Ah, the Hamptons! These picturesque Long Island towns are littered with cute shops and upscale seafood restaurants, pristine beaches, lush wineries and a super-chic crowd. There’s art, hiking and antiquing, museums, boat rides, and knock-out road stands and farmers’ markets full of incredibly fresh produce.
The collection of towns on the island’s eastern end where numerous celebrities own multi-million dollar homes and in-the-know New Yorkers summer, is also totally approachable to any traveler interested in an escape from the city to a less hurried, well-rounded way of life. In the Hamptons, nature awaits, whether you’re interested in sunbathing, cycling, hiking or surfing.
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When should I go to the Hamptons?
This region is undoubtedly most popular in the summer when friend groups flock to house shares for the weekend and wealthy New York City residents decamp for a more relaxed way of living, at least temporarily. If you don’t mind a scene (and especially if you enjoy one) peak summer is an excellent time to check out the Hamptons.
If you prefer a more mellow crowd and aren’t one for celebrity sightings, consider the shoulder season. Fall is a wonderful – and colorful – time of year to hang out in the Hamptons, and if you go early enough in the season, you might just get a couple of beach days yet.
Besides that, the foliage is fantastically bold, the apples are ripe, and you won’t have to agonize over getting a table at the most coveted restaurants like LDV at the Maidstone. Spring is similar in that the tourists won’t have landed en masse, which results in a slower pace and plenty of flowers to stop and smell. While some places remain open year-round, some establishments close in the dead of winter, so if an off-season visit is what you had in mind, check to make sure the things on your list are operating.
How much time should I spend in The Hamptons?
The Hamptons make for a great weekend trip if you’re living or staying in the New York Metropolitan area, but even that may not be enough time to explore, depending on the time of year you’re visiting. That is, if you plan a July or August weekend and take the Jitney (more on this mode of transportation later) or drive out on a Friday, you’ll barely make it in time for dinner before you feel like you’re turning around to beat the traffic back to the city on a Sunday.
If you can swing three nights, that’ll allow for a more relaxed vacation, but four nights helps you justify a loosey goosey itinerary; after all, part of the joy of a Hamptons visit is meandering here and there.
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The amount of time you need in the Hamptons also depends on your game plan: Are you trying to visit multiple towns and get a full feel for each? Or are you staying at an inn in Sag Harbor with an agenda that involves eating and drinking well, maybe some boutique shopping with an afternoon stroll on the beach?
You don’t need a ton of time, but the more time you have, the more you can explore.
Is it easy to get in and around the Hamptons?
Having your own vehicle is best if you’re interested in seeing more than just what’s walkable from where you’re based, be that Sag Harbor (there’s a Whaling and Historical Museum here), East Hampton (the Marine Museum is worth a visit), Amagansett, Montauk (the Lighthouse is a must-see attraction) or one of the other towns or villages in The Hamptons. If you’ve got access to a car, you’ll have more freedom to hop around.
While you may be able to get an Uber or Lyft, on peak weekend nights, it may not be easy, and it’s bound to be pricey. The Long Island Railroad goes all the way to Montauk, one of the most idyllic towns in the Hamptons, but you won’t easily be able to access all of the shops and restaurants if you take the train. The Hampton Jitney provides very good access to towns and villages, and there’s a high-end bus service called The Hamptons Streamliner by Blade that some may prefer over driving. It depends on your plans, and a car is certainly not essential.
Top things to do in the Hamptons
Hang out at the beach in Montauk
Ditch Plains; Gin Beach; Sunset Beach: You can’t really go wrong, especially if you’ve packed a picnic. While the town’s beaches get plenty crowded in the summer months, the lack of boardwalks or major developments means a more relaxed vibe. Brush up on surfing skills, go kayaking, or listen to the breaking waves as you lay back with a book.
Visit the wineries
Wölffer Estate Vineyard in Sagaponack is a popular stop on the winery tour. The sparkling rosé cider helps explain the winery’s appeal, but throughout the year, it hosts various events and dinners that showcase its wines. In nearby Bridgehampton, Channing Daughters Winery is another great option for wine tasting, or even if you’re just planning on eating some delicious cheese and charcuterie against a gorgeous backdrop.
Load up on provisions and plan a picnic
Loaves & Fishes Foodstore has been open for more than 40 years; and even before you step inside, the sweet, yeasty aroma of freshly baked bread and other pastries and sweet treats tells the story. You’ll also find an enticing array of prepared foods here, from grilled citrus salmon to curried egg salad, and rotisserie ducks and chickens. Jams and honey and other too-cute-to-resist items line the shelves.
Get your hike on in a nature preserve
They say as you get older you develop an appreciation for birds, and if that’s not yet true for you, trail walking in the Hampton Bays Nature Preserve, with its easy-to-navigate paths and gentle aura, may just be powerful enough to convert you. In Sag Harbor, Long Pond Greenbelt’s Nature Center is open from April through October. This is also the time to check out Sagg Swamp, an area made up of swamp, pond, bog, stream and upland forest ripe for wildlife sightings.
My favorite thing to do in The Hamptons
Every since I watched Eternal Sunshine of the Spotless Mind, I longed to visit Montauk (IYKYK), and when I finally made it there after I first moved to New York City almost 20 years ago, it did not disappoint. Before my senior dog passed away last year, I loved nothing more than to pack up the car and take Odie to a Montauk beach (the beaches are all dog-friendly, which is rarely the case), and now that I have a new puppy who is just learning to play Frisbee, I can’t wait to introduce him to one of my all-time favorite New York City escapes.
How much money do I need for the Hamptons?
The Hamptons definitely don’t come cheap. While there are some campgrounds, most people opt for an Airbnb or VRBO or stay at a charming inn. In high season over a weekend, accommodation costs rise exponentially. Food also tends to be on the pricier side, even at snack shops selling bagels and prepared sandwiches and coffee. It’s a good idea to pack your own provisions if you’re on a budget. Shopping varies, of course, and if you’re looking for a statement piece of furniture from Monc XIII or a giant piece of art to hang in your bedroom, you can find it here, but you’ll likely pay a premium. Seek out consignment clothing stores and shops selling local artisan goods like a cute wine corkscrew or a set of artsy coasters.
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Night at the Roundtree Amagansett: US$1595 in high season; US$695 in low season
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Night at a 4-bedroom Airbnb: US$1100 in high season; US$150 in low season
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Dinner at Lulu Kitchen and Bar in Sag Harbor: US$100+
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Breakfast at John’s Pancake House in Montauk: US$15
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Wine tasting at Channing Daughters: US$28 for a starting flight
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Jam and bread from Loaves & Fishes: US$25
What to pack
Your Hamptons’ wardrobe, of course, depends on the time of year you visit but the vibe here is distinctly preppy-casual. Khakis and white sweaters, clean white sneakers, and flowered sundresses are all common sights. In summer, plan for bathing suits, sun dresses, shorts and nice tennis shoes. Fall is all about layering, pack those cozy sweaters, water-proof outer layers and duck boots and don’t forget a knit hat. In the winter add a down coat or water-resistant parka – it’s cold out here on the water!
Reserve in advance
Again, this is seasonally dependent, but if you visit the Hamptons in high season, you’ll want to make restaurant reservations in advance. The popular ones go fast, so get ready with those Resy notifies!
Plan for traffic, and then add another hour
This advice is especially helpful if you’re heading east on a Friday, and it’s even more true if you’re going all the way to Montauk. That single highway backs up quickly, so plan ahead with playlists and podcast downloads and plenty of water and snacks.