A breathtaking landing on the edge of the Caribbean may define a place for one pilot, while another could be drawn by unforgettable cuisine with a view of the Rocky Mountains. From seaside escapes to late winter respites, here are six favorites from our pilots at Tradewind, along with tips for how to get there and what to do once you arrive.

Hilton Head, South Carolina


Abundant in history and natural beauty, Hilton Head is a coastal sanctuary set along 12 miles of scenic beaches. There’s nothing challenging about landing on the island in a Pilatus PC-12 – in fact, it’s the panoramic views that make the destination a favorite among pilots. Landing in a Citation CJ3 requires finesse, but you wouldn’t know it as expertly trained pilots transition effortlessly from sky to runway.

After landing, head to The Westin Resort & Spa. The Atlantic is just steps from your retreat, along with nearby preserves for horseback riding, moss-covered bike paths, and premier golf courses. Dinner takes you to The Jazz Corner for award-winning live music and Southern flavor, Michael Anthony’s Cucina Italiana for truly authentic Italian cuisine, or the pilots’ choice for fresh-off-the-boat fare, Hudson’s Seafood House on the Docks. (Assistant Chief Pilot Stephen Pustola says, “Get the blackened shrimp, hush puppies, and finish it with some key lime pie.”)

How to Get There: Charter a flight with Tradewind to Hilton Head Airport (HXD).

St. Barth


“No two landings are the same on St. Barth,” says Pilot John Hepple.

He’s hardly alone in his perspective, with countless aviation enthusiasts recalling the beauty of that perfect landing on the exclusive Caribbean island. Both challenging and rewarding, St. Barth has a short, 650-meter runway capped at either end by mountains and sea. But with a versatile aircraft like the Pilatus PC-12, the breathtaking touchdown is made incredibly safe.

“Stick and rudder, this is the ultimate experience,” says Pilot Derek Schwalenberg. “2,100 feet on a downslope over an obstacle, and there is beautiful terrain around.”

After making your spectacular arrival on St. Barth, ethereal white-sand beaches and stylish hideaways beckon. Stay in one of the island’s most sought-after villas while you hike to Colombier Beach, shop designer boutiques, and indulge in extraordinary French cuisine from the likes of Le Tamarin or Jean Claude Dufour’s L’Esprit. Make sure to stop into the street-food-inspired 25 Quarter too, a favorite among pilots who are always made to feel at home.

How to Get There: Fly Tradewind’s scheduled shuttle to St. Barth (SBH) from San Juan or Antigua, or private charter from Puerto Rico or the US Virgin Islands.

Aspen, Colorado

 Photo: AspenSkiingCompany

Photo: AspenSkiingCompany

Set some 8,000 feet above sea level in the magnificent Rockies, Aspen is one of the world’s most iconic mountain resort destinations. Whether blanketed in snow or verdant green in summer, the luxury retreat is a top choice for pilots for its stunning landing in bowl-like surroundings and outdoor pursuits from skiing to hiking.

“There is so much to do in the mountains in the winter,” says Assistant Director of Operations and Pilot Nickolaus Ogle, “but I particularly enjoy the summers in Colorado because of all of the great hiking, golfing, and biking.”

Landing at Aspen Airport comes with an array of unique challenges that make it a memorable destination for pilots, from the quick descent to the unpredictable winter weather. Once on the ground, indulge in five-star accommodations at The Little Nell or St. Regis, and visit Ogle’s favorite gourmet sandwich shop, White House Tavern.

How to Get There: Charter a flight with Tradewind to Aspen-Pitkin County Airport (ASE).

Nantucket, Massachusetts

 Photo: Bobak

Photo: Bobak

New England coastal charm abounds in Nantucket, an idyllic island defined by serene beaches and towering lighthouses. In the quaint villages, you will discover exquisite cuisine from standouts like The Pearl and Straight Wharf, as well as spectacular theatrical performances at Dreamland Theater.

“At Nantucket, you never really know what to expect as far as visibility,” says Hepple, who welcomes the always memorable journey to reach the tranquil island. “The weather literally changes by the minute."

Reserve a waterfront room at White Elephant for your stay, and afterward, consider hopping a quick shuttle to Martha’s Vineyard for equally stunning coastlines.

How to Get There: For trips in March, charter a flight with Tradewind to Nantucket Memorial Airport (ACK). Tradewind’s scheduled shuttles to Nantucket begin in April.

Stowe, Vermont

One of the most famous ski resort towns in the East, Stowe invites long days on the slopes during winter and fly fishing, zip lining, and hiking in summer. “Even if you don’t hit the slopes,” says Schwalenberg, “there are quaint cider mills, the Ben & Jerry’s ice cream factory, [and] local ice sculpting events.”

The landing into the Stowe Airport is smooth on VFR days, in which conditions are clear enough for pilots to visually see the descent, whereas IFR days, where instruments are relied upon, can be more interesting. “Often the weather up in the mountains is much different than it was even before you departed the New York City area,” says Schwalenberg. “It changes that quickly.”

After landing, take up luxury accommodations at Stowe Mountain Lodge no matter the time of year. The only ski-in, ski-out resort in Stowe is also a favorite home base for warm weather adventures.

How to Get There: For trips in March, fly Tradewind’s scheduled shuttle to Morrisville-Stowe State Airport (MVL). Afterward, charter a flight with Tradewind.



One of the most underrated destinations for pilots, Nevis is characterized by serene beaches, verdant rainforest, and an array of historic plantations and sugar mills. The island is much less frequented than adjacent destinations and offers a true escape for both travelers and pilots.

“The view of the stars is incredible at night,” says Schwalenberg, reminiscing on an evening landing – complete with a good crosswind and a shear zone about 50 feet above the runway, although the Pilatus PC-12 handles it beautifully.

While on the island, plan to stay at the intimate Montpelier Plantation, on the beach at Nisbet Plantation Beach Club, or the exquisite Four Seasons Resort Nevis – Schwalenberg’s personal favorite. He also recommends Indian Summer and Sunshine’s Beach Lounge for exceptional Indian and Caribbean cuisine.

How to Get There: For trips through April 9, fly Tradewind’s scheduled shuttle to Vance W. Amory International Airport (NEV). Afterward, charter a flight with Tradewind.


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