Explore the Hamptons: Beach Paradise with Stunning Wineries and 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. Moreover, 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.

Consequently, 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, influencing your decision on where to stay. If you’re seeking a laid-back, surfer experience, the towns to the east may suit your style: East Hampton, Amagansett, and Montauk feature beautiful beaches, excellent restaurants, and a more relaxed atmosphere. Meanwhile, Springs continues to be an under-the-radar destination for those seeking less crowded bay beaches and superlative sunsets.

On the other hand, Southampton, to the west, includes the hamlets of Bridgehampton, Sag Harbor, Sagaponack, and Southampton Village. If you’re after a more formal Hamptons experience, this side offers old estates, galas, and polo matches that are typical of the area. If this sounds like your ideal getaway, raise a glass to all things Southampton.

What about Westhampton Beach? This village lies to the west of the Shinnecock Canal and is not officially considered part of the famous Hamptons. However, it boasts an impressive array of beachfront mansions along Dune Road. Westhampton’s shops, restaurants, and beaches provide ample reasons for a visit if you’re looking to get close.

Where to Stay in the Hamptons

For a unique lodging experience, Montauk’s Crow’s Nest is highly recommended for its bohemian decor, twinkling Edison bulbs, and stunning views of Lake Montauk at sunset, embodying hotelier Sean MacPherson’s surf-centric vision. The hotel features a mix of rooms and cottages adjacent to its beloved Mediterranean-style restaurant, thriving from May through September.

Further west, the 15-key Roundtree in Amagansett offers a boutique experience where guests can explore the property alone or with pets (the hotel is pet-friendly). Beach bonfires, cooking classes, trips to local wineries, and guided walking tours are all signature experiences that promise 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, along with an incomparable view of the water. Open year-round, this property ensures that there’s not a bad time to visit.

Best Beaches in the Hamptons

When choosing where to spend your sun-soaked days, it often comes down to personal preference. If you’re not local to the Hamptons, there are several options for paid day parking lots. Cooper’s Beach, in Southampton, is a wide and long beach with ample amenities and a spacious lot.

In Sag Harbor, Foster Memorial Beach (also known as Long Beach) is perfect for swimming in shallow, calm waters. It is a public beach and offers easy access.

Amagansett’s Atlantic Avenue Beach features public access, lifeguards, concessions, and restrooms, in addition to an active surf break. Finally, in Montauk, Kirk Park Beach boasts a pay lot that provides restrooms and a scenic hike over beautiful dunes, where, during the summer months, lucky visitors might catch whales breaching offshore.

Best Things to Do in the Hamptons

Relax 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 remarkably reminiscent of a fantasy dreamscape.

If the weather isn’t ideal for beach activities, consider visiting Channing Daughters Winery on Scuttle Hole Road for delightful seated tastings, where reservations are encouraged. Additionally, you can easily spend a day exploring, starting at Wölffer Estate Vineyard for a glass of their esteemed rosé, then enjoying a digestif at the Sagaponack Farm Distillery.

Finally, don’t forget to visit Carissa’s Bakery (with two East Hampton locations) for a loaf of freshly-baked olive ciabatta. Furthermore, no trip to the Hamptons would be complete without dining at East Hampton’s decades-old celebrity favorite, Nick & Toni’s — remember to plan your visit in advance.