Avoid the Brooklyn hipsters here.

It’s the New York of Edith Wharton and Woody Allen, of Holden Caulfield and Tom Wolfe. Long dismissed as the dull playground of the ultra-rich, the area’s very uncoolness is making it a welcome hipster-free alternative to Brooklyn et al. Architecturally, this is where you’ll find the brownstones of New York’s Gilded Age along with the high-rises of the very rich and very famous that line Park Avenue. (740 Park is so famous, it has its own book.)

Getting There

A plane is like Manhattan—helpfully divided into different segments offering different things. If you fly the Cathay Pacific Vancouver-NYC red-eye, the flight is actually a continuation from Hong Kong, meaning you get all the classes: you can do Upper East Side-style (First Class), Midtown efficiency (that’d be Business) or the great surprise that is Downtown (the steal that is Premium Economy—pocket some extra $$$ for more skinny jeans). And there’s good old Economy too, for when you’re bringing the kids.

Henry Clay Frick's modest home.


No structure captures the manners and flow of the neighbourhood better than the Frick Collection. Across Fifth Avenue sits the everything-to-everyone behemoth that is the Metropolitan Museum of Art, but here, in industrialist Henry Clay Frick’s former private mansion, you’ll get a daguerreotype of the collecting life of one of America’s wealthiest citizens at the turn of the last century. If you’re looking for Rothko, head downtown, but if your tastes run to masterpieces by Fragonard, Turner, Constable and Titian displayed in muted opulence, then there may be no finer museum in the world.


The Upper East Side is a place where you inherit furniture, not buy it. For a fascinating shortcut, head to Sotheby’s and see what’s being hawked this week. In between the big November and May auctions there are dozens of weekly auctions dealing with slightly less rarefied goods (from lithographs to mid-century furniture to watches) for the non-oligarchs among us.

The bastion of all things WASP-y, Ralph Lauren's the Polo Bar.


Daniel Boulud’s combination of sedate decor, impeccable service and consistently amazing food is tailor-made for this neighbourhood. His jaw-droppingly expensive restaurant Daniel is always flawless, but if you head 11 blocks north, his Café Boulud has the same insane standards, a slightly more lively interior and a weekend dinner prix fixe at $68. If you want a little more buzz but the same ultra-WASP-y vibe, head 10 blocks south to the new and impossible-to-get-into the Polo Bar on 55th, where Ralph Lauren (the brand, not the man) curates classic dishes (shrimp cocktail, roast chicken) in a room so loaded with studded furniture and horse paintings that it resembles Aunt Muffie’s place in Sagaponack.



From the Pierre hotel you may just be able to see the tour buses and gaggles of crowds gumming up every square inch of space at the Plaza, the other Jazz Age lodging that has aged less well. Unlike its neighbour, the Pierre has maintained its position as the guardian of dignity and manners (right down to the human operators in their leather- and wood-clad elevators) while still offering rooms the way they used to be—huge and often with kitchens. And a bonus? Actual New Yorkers live here. (In fact, one of the penthouses was listed for sale in 2013 . . .for $125 million.)