What was Manhattan like in the Roaring Twenties? See for yourself

It’s been a century since The Great Gatsby was first published, shining a light on extravagant New York lifestyles in an era that went down in history as the ‘Roaring Twenties’. It was the decade that paved the way for Manhattan’s Chrysler Building and other progressive style icons, creating an anything-goes atmosphere for jazz-fuelled parties, Champagne afternoons and secret affairs in Prohibition speakeasies. And, 100 years later, it’s still possible to experience this defining spirit in one ultimate day out in New York City.

(It’s the 100th anniversary of The Great Gatsby and New York is ready to party, old sport.)

8am: Breakfast at the Square Diner

Time travel back to 1922 with a hearty breakfast at the Square Diner, an original train-car-style cafe that’s been serving the Tribeca community for over a century. Inside you’ll find antique black-and-white photos decorating the wood-panelled walls, weathered chrome fittings and snug leather booths. The breakfast menu is extensive; try the fluffy buttermilk pancakes, flipped fresh from the hot griddle.

10am: Explore the Rockefeller Center

Ride the subway north to the Rockefeller Center, an art deco complex in Midtown that’s considered one of the most ambitious building projects of the Great Depression era. It’s made up of 19 different sections, spanning an area between Fifth and Sixth Avenues, and split by a sunken garden square. You’ll need a paid ticket to view the spectacular skyline at the Top of the Rock Observation Deck, but visitors can also just wander into the lobby of 30 Rock to admire the razzmatazz of gold detailing splashed throughout the interiors.

12pm: Glad rags at Desert Vintage

Specialising in clothing from the 1900s to the 1970s, this carefully curated boutique on the Lower East Side is the place to go for glamorous one-of-a-kind gems. Catering to both men and women, its wares include everything from cases of twinkling jewellery to rails filled with sharp suits and flapper dresses — perfect for foxtrotting into a lavish Gatsby-style party, which brims with Champagne and gossip.

2pm: Afternoon tea at the Palm Court

For over 115 years, The Palm Court restaurant has been serving New York’s movers and shakers, including The Great Gatsby author F Scott Fitzgerald and 1930s movie goddess Marlene Dietrich. Cocooned inside the marble grandeur of The Plaza hotel, the interiors remain a masterclass in restrained elegance, taking inspiration from the lush greenery of nearby Central Park. Book ahead for the afternoon tea service, where dinky roast beef sandwiches and freshly baked scones are served under a glass-dome ceiling.

4pm: Visit the Chrysler Building

Swing by the soaring Chrysler Building, one of New York’s most beloved art deco skyscrapers, in midtown Manhattan. This masterpiece remains the tallest brick building in the world with a steel framework. These days it’s a private office building, but fans are allowed to take a peek inside the lobby to view the original interiors, including geometric patterned elevators and a vast ceiling mural by the artist Edward Turnbull, depicting the flat-capped workers who constructed the skyscraper.

6pm: Sunset supper at the Empire State Building

Less than a mile south of the Chrysler, the iconic Empire State Building is another art deco beauty. Completed in 1931, it’s since been immortalised in pop culture, with a starring role in movies such as King Kong and Sleepless in Seattle. Today, at the base of the building you’ll find the swanky State Grill and Bar bistro, known for its burgers and steaks. Buy a dine-and-observatory package, to eat at the restaurant before being whizzed up to the observatory deck on the 86th floor to catch the glowing sunset.

9pm: Catch live Jazz at the Campbell Bar

Hidden in plain sight, The Campbell Bar is situated inside Grand Central Terminal. In the 1920s it served as the glittering offices of the Jazz Age financier John W Campbell. Later, it fell from grace and became a railroad jail, of sorts, before being restored to its former Beaux Arts architectural glory. Take a seat in the cocktail lounge to gaze up at the hand-painted Florentine–inspired ceiling. Toe-tapping live jazz sets are hosted from Friday to Sunday.

10pm: Drink cocktails in teacups at the Back Room speakeasy

It’s certainly not easy to find the entrance to this clandestine hideaway. You’ll first need to follow the signs for ‘Lower East Side Toy Company’, then continue along an alleyway and down a hush-hush flight of stairs. But that’s the charm of the Back Room, one of only two speakeasies that operated during Prohibition, which are still in existence today. In the 1920s the underbelly of New York mingled here, including notorious gangsters of the era, but today it’s a hip hangout with gin and elderflower cocktails served in dainty teacups. Pull up a chair and let the Jazz Age party begin.