A World Away in Montauk

A World Away in Montauk

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

The Highest Standards in the Sky

The Highest Standards in the Sky

The pilot of a plane nearing O’Hare Airport announces its “final descent into the greater Chicago area,” and the grammar mavens on board all wince. The error there is redundancy—either “greater Chicago” or “the Chicago area” would suffice.

Adam Schaefer speaks in very literate English, but the Director of Operations for Tradewind Aviation might just shrug that one off. Not simply because Schaefer is a pilot, himself, but out of his deep bias toward what redundancy means for aviation safety.

“Redundancy in our business is everywhere you look,” he says. “We don’t even perceive it the way people outside the industry might, as something excessive or burdensome. To us it’s fundamental.”

In aircraft design the mechanical functions all have backup systems. In pre-flight protocols like the one Tradewind follows, a plane is inspected by mechanics, then by the pilots. “Our scheduling software has 100 validation checks,” says Schaefer, who is both a pilot and a licensed mechanic, “and those checks have double-checks.” Certain safety factors are the responsibility of a dispatcher, then a software programmer, then the chief pilot. “You see things caught at the third level,” Schaefer says. “It’s rare but it happens.”


The Federal Aviation Administration has two sets of regulations covering private aviation. Companies that fly scheduled routes as well as charters are held to higher standards than their charter-only counterparts. This two-tier arrangement plays out in everything from financial fitness to the seniority and experience level of inspectors, according to Schaefer. Nor does he question the premise.

“The idea, as I understand it, is that someone buying a single seat on a scheduled flight will feel less need for diligence and scrutiny than someone booking a charter,” Schaefer says. “Chartering planes is so relatively uncommon that people who do it will take steps to check things out on their own. Therefore, if your company offers scheduled flights the safety responsibility is more on you.”

Tradewind provides both scheduled and charter service because it’s a more efficient use of company assets and resources—a better business model, for the markets being served. That causes a higher set of safety standards to kick in, and the company would hardly seem to mind, because it actually goes one step further and subjects itself to monitoring by a third-party inspection service. And pays for the privilege.

That independent party is ARGUS International, recognized for its authoritative rating system for aircraft operators and their safety history. Tradewind participates in ARGUS CHEQ (which stands for Charter Evaluation and Qualification) and has attained the status of ARGUS Gold, indicating a safety history in the upper tier of the industry. “You provide them with a very extensive body of data when you register,” explains Schaefer. “ARGUS knows our pilots, our aircraft, the whole company, really. They produce an overall safety score for us based on a wide range of factors.”

Part of the double-check and triple-check culture at Tradewind involves monitoring the monitor, so to speak. Recently there was a tarmac accident that reportedly caused damage to a Tradewind aircraft. “That turned out to be incorrect, and a staff member at our operations center flagged it,” recalls Schaefer. “The plane involved had a similar tail number to one of our planes, and it was misidentified by a couple of digits. Within an hour the correction was made.”


The safety history compiled by Tradewind since it began operations is truly remarkable. The company has such a clean record that some combination of modesty and superstition might induce Schaefer not to talk about it. But either sentiment would cloud or obscure the patterns, standards, and procedures that a culture of safety is built upon.

“What we’ve done most recently to institutionalize our practices is develop and release our own, proprietary SMS, or Safety Management System,” says Schaefer. “Major carriers are required to do this, but we’ve chosen to do it on our own. It’s a way of moving farther up the timeline from what is considered an event and getting to the precursors—the circumstances that could lead to a problem down the line.”

Safety in the air is the product of endless small details. For every little fastener holding the plane together, there is a specification for its size, for the material it’s plated with, for the lubricant applied to its threads before torquing, for the torque (tightness) value, and a spec for where, in sequence, that particular fastener gets tightened.

But along with being exact and unyielding, safety aloft is also fuzzy, according to Schaefer. How is that?

“Safety is a feeling, it’s a general perception,” he says. “We find that the more people fly with us, the less they even think about safety.” Interestingly, safety practices at Tradewind extend to the purely cosmetic, such as cabin cleanliness and sharp-looking uniforms worn by the crew. “At some level of consciousness, people associate soiled carpeting and worn upholstery with low standards overall,” Schaefer says, “including a lax approach to safety. So, if we take great cosmetic care of the plane, it stands to reason we also take great mechanical care.”

He can say that again.

Flying LA to St. Barth: Tradewind Meets Clay Lacy

Flying LA to St. Barth: Tradewind Meets Clay Lacy

For discerning travelers en route to the Caribbean, the transfer between a large-cabin charter jet and a final-leg turboprop can often lead to inconsistencies in service. In response, Tradewind Aviation and large-jet operator Clay Lacy Aviation have partnered to provide seamless access to St. Barth, including plane-to-plane transfer averaging just 10 minutes. 

To provide a first-hand account of the service, we spoke with entrepreneur Mark Bonfigli, who owns two world-class aircraft managed by Tradewind and Clay Lacy, respectively, and regularly makes the transfer journey from Los Angeles to St. Barth:

“St. Barth is an amazing French island that has a great community,” says Bonfigli, who has been traveling to the Caribbean for both business and leisure for many years. “They are focused on delivering extreme, beautiful luxury and nature and some of the best food you will ever have.”

 Photo: Clay Lacy Aviation

Photo: Clay Lacy Aviation

Over the years, while chartering flights to the stylish destination, it quickly became apparent to Bonfigli that what was missing for travelers was two services that could work together. Because large jets cannot land at Rémy de Haenen Airport, passengers were stepping out of glamorous, high-end jets and into puddle-jumpers that made for bouncy flights with no air conditioning.

“There’s nothing wrong with that experience if that’s what you’re looking for,” says Bonfigli, noting the open windows on the flights. “But in reality, a lot of people are looking to not sweat and still be able to enjoy a glass of champagne.”

Once he had identified the disparity, an idea was born. “How do you put together a seamless travel plan for someone that’s coming from the US to high-end, luxury locations such as St. Barth?,” he asked. “That’s what SEXYjet and BabySEXY accomplish together. You get a luxury service all the way through.”

Bonfigli’s planes, a Gulfstream GV and Pilatus PC-12, are some of the most recognizable aircraft in the industry; the GV turns heads with a sleek, color-changing exterior that took more than 3,000 man-hours to complete (and the PC-12 will receive a similar paint job in the future).

 Photo: Clay Lacy Aviation

Photo: Clay Lacy Aviation

Inside the sumptuous jet, passengers are welcomed by elegant Italian-leather seats, lights that shift in color, and a premier entertainment system – along with a partitioned sleeping compartment in the back of the aircraft. The professional cabin server, Melissa, is at your service and caters based on your favorite foods. (For Bonfigli and his wife, this means organic, locally made guacamole and their favorite gluten-free chips to start.)

“It’s kind of dreamy,” says Bonfigli. “Everything is simple and super elegant and comfortable. It’s just so beautiful in there that you don’t really want a lot of flights to end so quickly.”

The decision to have Clay Lacy manage the jet was simple.

Founded in 1968 by the aviation icon of the same name, the experienced aviation company has flown world leaders (including six US presidents and a British prime minister), government agencies, professional athletes, celebrities, and more. They typically employ GV aircraft for flights like the one from LA to San Juan, Puerto Rico – where the transfer takes place – because of the jets’ exceptionally high cruising altitude, long range, endurance, and reliability.


Upon arrival in San Juan, the GV and PC-12 provide unprecedented convenience by parking next to each other on the runway. Passengers can change planes in just a few minutes without going through an airport terminal or lengthy customs process.

Says Bonfigli, “You literally get on the plane in LA, you walk on a red carpet between the two planes, and then you find yourself in St. Barth.”

Perfect for the shorter runway at Rémy de Haenen Airport, the Tradewind-operated PC-12 is a high-performance, jack-of-all-trades aircraft that still delivers exceptional comfort. Unlike most small planes from other operators, those managed by Tradewind offer two pilots – a key feature in making passengers feel comfortable when transitioning from a larger jet.

“For a small plane service, there’s no one that comes close [to Tradewind] in my opinion,” says Bonfigli. “I’ve flown all kinds of small planes all over the world, and I’ve never had such a positive, consistent, year-after-year experience. I think I’ve probably done 50 trips with them.”


His PC-12 in particular offers oversized reclining seats, a fridge for cool drinks and light snacks, and a lavatory. (It’s so comfortable that he has actually taken it on much longer flights from St. Barth to Miami twice.)

“The beauty of it is that we’re using a plane that’s in the top percentile,” he says, “and we’re beautifying it and making sure that we’re serving [passengers] the way that we were when they were on the big jet.”

On the island, a quick check-in with customs – about 10 seconds, according to Bonfigli – grants you access to ethereal beaches, lush rolling hills, and unmatched accommodations from five-star hotels to stylish villas. Bonfigli and his wife spend their days hiking the shoreline, indulging in the vibrant culture, and playing beach tennis with locals. (He actually owns a beach-tennis-inspired apparel and sporting goods company with innovative concepts like bags made from indestructible, carbon-fiber sailcloth.)

“Both Clay Lacy and Tradewind understand what we’re trying to deliver,” says Bonfigli of the journey to and from the island, noting that passengers can quickly clear US customs and change planes in San Juan on the return. “I think that’s what we’re offering: luxury that doesn’t really exist.”


Featured Image: Clay Lacy Aviation

The Story of Tradewind: A Spotlight on Eric and David Zipkin

The Story of Tradewind: A Spotlight on Eric and David Zipkin

“Our mother still doesn’t believe that we’re able to work together, because we spend so much time as rivals,” says Eric Zipkin, President of Tradewind Aviation.

He and his brother, Vice President David Zipkin, founded the company in 2001, building on a lifelong passion for aviation. Raised with an entrepreneurial mindset, the brothers had always known that they would work together and embarked on several ventures before identifying the need for high-quality, regional flights in the Northeast.

Both were private pilots at the time, and Eric was working for a charter company (a position he attributes to his wife, who said he should probably get paid if he was going to spend every day at the airport). After learning the ins and outs of the charter business, it didn’t take Eric long to determine that there was a niche opportunity waiting for them.

“When we first started,” he says, “if you needed to go from New York to Nantucket, the options were – put bluntly – not the greatest. They were small airplanes, not necessarily well maintained, very inconsistent quality standard.”


While larger jets (like those made by Gulfstream) offered a pampered experience for charter fliers, with luxe interiors and exceptional service, the options were very limited for small aircraft. The planes available for travel to Nantucket and similar destinations were outdated, and many offered only a single pilot.

“We used better airplanes,” says David of the company’s first charter flights. “Two pilots, full service, just like you would in a big jet.”

And it wasn’t long after inception that Tradewind clients began asking if they could share a flight, only needing one or two seats each. The Zipkins said absolutely, and the idea for scheduled shuttles with single seat purchase was born.

“That was really the big break,” says David. “That’s where it turned into something that was accessible to a larger portion of people, because it’s a lot cheaper, of course, to buy one seat on a charter plane than the entire plane. The word really got out. One plane turned into two planes turned into three planes, and the rest is history.”

The company expanded to various destinations in the Northeast and Caribbean, with the favorite for both brothers being St. Barth, hands down. A challenging approach – which they will tell you brings out the best in pilots – and the culture of the island itself make it a memorable place to land again and again. (During a stay, David recommends enjoying the secluded Saline Beach, kite surfing Grand Cul de Sac, and indulging in some of the island’s world-renowned cuisine.)


Today, Tradewind flies 30 to 40 flights to Nantucket alone on a summer day, along with any number of flights to other shuttle and charter destinations. Approximately 70 percent of the flights are shared, and the other 30 percent are private. But with any one of Tradewind’s flights, you will find the quality of service to be the same.

“We are an airline,” says David, “but we consider ourselves more of a charter company than we do an airline. Because everything we do with our scheduled flights is done with an eye for private charter – asking ourselves what would someone expect from a private charter and trying our best to deliver that on an airline flight.”

Throughout the journey, both Zipkins will tell you that the most memorable experiences came during times of struggle – like in the fall of 2017 when Hurricane Irma decimated Puerto Rico, St. Barth, and the surrounding islands.

One day after the storm, Eric and David were in the Caribbean coordinating much-needed relief flights and evacuating visitors and islanders. And St. Barth recovered quicker than anyone could have imagined. David attributes the restoration to the incredible spirit of the people, saying, “In just a short five months or so – besides some of the hotels that are still closed – they’ve really recovered almost completely.”


Tradewind’s efforts in Puerto Rico and St. Barth closely mirrored another natural disaster years before: the devastating earthquake in Haiti in 2010. “We were delivering relief supplies, landing on a closed road in rural Haiti right at the epicenter of the earthquake,” says Eric. “It’s always good to feel like you’re having an impact, that you can do something.”

“We were in a position to help people who didn’t have anything,” adds David, “and that was really, really rewarding.”

Looking to the future, the Zipkins only see continued expansion for Tradewind in both the Northeast and Caribbean. The concept of high-end, premium short flights is one that would work in many places, they will tell you, as they note the possibility of shuttles to Newport, Montauk, and Cape Cod as well as additional Caribbean islands.

“We’re really looking at an exciting summer season going forward,” says Eric. “We’re looking at a lot more flying and a lot more opportunities for growth.”

Eric and David both joke that running the company together only works because they are only in the same room every two weeks or so, but they also speak about the implicit trust between family. “[The] rivalry bleeds through from time to time,” says Eric. “But more importantly, you know you’re working with someone that always has your back. There is never, ever any question about that.”

3 Caribbean Islands Ideal for Your Next Family Getaway

3 Caribbean Islands Ideal for Your Next Family Getaway

Blending tranquil stretches of white-sand beach with inspiring history, watersports, and spacious villas, few vacation destinations are as attractive for families as the beautiful Caribbean islands.

Whether you’re seeking adventure, relaxation, or both, these three islands, in particular, offer an array of experiences suited for all members of the family, and each is easily accessible with Tradewind’s regularly scheduled shuttle flights and private charters.



Regarded as one of the top sailing destinations in the world, Antigua is known for its ethereal beaches and enchanting historical sites like Nelson’s Dockyard National Park.

Set on four and a half miles of pristine shoreline, Jumby Bay Island welcomes families with an incredible collection of private villas just off the coast of mainland Antigua. And across the main island, Carlisle Bay offers elegant two- and three-bedroom suites and extensive children’s programs framed by verdant rainforest and calm Caribbean seas.

Both resorts serve as jumping-off points for sailing lessons with Ondeck, diving among vibrant coral reefs, and swimming with Southern Stingrays in Stingray City’s interactive eco-tour. On shore, families will find endless opportunities for exploration in natural wonders like Devil’s Bridge and the Pillars of Hercules, the pastel-colored local villages along Fig Tree Drive, and the museum and grounds at Nelson’s Dockyard, which is a beloved UNESCO World Heritage Site.

For family-friendly dining, head to Catherine’s Café to indulge in exceptional French cuisine overlooking Pigeon Beach at sunset.


 Photo: Four Seasons Resort Nevis

Photo: Four Seasons Resort Nevis

A serene escape that feels entirely removed from the rest of the world, Nevis captivates families with its secluded shorelines encircling the towering Nevis Peak. Along with beaches and lush rainforest, the island has a distinct element of history with its 17th- and 18th-century sugar plantations – some of which have been restored as luxury hotels.

In the green foothills of Nevis Peak, The Little House at Montpelier Plantation & Beach offers two elegant bedrooms and an abundance of Old World charm throughout its century-old structure, while on the edge of the sea, Four Seasons Nevis features luxurious multi-bed guestrooms and one- to seven-bedroom villas with private pools. (The five-star resort also has the Kids for All Seasons program for children and the option of a fully stocked villa kitchen upon arrival.)

Spend your days visiting historic attractions like Hamilton Estate and snorkeling among the vibrant reefs of Herbert’s Beach. In the late afternoon or evening, stroll Pinney’s Beach to choose from an array of rustic restaurants and sip cool drinks while the kids enjoy the playground at Sunshine’s Beach Bar.

St. Barth

 Photo: Antoine Verglas, courtesy of Eden Rock

Photo: Antoine Verglas, courtesy of Eden Rock

Traditionally known as a destination for couples on glamorous escapes, St. Barth is equally suited for families traveling with children. Beaches like Grand Cul de Sac offer calm, shallow waters (with a protective reef circling the bay), and any number of active pursuits from hiking to kite surfing beckon.

Those visiting St. Barth in mid-2018 will find a sumptuous private villa to be the best option, as many of the island’s luxury hotels are still undergoing renovations following last year’s Hurricane Irma. (The island has returned to its quintessential glamour with most restaurants and shops having reopened and annual events going on as planned.) Closer to the holidays, completely restored resorts like Eden Rock, Le Guanahani, Cheval Blanc, Le Toiny, and Le Barthélemy will be open.

The youngest travelers in your group will enjoy sites like the Inter Oceans Museum with more than 9,000 shells from all over the world, while all will delight in snorkeling amongst leatherback sea turtles in Grand Cul de Sac, boating to the iconic Colombier Beach, and indulging in world-class cuisine in Gustavia and beyond. (Try L’Isoletta for thin-crust pizza on the harbor and Sand Bar or Indigo on the Beach for spectacular ocean vistas.)

During your stay, make sure to charter a sailboat for a day to circle the island and watch the brilliant sunset over the Caribbean Sea.

From the Cockpit: 6 Destinations Recommended by Tradewind Pilots

From the Cockpit: 6 Destinations Recommended by Tradewind Pilots

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.


Want to fly for Tradewind? Click here to view our open pilot positions and apply.