THE BLOG
12/11/2012 07:35 am ET Updated Feb 10, 2013

A Weekend Passport To Old-School New York

New York is the kind of city where nostalgia lies around every bustling corner. Even as the modern-day Big Apple excels in the ultra avant-garde everywhere from the fashion runway to molecular gastronomy to street art, the slightest provocation (the tinkle of a jazz piano, the glint off an Art Deco skyscraper) can send you hurtling back in time to a more classic epoch when Gotham was just coming into its own as a world city. From revisiting the cocktailing culture of the Roaring 20s to the skyscraper-building frenzy of the 1930s, here are our favorite ways to spend a weekend tipping our hats (and our glasses!) to Old World New York.

Friday Night:
5:30 p.m. - For a totally immersive Old World experience, check in at The Carlyle in the opulent Upper East Side. This timeless Art Deco property is known for playing host to presidents, royalty and movie stars. While the amenities (ranging from a shopping arcade to a spa) are up-to-date, the discreet, friendly service is quintessentially traditional (think white-gloved elevator operators).

7:00 p.m. - You won't have to leave the comfort of The Carlyle to kick off your weekend. To toast your trip with a celebratory drink, slip into Bemelmans Bar, a swank 1930s piano bar with deep leather banquettes and perfectly mixed classic cocktails.

8:30 p.m. - The time warp continues in the onsite supper club Café Carlyle, where things really swing. You can indulge in caviar and coq au vin while tapping your toes to classic cabaret performances that recall a jazzier age.

Saturday:
9:00 a.m. - Jumpstart your day with coffee and breakfast treats at nearby EAT. The Upper East Side bakery/cafe updates classic New York deli fare with a gourmet twist. Don't miss the to-die-for basket of bread with jam!

10:30 a.m. - Spend the morning gazing skyward and then reaching new heights as you tour New York's most iconic skyscrapers. First, swing by the Chrysler Building, which, when it was completed in 1930, held the title of the tallest in the world. Its unique form highlights the glamour of the futuristic 1920s Machine Age aesthetic by incorporating elements from Chrysler's luxe automobiles into the architecture.

The Chrysler Building only held on to its "World's Tallest" title for a mere 11 months, trumped by the Empire State Building in 1931. At 103 stories, the striking Art Deco structure managed to hold onto its crown for close to four decades. You can take one of the building's 73 high-speed elevators to the 86th floor observation deck, or, for a premium fee, you can go all the way up to the 102nd story, where you'll unquestionably be at the top of the town.

1:00 p.m. - Pop down to Union Square for a seafood lunch at Blue Water Grill. The restaurant has a whiff of Old World with lofty marble ceilings of the former Metropolitan Bank building. You can get your jazz fix in the lower-level lounge, while the outdoor terrace boasts views of Union Square Park (perfect for people-watching).

2:30 p.m. - Spoiler alert! You'll be catching a show tonight, so spend the afternoon choosing a new get-up for the evening at one of our classic department store picks (all favorites in the 1920s). Housed in a Madison Avenue high rise, Barneys New York offers a mix of newly discovered hot designers and classic standbys (plus eye-catching window displays). The decadent Art Moderne interiors at Saks Fifth Avenue are filled with mini-boutiques for top designers (à la Chanel and Prada) and one of the most fabulous collections of shoes in the world (the footwear department is so big it even has its own zip code at 10022-SHOE!). From classic designers to the latest and greatest in contemporary couture, the nine levels of Bergdorf Goodman are packed with fabulous threads.

6:00 p.m. - Slip into your new chic ensemble before sliding down a few fresh oysters at The Grand Central Oyster Bar & Restaurant in Grand Central Terminal. The landmark interior, dating back to 1913, is crowned by vaulted, Guastavino-tiled ceilings, making it an elegant setting for enjoying the catch of the day.

8:00 p.m. - It's show time! You have a couple of stellar options for experiencing one of Manhattan's Old World theaters. You could hop over to the Upper West Side for a live music show at the Beacon Theatre (make sure to secure your tickets well in advance). The Art Deco auditorium, originally opened in 1929 as a vaudeville hall, was recently restored to its Roaring Twenties glory.

Or, you could go for an all-out gilded extravaganza at Radio City Music Hall, the world's largest indoor theater in the Rockefeller Center complex. Its glittering marquee is a full city block long, its shimmering gold curtain is the largest in the world, and its grand interiors are the stuff of legends. Since 1933, the biggest names in entertainment, from Sinatra to Ray Charles to Bette Midler, have graced the stage (the Christmas Spectacular featuring the Rockettes remains an annual sellout).

11:00 p.m. - End the evening with a refined drink at King Cole Bar in the lobby of the The St. Regis New York hotel. From the towering ceilings to the tuxedoed waiters, the low-lit space evokes the romantic age when cocktailing was the height of fashion. Don't miss the Red Snapper cocktail (a version of the Bloody Mary which debuted here in 1934).

Sunday:
9:30 a.m. - You can't get more classic than a New York bagel for breakfast. For your fix, head over to Daniel's Bagels, a quintessential NY bagel joint with mouthwateringly good smoked fish and spreads (we especially love the calorific fried egg and cheese on an everything bagel).

11:00 a.m. - There's no grander way to make an exit from New York than at Grand Central Terminal. The enormous Beaux-Arts treasure underwent a thorough restoration in the 1990s. Rediscovered treasures include a dazzling gold-leaf-encrusted celestial mural on the ceiling of the main concourse; the Whispering Gallery (where you can throw secrets around a curved wall to your waiting friends); and imposing statues of Minerva, Hercules and Mercury on the exterior. Grab an audio guide from the kiosk in the terminal's main hall.

1:00 p.m. - If the rumbling of your tummy is getting louder than the rumbling of the trains coming in to Grand Central, make your way to the surprisingly well-stocked food court in the basement, where you can nab everything from Ciao Bella gelato to Two Boots pizza to famous New York cheesecake from Junior's.

2:30 p.m. - If you want just one last parting cocktail before your train whisks you off to your destination, cap off the weekend with a "Flapper's Delight" or a classic Manhattan (one of the best we've tasted) at The Campbell Apartment, an opulent, Old World cocktail cathedral hidden in Grand Central Terminal. Formerly the private office of a 1920s banker and tycoon, the bar evokes the splendor of Old New York with its beautifully hand-painted ceiling, stained glass faux-windows, mahogany woodwork and antique rugs. It's such a completely immersive experience that when you exit the station, your eyes won't just have to adjust to the sunlight -- they'll have to adjust to the century!

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-- Emily C. Brands and Rachel B. Levin, www.thepurplepassport.com