Compared to the bustle of New York City, some 110 miles away, Montauk really does feel like another world. The bohemian-chic neighbor of The Hamptons is home to beautiful Atlantic seascapes and stylish villages straight from your summer dreams, yet it is completely accessible for quick getaways or weeklong retreats with Tradewind's on-demand private charter flights.

Perched on the outermost tip of Long Island, Montauk spans from the village of Napeague in the west to the burgundy-and-white Montauk Point Light in the east – encompassing 13 miles of beaches flecked with quaint bed and breakfasts, upscale restaurants and boutiques, trendy beach clubs, and a flourishing new arts scene.

Touch down at Montauk Airport, where the relatively short runway cannot be accessed by larger jets but makes for an easy landing in a Pilatus PC-12. Then, whether you envision yourself sailing the coastline or dining on the freshest catch, here are our best recommendations for how to spend your getaway:

Where to Stay

During the summer, you have several choices in which to unwind at the end of a beach day. The most famous is Gurney’s Montauk Resort & Seawater Spa, a landmark inn boasting 2,000 feet of pristine shoreline, elegant guestrooms and beachfront cottages, the Seawater Spa with a one-of-a-kind, ocean-fed saltwater pool, and the lively Beach Club. (It’s also Montauk’s only year-round resort.)

Photo: Gurney's Montauk Resort & Seawater Spa

Photo: Gurney's Montauk Resort & Seawater Spa

For yachting enthusiasts, there is no place better than the iconic Gurney’s Montauk Yacht Club & Resort. The historic property – which recently underwent a multimillion-dollar renovation – overlooks the azure waters of Lake Montauk and offers a 200-plus-slip marina with plenty of opportunity for world-class sailing and fishing. And for more modern vibes, check out the stylish Montauk Beach House downtown. Known for its cozy, poolside fire lounge, the boutique hotel hosts a variety of upbeat events in season from fashion shows to DJs to pop-up shops.

Photo: Gurney's Montauk Yacht Club & Resort & Marina

Photo: Gurney's Montauk Yacht Club & Resort & Marina

Where to Dine

Waterfront views and fresh coastal fare await in the midst of Montauk’s vibrant culinary scene. Start your day at Joni’s Kitchen, a beloved local eatery with an easy ambiance. While you indulge in breakfast wraps, globally inspired pressed sandwiches, and fresh fruit smoothies, take in the array of vintage surfing photos on the walls – or take your breakfast to go to enjoy on the beach.

The setting is distinctly nautical at Duryea’s Lobster Deck with lobster crates decorating the bar and spectacular vistas of Fort Pond Bay beckoning on the deck. Bite into a much-acclaimed lobster roll for lunch or one of many other high-quality seafood choices like the Montauk Pearl Oysters.

Photo: Doug Young, courtesy of Duryea's Lobster Deck

Photo: Doug Young, courtesy of Duryea's Lobster Deck

Dinner takes you to the lush gardens of Arbor. Surrounded by greenery, the Mediterranean wine and beer bistro offers pan-seared scallops, grilled Spanish octopus, bouillabaisse, and other delectable entrees in an elegant atmosphere. For lighter fare, head to Swallow East on the harbor. You can share savory small plates of burrata, steamed clams, or tuna poke in an intimate setting with friends and family.

What to Do

Upon touching down in Montauk, your first destination should be the beach. With more than 5,000 acres of public beaches and parkland, the easternmost part of New York state abounds with natural beauty – from shorelines framed by rolling sand dunes to incredible, 70-foot-tall bluffs. Swim at Hither Hills State Park beach, hike the trail at Amsterdam Beach State Park to reach a secluded surf spot with great waves, or sip drinks in a breezy beach club.

Next, head to Montauk Point Light, the fourth oldest active lighthouse in the country, for sweeping views of the bluffs and the Atlantic. Closer to town, you will find pursuits for every interest from cycling to horseback riding to golfing – as well as a spectacular array of boutiques. Stop into Kailani (Hawaiian-inspired resort wear) or Montauk Dazies (designer styles) to pick up something to remember your time in Montauk.


To reserve a private charter flight with Tradewind, call us at 1-800-376-7922 or click here.


*Featured Photo: Gurney's Montauk Yacht Club & Resort