have stayed here throughout its history – from the Kennedy kids who played in the lobby on rainy days back in the 1960s, to Prince William and Kate Middleton, who checked in last year during their first trip to New York together. Of course, where they stayed in the hotel remains a closely guarded secret.

A stroll through the Art Deco hotel is the best way to get a feel for its history. Have a drink at Bemelmans Bar, named after children’s book author and illustrator Ludwig Bemelmans, who painted the room’s murals. Or head to Café Carlyle, where stars such as Paul McCartney and Cyndi Lauper have performed – and where Woody Allen plays clarinet with the Eddy Davis New Orleans Jazz Band most Monday nights.

Upstairs, the two-bedroom Royal Suite 2209 – with high ceilings, vintage chandeliers and velvet furnishings – was where Princess Diana used to stay. Or perhaps check into our favourite suite: the Carlyle 1801. Decorated by interior designer J. Cameron Barnett and with partial views of Central Park, it’s all Art Deco and mirrors – the perfect way to indulge in some old Hollywood glamour.

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