It’s no coincidence that the Vanderbilts, the Roosevelts, the Kennedys, and Gossip Girl all call the Upper East Side home. Manhattan’s toniest neighborhood will empty your wallet faster than you can spot a toddler in Tory Burch flats (which, at last count, was approximately 10.8 seconds). But as long as you’re feeling flush, there’s plenty of entertainment to be found among the city’s upper crust.

When to go: Any time of year is fine, but if you keep a close eye on the tabloids, you can probably catch a famous couple leaving Lenox Hill Hospital (77th Street between Park and Lexington Avenues) with proof of their “Baby Joy!”… Blue Ivy Carter made her debut here in January.

Approximate travel time: If you take the preferred mode of UES transport–taxi–you should be there whenever midtown traffic allows. Luckily, the TV in the backseat of the cab should keep offspring preoccupied.

What to do: The southernmost gateposts of the Upper East Side, the Plaza Hotel and FAO Schwarz (59th Street and 5th Avenue), are a great place to start–take the kids for tea at the Palm Court in Eloise’s old stomping ground and the browse the racks in the country’s oldest toy store, which still manages to seem opulent even in today’s consumer culture.

Speaking of shopping, why not indulge in the UES’ favorite pastime? Posh kids’ boutiques line Madison Avenue; get them decked out at Bonpoint (91st Street), Bambini (82nd Street) or Petit Bateau (82nd Street) to blend in with the blue bloods. They can also play dress-up for less at Let’s Dress Up (345 E. 85th Street between 1st and 2nd Avenues), which offers drop-in playtime hours–check their website for details. And less prim and proper fun can be had at Art Farm in the City (91st Street between 1st and York Avenues), which offers craft projects and even an urban petting zoo, with animals that–befitting their zip code–fit nicely inside a standard purse.

If your children are either very cultured or very patient, take them to one of the Upper East Side’s many museums. The Metropolitan Museum of Art is vast and noisy (perfect for littler kids), but art lovers of all ages will appreciate the twisted shape of The Guggenheim (89th Street and 5th Avenue–just don’t let them bring a skateboard!)

Where to eat: Have breakfast in style, if not exactly in Wonderland, at Alice’s Teacup Chapter III (81st Street between 2nd and 3rd Avenues), where you can order savory omelets, fluffy pancakes, or “Alice’s Mad Morning Tea,” a three-tiered tray of scones, eggs, and granola. Grab a midday bite at E.J.’s Luncheonette (73rd Street and 3rd Avenue), a classic diner with plenty of kid-friendly options. And save room for dinner at Serendipity 3 (60th Street at 3rd Avenue), which serves up hearty, non-threatening American cuisine plus a dessert menu that’ll have their eyes rolling back in their heads.

How to dress: Bring your A-game. While the UES is a tourist destination, if you want to look like a native you’ll need to wear your Sunday best: crisp pastels in spring and summer, tweed and furs in fall and winter–with designer labels if you can swing ‘em.

Bonus: Tour Gracie Mansion (88th Street and York Avenue), the “official residence” of Mayor Michael Bloomberg–even though he’s never actually lived there.

Cost of trip: Just put it on your credit card and try not to think about it.

Got any other must-see Upper East Side hotspots? Tell us in a comment below.

— Una LaMarche

Photo credit: FAO Schwartz Piano via FacebookEJ’s Luncheonette via EJ’s website, Dress Up via Facebook, Brooke and Kids via Facebook.