A Guide to Hamptons Debauchery

Where to eat, drink, party, and relax on the hottest stretch of Long Island.

Ah, the Hamptons—that 45 mile stretch of Long Island made famous in Weekend at Bernie’s. (Or was it Gossip Girl? Let’s not admit we watched Gossip Girl…) This place is a rite of passage for sub-30 east coasters, with a winning combination of beaches, nightlife, and (often overpriced) lobster. Think of it as the perfect escape from New York City in the summer.

This string of quaint towns first gained popularity back in the 80s, then a haven for artists and surfers. In the past decade, it’s become a trendy destination for more moneyed visitors. This means an increase in fine dining, celeb sightings, and places that accept AmEx.

“The Hamptons have changed drastically in the past five years,” says Ian Duke, owner of Southampton Social Club. “Our consumers have become more educated…meaning greater expectations for businesses.”

To meet increasing demands, the Hamptons have experienced a major boom in restaurants and nightlife—making it the perfect destination for a summer weekend. Just remember: Your bank account only has to stay in the green until the 10 PM Jitney on Sunday.

Where To Stay:

Most people opt to stay in a share house, where large groups of friends pool their money, divide weekends and strategize on how best to sleep in a bathtub. The lucky few holding golden tickets can skip the share house to crash at the home of a wealthy friend.

But if it’s only one weekend you’re after, try one of the area’s youth-geared hotels. We love Baron’s Cove (Sag Harbor) and Montauk Yacht Club. (The Yacht Club has a killer Saturday brunch party.)

For an active weekend, visit: Montauk, East Hampton, Sag Harbor and Southampton.

To really relax, visit: Amagansett, Bridgehampton, Hampton Bays, and anything west of Riverhead.

Where To Eat:

Food in the Hamptons can be expensive and mediocre, so you need to know where to go. Both Cowfish and Rumba serve great food amongst energetic, beachy atmospheres, but Nick and Toni’s in East Hampton dominates the celeb scene (think Jerry Seinfeld, Alec Baldwin, Martha Stewart).

Those trying to impress a Cooper’s Beach beauty can head to Race Lane for a fancy—albeit expensive—chance to try local delicacies. And for lunch? Head to…well… Lunch. It’s worth the visit just to relive Showtime’s The Affair, but make sure to try the hot lobster roll and seafood nachos while you’re there.

If you’re looking for top-notch grub, head to Sag Harbor. Try Il Cappuccino for Italian, or Beacon for seafood with a great bar scene. If you’re seeking a pretty venue above all else? Tutto Il Giorno takes the cake.

Where To Party:

Those staying west of Bridgehampton must try Southampton Social Club. This club is located in the Hamptons home you’ll never afford, with a combination of outdoor and indoor spaces that are drenched in hydrangeas. Plus, Heidi Klum parties there. Seal of approval? Check.

Photo: Southampton Social Club

The other good watering holes lie further east on the island. You can spend your days in Montauk drinking at either Sloppy Tuna or Cyril’s, then head to Surf Lodge in the evening. Think of Surf Lodge as the beachy sister club of New York’s Jane Hotel, with an accessible beach and live music. (The door, however, is equally difficult.)

Still at a loss? Rachelle Hruska’s Guest of a Guest maintains a comprehensive list of the Hamptons events. One trip to her website can have your weekend scheduled in no time.

Where To Drink:

Wine culture on the North Fork of Long Island is where Napa-Sonoma was fifty years ago — promising, but learning. Go for the atmosphere instead of the tannins, and no one will be disappointed.

The Provence-style Croteaux is a must visit for rosé lovers (a.k.a. everyone), but better wines are found at Martha Clara Vineyards. Their 2010 Riesling is medium dry, and was recently voted the best wine in the state. Channing Daughters is where to go for cool varietals, but the true standout is Sparkling Pointe—they’re even on the list at New York’s famed Eleven Madison Park

Where To Wait Out The Hangover:

Montauk is consistently considered one of the best surfing spots in the world. There are tons of places offering lessons, but I swear by Corey’s Wave. But if you want to get on the water without expelling any calories, Mon Tiki sailing tours are your best bet.

After the beach, head to SagTown Coffee—the only thing better than the iced lattes is listening the next table’s tales from the night before.

And no trip to the Hamptons would be complete without Stephen Talkhouse. The town of Amagansett is somewhat dull, but this 45-year-old music venue has attracted legends like Paul McCartney, Paul Simon and The Velvet Underground. But whatever you do—don’t wear your Hamptons whites. This place gets crowded.


So whether you’re looking for a beachy place to relax or somewhere sunny to party—the Hamptons have got you covered. Start your journey with a trip to the Jitney homepage, where you can buy travel from New York starting at $40.

Photos by Getty Images