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鈥檚 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鈥檙e interested in sunbathing, cycling, hiking or surfing. 

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鈥檛 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鈥檛 one for celebrity sightings, consider the shoulder season. Fall is a wonderful 鈥� and colorful 鈥� 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鈥檛 have to agonize over getting a table at the most coveted restaurants like . Spring is similar in that the tourists won鈥檛 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鈥檙e 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鈥檙e 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鈥檒l barely make it in time for dinner before you feel like you鈥檙e turning around to beat the traffic back to the city on a Sunday. 

If you can swing three nights, that鈥檒l 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. 

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鈥檛 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鈥檙e interested in seeing more than just what鈥檚 walkable from where you're based, be that Sag Harbor (there鈥檚 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鈥檚 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鈥檛 easily be able to access all of the shops and restaurants if you take the train. provides very good access to towns and villages, and there鈥檚 a high-end bus service called The Hamptons Streamliner by  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鈥檛 really go wrong, especially if you鈥檝e packed a picnic. While the town鈥檚 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

in Sagaponack is a popular stop on the winery tour. The sparkling ros茅 cider helps explain the winery鈥檚 appeal, but throughout the year, it hosts various events and dinners that showcase its wines. In nearby Bridgehampton, is another great option for wine tasting, or even if you鈥檙e just planning on eating some delicious cheese and charcuterie against a gorgeous backdrop.

Load up on provisions and plan a picnic

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鈥檚 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, 鈥檚 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 , which is rarely the case), and now that I have a new puppy who is just learning to play Frisbee, I can鈥檛 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鈥檛 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鈥檚 a good idea to pack your own provisions if you鈥檙e on a budget. Shopping varies, of course, and if you鈥檙e looking for a statement piece of furniture from  or a giant piece of art to hang in your bedroom, you can find it here, but you鈥檒l 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. 

• Night at the : US$1595 in high season; US$695 in low season

• Night at a 4-bedroom Airbnb: US$1100 in high season; US$150 in low season

• Dinner at in Sag Harbor: US$100+

• Breakfast at John鈥檚 Pancake House in Montauk: US$15 

• Wine tasting at Channing Daughters: US$28 for a starting flight 

• Jam and bread from Loaves & Fishes: US$25

What to pack

Your Hamptons鈥� 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 鈥� it鈥檚 cold out here on the water!

Reserve in advance

Again, this is seasonally dependent, but if you visit the Hamptons in high season, you鈥檒l 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鈥檙e heading east on a Friday, and it鈥檚 even more true if you鈥檙e 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.