This New York Beach Destination Is Also Home to Instagram-worthy Wineries and Cool Boutique Hotels

The weather is getting warmer, and summer is inching closer, which can only mean one thing: Hamptons season is nearly upon us. Read on for the ultimate guide to planning the perfect Hamptons vacation — including when to visit, where to stay, and what to do.

Best Time to Go to the Hamptons

Although the Hamptons is divine in its high season (summer), don't discount Long Island's South Fork during its less popular periods. May and September — two months often referred to as the shoulder season — are great times to visit this New York area. Prices are lower, crowds are thinner, and many restaurants are already open. Plus, because the Hamptons is insulated on all sides, the temperature is a bit warmer than it typically is in New York City, meaning beach weather arrives a few weeks earlier and lingers a few weeks later.

So, don't feel confined to June, July, and August when making your vacation plans. The best time to visit the Hamptons is before the crowds descend and right after they leave.

East Hampton or Southampton?

The two towns that comprise the Hamptons — East Hampton and Southampton — offer vastly different landscapes, and where you end up depends on your vibe. If you're looking for a laid-back, surfer experience, the towns to the east may suit your style: East Hampton, Amagansett, and Montauk have beautiful beaches, excellent restaurants, and a bit more of a relaxed atmosphere. Meanwhile, Springs, which has traditionally been home to locals and artists, remains an under-the-radar destination for those seeking less crowded bay beaches and superlative sunsets.

The town of Southampton, to the west, includes the hamlets of Bridgehampton, part of Sag Harbor, Sagaponack, and Southampton Village. If you're looking for a more formal Hamptons experience, this may be the slice of East End for you. Old estates, galas, and polo matches are de rigueur on this side of the town line. If this sounds like your shade of rosé, raise a glass to all things Southampton.

And what about Westhampton Beach? This village, which lies to the west of the Shinnecock Canal, is not officially considered part of the famed Hamptons, even though it's also home to an impressive array of beachfront mansions along Dune Road. Westhampton's shops, restaurants, and beaches are reason enough for a non-Hamptons visit, if you're looking to get close.

Where to Stay in the Hamptons

Few properties offer a more compelling stay than Montauk's Crow's Nest, where bohemian decor, twinkling Edison bulbs, and a view of Lake Montauk at sunset are just part of hotelier Sean MacPherson's surf-centric vision. The hotel's mix of rooms and cottages runs adjacent to its much-beloved Mediterranean-style restaurant, which is always booming from May through September.

Further west, at the 15-key Roundtree, in Amagansett, guests can explore the boutique property alone or with a furry friend (the hotel is pet-friendly). Beach bonfires, cooking classes, trips to local wineries, and guided walking tours are all signature experiences offered for a bespoke Hamptons getaway.

In Sag Harbor, the 67-room Baron's Cove offers guests a resort experience, with upscale amenities like a pool and on-site restaurant and an incomparable view of the water. Open year-round, there's not a bad time to visit the property, which boasts a cozy dining room and fireplace.

Best Beaches in the Hamptons

Where should you spend your time sunning during your time out east? That's partially a matter of preference. If you're not local to the Hamptons, there are a number of options in terms of paid day parking lots. Cooper's Beach, in Southampton, is a wide, long beach with amenities and a large lot.

In Sag Harbor, Foster Memorial Beach (otherwise known as Long Beach) is ideal for those who prefer to swim in shallow, calm waters or like a little less of a hike from the sand. It's also open to the public.

Amagansett's Atlantic Avenue Beach is open to the public and has lifeguards, concessions, and restrooms, as well as an active surf break. And at the end, in Montauk, Kirk Park Beach's pay lot offers restrooms and a modest hike over spectacular dunes, where, in the heart of summer, lucky visitors may just see whales breaching offshore.

Best Things to Do in the Hamptons

Chill out after a morning at the beach by strolling through the perfectly manicured gardens at Sagaponack's Madoo Conservancy. Established in 1967 by artist, writer, and gardener Robert Dash, this stunning space is like stepping into a fantasy dreamscape.

If the weather is less than beachy, head over to Bridgehampton's Scuttle Hole Road for Channing Daughters Winery's seated tastings (reservations are recommended). You can even make a whole day of it, stopping by Wölffer Estate Vineyard, in neighboring Sagaponack, for a glass of the winery's esteemed rosé, followed by a digestif at the South Fork's very own Sagaponack Farm Distillery.

Pick up a loaf of still-warm olive ciabatta at Carissa's Bakery (there are two East Hampton locations). And, of course, no trip to the Hamptons would be complete without dinner at East Hampton's decades-old celebrity magnet, Nick & Toni's (make your reservation in advance).