Jaunted

Blair Waldorf:
It's hard to stab someone in the back with chopsticks, but the Queen Bee of Constance Billard High School will find a way at Haru. Where price is no object, the upscale sashimi with an amuse-bouche of green-tea tiramisu to follow makes an exquisite meal that won't wreck the fit of your Marni dress.

It may have been the setting to one of her nightmares about Serena replacing her in Mom's affections, but a trip to Henri Bendel to pick up a few things is always a dream--particularly when a private concierge is at your beck and call and a tray of treats from Alison Nelson's Chocolate Bar (on the third floor) awaits your visit. (But she may have to stop shopping there now that "Gossip Girl" has caused a sales spike!)

Blair threw her 17th birthday party at bestie Kati's brother's restaurant with a Guitar Hero competition, but a real Upper East Sider knows how to appreciate the finer things in life--like a night at the New York City Ballet at Lincoln Center. The tragedy of young Blair's life was when she discovered she'd have to cross the park to study the classic Balanchine choreography from the Waldorf box.

Chuck Bass:
The sleazy-but-lovable rake has a soft spot for women and, shall we say, vice, which explains perfectly why he tried to seduce Serena with a truffle grilled cheese at Gilt. The restaurant has since added the notorious sandwich to its menu--for a Bass-worthy $30.

As for whiling away a sunny day in the city, Chuck might enjoy the sensual pleasures of the Shearwater, an 82-foot schooner that cruises the Hudson. (This, of course, is only when the Bass family's boats are in dry docks!) A brunch or sunset sail, though, is a little too pedestrian for an Upper East Side blueblood: We picture our favorite womanizer chartering the whole vessel for late-night romantic rendezvous sometime around midnight.

As for indulging his interest in burlesque, Chuck would do well to swing by The Box on the Lower East Side. Though the buzzing club has lost a bit of its hipster street cred since it opened in 2007, it's still the go-to spot for the young, edgy and lustful--just Chuck's kind of crowd.

Nate Archibald:
Poor Nate: He wants to get out of the Upper East Side grind but just keeps getting sucked back into a world of dirty money and even dirtier secrets. We say he should give up on getting out and embrace that super-rich upbringing while dad is still sheltering assets offshore!

He can start by dropping in at Dorrian's, the WASPiest bar and restaurant in New York. Over an order of wings, he can swap notes with Dartmouth and other Ivy League grads. He might even land a nice new lady--but he'd better plan to hustle her out of the spot before the rowdy crowd shows up later.

Given how much he loves spending time in Central Park, Nate might set up a second date with his sweetie at The Boathouse, overlooking the Lake. A few extra Archibald dollars might shorten the wait at this always-slammed brunch favorite, and might lead to a swanky waterfront table, too.

To really plug into that Old-New-York-Society scene, though, Nate need only hit up Elaine's. The uptown institution is rightly famous for attracting heaps of celebs and dealmakers over the years, but how the mighty have fallen. The food is decent at best, but the prices certainly are keeping up with the times!

Serena Van Der Woodsen:
A Waldorf may find downtown shopping distasteful, but Serena mixes designer dresses with New Cure jeans from APC and clean-lined basics from Uniqlo in SoHo. You don't need to have a trust fund to look this simple and put together--but it helps!

And while she may have put her wild nights behind her, Serena gets legal thrills by dragging her girlfriends to concerts at Terminal 5. Leave the car running outside and get moving to East Village faves Brazilian Girls (Oct. 10) or mash-up master Girl Talk (Nov. 15-16).

Dan Humphrey:
This aspiring writer knows establishing atmopshere is key. Sinking into an overstuffed chair in the Parisian murk of the Bourgeois Pig, he can write in his Moleskine for hours next to a cheese plate or split fondue with his uptown girl.

After a productive morning spent with his college apps, it's time to while away the afternoon at the New Museum on The Bowery. This sparkling, startling monolith holds the edgy exhibits Brooklyn hipsters love and Upper East Side institutions won't touch, like this summer's "After Nature" show, inspired by the work of director Werner Herzog.

And if Herzog has a new movie out, chances are it's at the Landmark Sunshine, where Dan and Vanessa are wont to meet and catch that flick Anthony Lane raved about in last week's New Yorker.

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