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The Great Gatsby Long Island locations: From Manhattan to the Hamptons – discovering F Scott Fitzgerald’s inspiration

Simon Calder’s Travel

“Nothing unimportant happens at The Plaza”, it was once said of New York’s dazzling Gilded Age hotel fringing Central Park. Who uttered this bold statement remains a mystery, but many like to believe it was F Scott Fitzgerald, author of The Great Gatsby and Plaza regular along with his wife Zelda, in the roaring 1920s. A lavish suite here is also where one of the novel’s key dramatic scenes takes place. From my white-clothed table next to a tall potted palm, I glance over at the curved bar opposite. I can easily picture the party-hungry pair perched on high stools, chatting and laughing, wafting around cigarettes in holders and chugging back cocktail after cocktail.

My daydreams take place while I’m indulging in a Central Park afternoon tea at the hotel’s legendary Palm Court. Sipping champagne beneath the room’s ornate Victorian glass skylight, I must confess to feeling quite important. Even the tiny cucumber sandwiches are a major event – dainty bite-sized morsels with lemon zest and mint labneh – and the bizarre-sounding egg custard and jam combo a pleasant surprise.

The opulent Palm Court at New York’s Plaza hotel

The opulent Palm Court at New York’s Plaza hotel (The Plaza)

Ahead of The Great Gatsby‘s 100th anniversary in 2025, I was at the start of a whistlestop weekend trip to discover the real-life setting that inspired the novel, which would start and end in Manhattan. But first, I had to peel myself away from the opulence of the Plaza, and my Gatsby Suite: a $2,500 (£1,911)-a-night Art Deco dream created to honour Australian film director Baz Luhrmann’s 2013 movie, The Great Gatsby, starring Leonardo Di Caprio.

In 1922, a year after giving birth to their daughter, Scottie, the Fitzgeralds swapped the hedonism of Manhattan’s Jazz Age nightlife for Long Island’s North Shore, a waterside enclave of wealth a one-hour train ride from Manhattan. It was known as the Gold Coast in its heyday, flecked with glittering Gilded Age mansions, a few of which you can still visit today. For a short while, this was where the Fitzgeralds raised their daughter while mingling and partying with their new elite neighbours. And it was this lifestyle that influenced Fitzgerald to write The Great Gatsby.

At Penn Station in Midtown Manhattan, I hop on the Long Island Railroad. It’s not long before I pass through the…

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