24 Hours in The Hamptons

Whether you’ve been or not, there’s a clear mental picture that practically paints itself when you hear “The Hamptons.” For some, it’s The Great Gatsby—million dollar mansions, fast cars, and swanky dinner parties. For others, it’s The Real Housewives of New York—polo matches, pinot grigio, and clearly staged catfights. Then there’s the Goop version—Gwyneth sipping a turmeric tonic in her perfect home, surrounded by girl bosses and jade rollers. Well, you’re all right. Located anywhere from 90-90,000 minutes from New York City (depending on traffic), The Hamptons is a uniquely diverse and compelling stretch of beach towns. Each “Hamlet” or “village” has its own vibe. Sag Harbor feels like a tiny sailing town, adorably stuck in the 1950s. Montauk is the Venice Beach of Long Island’s South Fork. Easthampton is clad with upscale boutiques and, “Stars, they’re just like us!” coffee shop sightings. The best part about the Hamptons is that you don’t have to choose one version. Route 27 (Sunrise Highway) passes through each town, so you can say you saw it all.

We’ve rounded up a mix of tips that run the gamut from chill to chic, hitting just about every hood in the Hamptons. You should stay for a weekend, but if you only have 24 hours, here’s the deal…

12PM: On Deck

Start your Hamptons trip off with some fresh seafood on the deck at Duryea’s. Treat yourself to one of their delicious towers and sample all of the local catches.

1PM: See The Light

Brought to you by the celebrated Dia Art Foundation, The Dan Flavin Art Institute permanently exhibits nine of Flavin’s prolific fluorescent light pieces, created between 1963 and 1981 during his summers in the Hamptons. Bonus: the stage is set in a revamped Bridgehampton fire station with a rotating exhibition on the main floor and Flavin’s gallery upstairs.

The Dan Flavin Institute photo via @comwu

2PM: Summer In A Bottle

You know that gorgeous floral-covered bottle of rose that floods your IG feed every summer? That’s Wölffer Estate’s infamous “Summer In A Bottle” rosé. Visit the vineyard for a cellar tour and/or tasting and make your followers jealous they got their Wölffer from a liquor store.

3PM: Say Cheese!

If you’re anything like us, wine drinking leads to cheese cravings. Cavaniola’s Gourmet is your dairy dream come true (unless you’re lactose intolerant, then it’s your worst nightmare and you should skip this tip). The Sag Harbor shop has an incredible assortment of cheese and other delectable accouterments that are bound to make your charcuterie envious.

4PM: Guest Of The Year

Didn’t have time to grab a gift for your generous Hamptons’ host? Look no further than Loaves & Fishes Cookshop for the most carefully curated collection of kitchenware and home goods. Take our advice and you’ll definitely be invited back next summer.

5PM: Brewmasters

In a world oversaturated with Starbucks and coffee shops in general, Left Hand Coffee stands out from the pack. Their slogan “In Coffee Veritas” (In Coffee We Trust), reflects a palpable commitment to serving the best brews in their insanely chic Montauk locale. Sip it at the shop, take it on the road, or grab some beans for the crib.

6PM: Pull Over

Clam Bar has been satiating the seafood cravings of drivers-by for over thirty years and is a non-negotiable stop during your Hamptons trip. Pull over on The Sunrise Highway and basque in the no-frills ambiance. Plus, have a beer from Montauk Brewing Company while your oysters are being shucked.

Clam Bar photo via @jane_lilly

7PM: You Need Therapy

We all do. Montauk Salt Cave invites you to relax and breathe in Halotherapy. Huh? “Halotherapy, aka salt therapy, is an alternative treatment for a wide variety of ailments and conditions, such as asthma, allergies, inflammation, and even the common cold.” Regardless, it’s pink and immersive, and the lighting will make your selfie go viral.

8PM: Boat Life

Don’t forget your on an island. (Technically it’s a peninsula, but water on three out of four sides counts.) Take a Dramamine and book an experience at Mon Tiki. You can charter a private vessel or hop on one of the daily sunset cruises, either way, you’re doing it right.

9PM: Vine Street Cafe

If you went with a private charter, take a trip to Shelter Island. Or you can “rough it” and load your car on the public ferry. Make sure you look at the schedule, though, or you’ll be stranded on the island with nothing to do but eat and drink at Vine Street Cafe, which is actually not a bad situation. 

10PM: Plan B

Hate boats? All good. World Pie is open until midnight 365 days of the year, serving delicious wood-fired thin crust pizza in Bridgehampton. Hate pizza? They have pasta and salad. Hate pasta and salad? Go home.

11PM: Cup Or Cone?

Scoop Du Jour is the epitome of dessert heaven. Candy, donuts, ice cream, and all your favorite sweet treats. It’s summer and you’re on vacation, but hit the ATM before you binge because it’s cash only.

12AM: Up To You

If you’re even slightly into the sushi scene, you probably haven’t stopped hearing about Sushi By Bou. Rapidly expanding across the country, Sushi By Bou offers modernized 30 or 60-minute Omakase options in their new Southampton locale. “Omakase” translates to “I’ll leave it up to you,” so let Bou do his thing behind the bar.

1AM: Turn Down For What

Next door to Bou is one of the hottest spots in the Hamptons for dinner, drinks, and people watching. Southampton Social Club has incredible American fare and an even better outdoor dance floor. Get involved in the party or watch the crowd turn up from the comfort of a backyard cabana.

South Hampton Social Club Facebook

2AM: Don’t Be Silly

The Hamptons Police Department does not play around when it comes to drunk driving. And neither should you. Make your mama proud and opt for a ride on The Hampton Hopper. It’s only $5 and stops basically everywhere you want to be.

3AM: The Stephen Talkhouse

If you Google “best bar in the Hamptons,” you’ll no doubt find your way to The Stephen Talkhouse. Since opening in 1970, the down-to-earth live music venue has been a favorite among locals and visitors alike. HINT: Just call it “Talkhouse,” or everyone will know it’s your first time.

4AM: Take A Dip

There’s a 99.9% chance that wherever you’re staying has a hot tub/pool situation. There are no “after hours” clubs in the Hamptons, so take the party back to the house and go for a (skinny) dip.

5AM: Look Up!

The Hamptons’ night skies boast a breathtaking view of all those constellations whose names you once knew, but can’t recall. The further out East you are, the less light pollution from NYC, so Montauk would be an ideal situation.

6AM: Hangover Helper

There’s nothing like a bagel to bring you back to life. Be the first in line at Goldberg’s to get back on your feet. There’s a location in practically every village, so you can army crawl your way to salvation wherever you’re staying. You can’t go wrong with their menu, but we usually opt for “The Hungry Man” breakfast sandwich when the hangover is serious.

7AM: Ctrl+Alt+Z

Feeling guilty about all those tequila shots and that delicious breakfast bagel? Undo the damage at SLT. Their dynamic, hands-on sessions will snap you out self-loathing mode and back into bikini mode.

8AM: Eat Local

Ignore the urge to stock up at Whole Foods on your way to The Hamptons and get your fresh food fix at Round Swamp Farm. They have locally farmed produce, freshly baked goods, and catches of the day that will boost your trip’s sustainability score.

9AM: Sun Daze

You’re by the beach, so you should go to the beach. Our top pick is Cooper Beach in Southampton. Get there early to avoid parking problems and territorial tourists, then sink your feet in the fine white sand and shhhh.

Cooper Beach photo via @fitzpix23

10AM: Dollar Drafts

The Hamptons is not cheap, but we’ve got a beer hack for you. Liar’s Saloon has dollar drafts twenty-four hours a day. It’s not very “Hamptons,” but it gets the job done so can spend all your leftover beer money on seafood towers.

11AM: H.A.G.S.

Unless you have a ride or have chartered a helicopter (in which case you should be the one giving us tips on how to be you when we grow up), you’ll have to find your way back to the city on the train or The Hampton Jitney. Opt for an upgrade and book an Ambassador Jitney for twice the leg room, free snacks, and an outlet at every seat. Go on, you deserve it.

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