Between its white sand beaches, vibrant Atlantic sunsets, and buzzing social scene, there’s no place quite like the Hamptons for a long-weekend getaway. Here, New England beach town charm meets urban sophistication, long-time locals mingle among celebrity homeowners, and city dwellers are in good company as they escape the metropolitan bustle for a few days to savor the stylish serenity of this Long Island haven.

There’s something for everyone among the 20 or so distinct villages in the Hamptons, each with its own personality. Visitors will find both laid-back, countryside-inspired hideaways on the beach and lively destinations filled with five-star restaurants, shopping, and nightlife.

With so much to discover, bypass much of the oft-maligned city traffic and fly directly into the Hamptons to spend more time enjoying what makes the East End such a beloved retreat. Tradewind offers charter flights to East Hampton Airport, Montauk Airport, and Westhampton Beach Airport, all providing convenient access to the Hamptons’ top towns.

After your flight touches down, experience the best of the area with this 72-hour Hamptons itinerary.

Day One

Begin your getaway in East Hampton, one of the area’s most popular hamlets and a hub for some of the East End’s best dining, shopping, and nightlife. After renting a car (or hiring a car service), check into The Baker House 1650, a luxury inn within walking distance of the main town and beach. While the Hamptons is known for summer-long rentals and vacation homes, upscale bed and breakfast-inspired accommodations like these offer an alternative for weekend visitors, providing a taste of a historic Hamptons home stay with the amenities of a high-end hotel.

Photo: The Baker House 1650

Photo: The Baker House 1650

Spend some time settling into The Baker House 1650 to enjoy the property’s 17th-century architecture, lush grounds, and three pools, then wander down Main Street to explore East Hampton’s shops. You’ll find both classic outposts and high-end boutiques, from chic swimwear at Vilebrequin to your next beach read at the ever-charming BookHampton

Photo: BookHampton

Photo: BookHampton

After a bit of retail therapy, head toward Bridgehampton for an early afternoon reservation at the tasting room at Wölffer Estate. Perhaps best known for their aptly named Summer in a Bottle rosé, guests can sample a variety of wines alongside gourmet small plates and charcuterie boards, all set to sweeping vineyard views.

After your afternoon of wine tasting, make your way to Bridgehampton’s lively Main Street to wander among shingled buildings and boutiques. While you’re there, those interested in dessert before dinner should stop by the iconic Candy Kitchen, lauded throughout the Hamptons for their decadent homemade ice cream selection.

Make a reservation ahead of time for dinner at Jean-Georges at Topping Rose House, crafting contemporary farm-to-table cuisine in one of the Hamptons’ most elegant hotels. The famed chef’s menu sources local ingredients from the area’s farmers and fishermen, as well as produce grown on the property’s one-acre farm.

Day Two

Begin your day with a workout at one of the Hamptons’ many trendy fitness studios — SoulCycle, Flywheel, AKT, Erika Bloom Pilates, and Tracy Anderson all have outposts in East Hampton, or you can take a class at Barry’s Bootcamp in nearby Amagansett. For a lighter activity, head over to the East Hampton Main Beach on one of The Baker House 1650’s bikes for rent, then kick your shoes off for a morning walk on the sand.

Photo: Dr Smood

Photo: Dr Smood

Refuel with a green juice at health-conscious café Dr Smood in East Hampton, then take a short drive north to the town of Sag Harbor. As an old whaling town, quaint colonial-era architecture lines the main street and smaller, family-run shops triumph over big-name brands.

For lunch (or brunch) after a stroll through the town, enjoy panoramic harbor views paired with locally sourced dishes at The Restaurant at Baron’s Cove. Beautifully renovated in 2015, Baron’s Cove is known by many as Sag Harbor’s most stylish hotel, offering sleek beach house-inspired design, a saltwater pool, and a happening lounge and dining scene. If you find yourself in Sag Harbor later in the evening, you can also sit down for dinner on the water at local favorite Beacon, open only during the summer.

Photo: Baron’s Cove

Photo: Baron’s Cove

Otherwise, make your way back to East Hampton for an afternoon of R&R. Unwind by the pool or at the spa at The Baker House 1650, or take your bike back to the beach, reveling in the relaxed pace of Hamptons living. For dinner, make a reservation at Hamptons mainstay Nick & Toni’s, offering rustic Northern Italian cuisine in a farmhouse setting (that’s also likely playing host to at least a celebrity or two on any given night).

Day Three

Though spending free time at one of the Hamptons’ many beaches is highly encouraged throughout your entire stay, dedicating a few uninterrupted hours to lounging out on the sands is a must. The Baker House 1650 offers East Hampton Main Beach parking passes to guests (which are required), as well as umbrellas and chairs to unwind on. But first, stop by Cavaniola's Gourmet in Amagansett for all the fixings of a perfect beach picnic, from cheeses to paninis (it’s one of chef Ina Garten’s favorite local stops).

Photo : Section215 via Flickr / CC BY

Photo: Section215 via Flickr / CC BY

In the afternoon, take a drive up to Montauk. This fishing village has become a Hamptons hotspot in recent years, seeing an influx of dining, nightlife, and hospitality offerings. Fondly referred to as “the End of the World,” Montauk is perched on the easternmost tip of Long Island, and its expansive Atlantic views are best seen from the historic Montauk Lighthouse. Climb 137 iron steps for a high-up vantage, or find a perfect spot on the grounds to frame a picturesque lighthouse photograph.

Because no trip to the Hamptons is complete without a decadent lobster roll, stop at the eponymous Lobster Roll in Amagansett on your way back, commonly referred to as Lunch thanks to its iconic glowing sign. There’s little argument over its status as the best lobster roll in Long Island (if not one of the best in the world). As the sun dips into the Atlantic, it’s the perfect way to cap off an idyllic weekend in the Hamptons.

Photo: The Lobster Roll

Photo: The Lobster Roll

Featured photo: Sue via Flickr / CC BY


Tradewind offers private charter flights to East Hampton (HTO), Montauk (MTP), and West Hampton Beach (FOK) year-round. To reserve a charter, call us at 1-800-376-7922 or click here.