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As the sun’s first rays pierced the monochrome haze of the Manhattan morning, I could almost hear the crashing opener of the song Rhapsody in Blue blaring to life. From beneath the monogrammed sheets of my bed in the Carlyle hotel, I surveyed the architectural timeline of the sky, from the ornate Art Deco spires of Midtown across Central Park to the neo-Gothic gables of the Dakota apartment building. This view could launch a million big city dreams.

Having opened just in time for the great Wall Street crash of 1929, the Carlyle is a testament to the resilience of brassy New York. Glamorous yet discreet, clubby yet distinguished, it is also an ideal place to experience a bit of sophisticated time travel. Guests still dine on lobster thermidor amid the restaurant’s hand-painted Fortuny silk walls, and white-gloved elevator operators whisk visitors to gilded suites once occupied by Audrey Hepburn  and Marilyn Monroe. A well-heeled crowd sips gimlets at the Café Carlyle, and socialites and business types mix over martinis under the Ludwig Bemelman murals in the bar bearing his name.

Even in a city known for reinvention, it is hard to resist the allure of the past. The following restaurants, bars, sights and shopping spots provide the perfect itinerary for having a classic  time in what remains of old New York. 

21 Club
Appearing in more movies than any other restaurant in New York and visited by every president except George W Bush, this former speakeasy is still a go-to for power lunches and special occasion dinners. Get a tour of the wine cellar, which is hidden behind a two-and-a-half-ton door and opened by inserting a meat skewer through a crack in the wall. It has housed the wine collections of everyone from Elizabeth Taylor to Sammy Davis Junior. While many things remain the same -- like the legendary burger -- there is a faint nod to the future with a buzzy new lounge area. Jackets are required.  

The Palm Court
Ernest Hemingway once told F Scott Fitzgerald to give his liver to Princeton and his heart to the Plaza. He must have taken that advice to heart, as he set scenes from his most famous novel, The Great Gatsby, at the hotel’s Palm Court. Make like his characters Nick and Jordan during the legendary afternoon tea of petit fours, truffled quail egg salad and caviar, under the newly-restored 1,800sqfoot stained glass ceiling.

La Grenouille
La Grenouille is one of New York’s last great bastions of classical French cuisine: the Dover sole is still filleted tableside, desserts arrive via silver carts, and jackets are required at dinner. The ornate damask and glittering crystal in the dining rooms is matched only by the heirloom diamonds adorning its patrician diners (many of them purchased across the street at Cartier) and by the elaborate floral arrangements still arranged each Monday by the restaurant’s owner. 

Lexington Bar and Books
Puffing a stogie at the mahogany bar in this clubby watering hole will take you back to a time well before Bloomberg banned smoking, when gentlemen knew how to offer a lady a light (its designation as a cigar bar exempts it from the city’s smoking ban). But you will have to dress like a gentleman (or lady) to score a leather club chair — the front door is locked and only the appropriately attired get buzzed in.

The Paris Theatre
This luxe Art Moderne theatre around the corner from the Plaza hotel has long been a centre for foreign cinema in New York. Marlene Dietrich cut the ribbon when the art house opened in 1948, and the films shown have at times been so controversial they have inspired court cases; one decency case over a Rossellini and Fellini film went all the way to the Supreme Court. Though today’s screenings hew towards standard art-house fare, the experience of seeing a movie here between the blue velvet walls is pure New York romance.

King Cole Bar
Marilyn Monroe, Joe DiMaggio, John Lennon, Salvador Dali. New York's best and brightest have all pulled up plush stools beneath the famous Maxfield Parrish mural that lines this classic bar in the St Regis Hotel. No matter the time of day, those in the know order a Bloody Mary, invented here by bartender Fernand Petiot in 1934. Have a few and then ask the bartender to tell you the secret of the King Cole mural.

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