Check into a slick stay. Gatsby liked New York grand dame The Plaza and the hotel has returned the favor, creating an F. Scott Fitzgerald suite. But she’s not the only swell dame in town. A few blocks south is the New York Palace hotel, memorialized by Gossip Girl, the aughts answer to Gatsby society. Or head further downtown to the Gramercy Park Hotel, the nexus of New York party and privilege, where Bogart got hitched, Babe Ruth got drunk and the Kennedys once lived.
For dinner, book the secret wine room of the 21 Club, once New York’s most famous speakeasy. A waiter inserts a skewer into a crack in a cement wall to open a secret door into the wine room, which holds 2,000 cases of wine, including the private collections of Elizabeth Taylor, Eva Gabor and Sammy Davis Jr. Afterwards, head downtown to the McKittrick Hotel, site of the immersive theater experience Sleep No More (book in advance). Akin to finding yourself in the middle of a movie, you’ll wander masked through floors of rooms, stumbling upon lover’s quarrels in hotel lobbies, murders in banquet halls, a hospital ward, a mist-shrouded forest. After the choose-your-own-adventure journey, you emerge in a Weimar-style cabaret to sip absinthe while a siren croons hot jazz.
Even if you’re not staying at The Plaza, you should make a special trip for tea in the Palm Court where characters Nick Carraway and flapper Jordan Baker rendezvoused. Sip champagne cocktails while dining on curried lobster salad and smoked salmon with wild sturgeon caviar. While you’re there, check out the hotel’s exhibit of props and costumes from the movie as well as the 20s barware and Deco décor on sale in the boutique. Continue the retail binge with a visit to The Family Jewels, a 2,000 square foot vintage emporium in Chelsea, and NY Vintage, where costumers for Boardwalk Empire, Grey Gardens and Mad Men source their historic duds. See dresses from the movie designed by Miuccia Prada and Catherine Martin at Soho’s Prada flagship (on view until May 12th), and score some dapper duds at Brooks Brothers, which helped create Leonardo DiCaprio’s Gatsby getups. Take your glad rags out on the town with a little juice joint bar crawl. Head past the faux toy store façade and over to a large bookcase, which opens to reveal The Back Room, a copper-ceiling’d Art Nouveau den, where beers come in paper bags and drinks in vintage tea cups. Then, pull up a café chair at The Slipper Room, a neo-burlesque den of sin five blocks away. The shy should retreat to the balcony as tassled and teasing acts often tickle, lick and shimmy their way through the floor crowd.
If you’re headed to the city June 15-16th or August 17-18th, take the short ferry over to leafy Governor’s Island for the Jazz Age Lawn Party. Costumed New Yorkers dip into picnic baskets amid 20s motorcars and antique gramophones while cool cats dance the Charleston to jazz band Michael Arenella and His Dreamland Orchestra. Not your bag? Then kick back on a 20s wooden yacht, the de rigeur toy of Jazz Age oil barons and Wall Street tycoons. They offer leisurely Sunday brunch cruises, circumnavigating Manhattan, as well as evening jazz sails.