An Escape to Block Island

An Escape to Block Island

Only 13 miles of Atlantic Ocean separate a bubble of nearly autonomous New England charm from mainland reality.

With its white-sand beaches, towering bluffs, and glacier-carved hillsides speckled with colonial cottages, Block Island is completely walkable, stretching just 7 miles at its longest and 3 at its widest. Hovering below the radar of other, more spot-lit destinations of the Northeast, this storied enclave offers a Victorian-style escape, just a quick whisk away on a Tradewind on-demand charter flight.   

From quintessential coastal retreats to hikes along Block Island’s distinctive shoreline, here are our top recommendations to make the most of your getaway from the first minute you touch down and inhale the bayberry and salt air.

Where to Stay

 Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

Due to regional governance, Block Island remains one of the few places in the modern world that keeps corporate conglomerates marooned on the mainland in favor of local mainstays. The area’s innate resistance to chains extends well past coffee shops and fast food. Much like Block Island’s overarching essence, its locally-owned hotels afford guests an opportunity to delve back into the mid-19th century.

There’s Hotel Manisses, a renovated boutique replete with claw-foot tubs and other Victorian-era antiques, sitting seaside and piped with white-trimmed porches perfect for gazing at the shifting Atlantic. While there is no shortage of inspired eats on the island, Manisses houses its own renowned restaurant showcasing the very best in local seafood.

Then there’s the 1661 Inn, another beloved boutique hotel just down Spring Street whose flower-flecked open patios and sloping lawns greet the vast ocean to the east. It’s not just the Inn’s distinct ambiance that invokes notions of old-time Northeast; it is home to an acclaimed New England buffet breakfast—complete with locally-caught baked bluefish, omelets, pastries, pancakes, and of course, champagne.

Because the area’s hotels are family-owned, they usually offer an underlying bonus to visitors. By fostering inherent local connections, they can help guide itineraries or spontaneous adventures true to the steadfast spirit of the community—making an Atlantic getaway all the more immersive.

Where to Eat

 Photo: Winfield's Restaurant

Photo: Winfield's Restaurant

At first glance, Eli’s seems like a house plucked and placed from another whimsical era. Considered off-the-beaten-path from the island’s main attractions, this quaint eatery has been a local favorite since 1994, when it started offering Asian-inspired comfort food with upscale service and presentation. Eli’s seasonally-shifting menu offers everything from marbled-cut Bavette bistro steak to Nicoise-style seared tuna to an old-fashioned root beer float.

Just a few hundred feet to the northwest, Winfield’s Restaurant provides an informally cozy yet traditional setting in which to enjoy fresh seafood and local produce. “Simple elegance” is how Chef Berke Marye describes his Southern twist on haute cuisine, though you’ll find unmistakable hints of Italian, new American, and Asian influence in his island-inspired dishes as well.

For a spectacular dinner setting, the Atlantic Ocean backdrop of the Spring House Hotel can also be enjoyed from its charming in-house restaurant, which serves succulent dishes made from local meats and fresh sea catches, along with fruits and vegetables grown in its very own garden.

What to Do

 Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

With 40 percent of the island set aside for conservation, there’s a reason why its sprawling seaside plains and windswept hills boast some of the most treasured island hikes and birdwatching on the planet.

The island’s seven nature trails add up to 25 total miles which can be explored via hike, bike, or horseback. Each one highlights a unique perspective of wildlife or ocean view—like Clay Head Hill Trail, which rambles along dramatic bluffs on the northeast shore to finish at the historical marker and sunset vantage dubbed Settlers’ Rock.

Lighthouse aficionados will find two attractive beacons on Block Island. Less than a half mile from Settlers’ Rock, the octagonal tower of North Light stands sentinel to the Atlantic tide. On the south side, raised 200 feet above the ocean on the Mohegan Bluffs, stands the red-bricked and architecturally-refined Southeast Light.

 Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

While the island is nearly surrounded by beaches—17 circuitous miles of them—a few are worth mentioning above the rest.

Fred Benson Town Beach provides the most traditional beach setting on the island, complete with pavilion, lifeguard patrol, bathrooms, concession stand, and rentals. Some, however, may want to pursue a more private stretch of sandy coast, and to find it they only have to venture north.

There you’ll find Scotch Beach, where white sands and few rocks set the ideal stage for body surfers and body boarders to ride the tide. Even further north lies Mansion Beach. Named for a burned-down manor and farthest away from town, it’s generally known for clearer waters, smaller crowds, and even larger waves.

Its undulating landscape blending seamlessly into sea and sky, Block Island remains one of the few places where you can start your day with a stunning sunrise on the eastern shore, bask in an island daydream all but lost in time, and bookend it all with a beautiful sunset on the western coast.


Featured Photo: Block Island Tourism Council

A Life in Cinema, Split Between New York and Nantucket

A Life in Cinema, Split Between New York and Nantucket

In anticipation of this year’s Nantucket Film Festival, accessible by Tradewind with daily scheduled flights and private charters to the island, we sat down with Executive Director Mystelle Brabbée to talk past, present, and future of the acclaimed film showcase.

In the Oscar-nominated 2015 film Brooklyn, a young Irishwoman walks New York streets longing for the salt air and village life of her childhood in County Wexford. In the spirit of movies, storytelling, drama, and character, it’s easy to ascribe similar romantic yearnings to Mystelle Brabbée – needing only to substitute windswept Nantucket for Enniscorthy, Ireland.

A Brooklyn resident herself, Brabbée has been executive director of the Nantucket Film Festival since 2012, and she’s curated the festival program for a total for 16 years. Blond and athletic-looking, with a style both humble and intense, Brabbée annually spends the last week of June like the main character in the final reel of a blockbuster action flick, striving for all manner of happy endings as a year’s preparation unspools over six exciting days.


Plenty of New Yorkers split time between the city and Nantucket, but do any of them bring their work out to the island in such a climactic – not to mention high-pressure – fashion? It seems not, and as the late spring days keep NFF staffers working late, Brabbée falls into a mood akin to what Emerson must have felt when he wrote that “the air of Nantucket comes into your face and eyes as though it were glad to see you.”

In the run-up weeks before this year’s 23rd edition of the event, she indeed confessed to a bout of Nantucket fever. “It’s the same every year at this time,” she says. “I can’t wait to walk away from this desk, leave the city behind, and get out to the island.”

Its physical beauty and sensory effects were a revelation when Brabbée first visited Nantucket, during college. “I grew up in Colorado, and at the time I was studying at NYU, so I had never seen anything like it,” she says. “There was a sweetness and softness to the air that was all new to me.” As others have reported, she experienced the odd sensation of standing on solid ground yet feeling she was far out at sea.

If you’re an enthusiastic moviegoer and have not yet attended this festival, make a note to do so. The brother-sister duo of Jon and Jill Burkhart founded it and have guided the operation through nearly two dozen seasons, with Brabbée’s competence giving them an opening to step back. “For a festival of this prominence to be family-operated is unique,” Brabbée notes. “Over the years I guess I became part of that family, which extends to all our patrons and our filmmakers, too.” And indeed she did become an honorary Burkhart, according to Jill, who first hired Brabbée as a volunteer and soon offered her a staff role in programming.


“Mystelle said yes to my offer and we just went from there,” Burkhart says. “She is the longest-tenured staff member of NFF, and that’s owing to her combination of talent and knowledge – and especially to her passion. I sleep easy at night knowing she’s there running the show.”

Many of the moviemakers premiering their work on the island have returned again and again, including writer-director Debra Granik (Down to the Bone and the Oscar-nominated Winter’s Bone). “Debra’s entire career has been connected to and supported by our festival,” says Brabbée. “That’s one of the great things about being around so long.”

Few, if any, film fests are as inviting and walkable as Nantucket. And while it’s not the only such event with a heavy schedule of forums and presentations, it can claim a particularly inclusive mood to its programs. “This year we’re taping live with National Public Radio – their “Ask Me Another” Saturday show,” says Brabbée. “We’ll also have a Q&A session with Noah Baumbach, Adam Driver, and Ben Stiller.” If you’re attending for the first time, you will surely relish the anybody-can-talk-to-anybody atmosphere this gathering fosters.

The Burkharts, who as kids moved to Nantucket from (where else?) Brooklyn when their parents made a somewhat impulsive lifestyle reboot, envisioned a festival atmosphere in keeping with the island’s high-season escapism. “From the beginning, we likened it to summer camp,” recalls Jill Burkhart. “All it needed to succeed was people who love film, love this place, and want to share the intimacy and the storytelling.”


She recalls a night during year three when a young filmmaker screened his movie, spoke with audience afterward, and noticed one couple particularly taken by the film and its auteur both. “It so happened he’d never had a lobster dinner, and these folks said they had to fix that, so they took him out for lobster,” she says. “That wouldn’t happen at Sundance or Toronto or any big-city festival.”

Historic preservation is tantamount to a religion on Nantucket, dating back to the 1950s and Walter Beinecke Jr., who was heir to the S&H Green Stamps fortune and a devotee of classic island architecture and anti-commercialism. When the festival celebrated its 20th anniversary, Brabbée and her team sketched a design for classy-looking canvas signs that would hang from street lamps throughout the town’s cobblestone-paved center. They were informed that their signs were, ahem, against ordinances.

“The NFF is a commercial enterprise, so we’ll come up with plans and ideas that any business would,” says Brabbée. “Now and gain we run into prohibitions. The same preservation ethic that keeps the island so pristine can derail some of our plans. You learn to adjust.”

Asked to search through her long tenure and find a few festival moments that stand out, she at first stumbles, as too many memories flood in. Then she recounts the screening of Life, Animated, an award-laden documentary based on a father’s account of his autistic son’s obsession with Disney animated films – and how that fixation became a doorway for the boy’s dramatic progress in regaining speech and other capacities.


The filmmaker, Roger Ross Williams, provided background on the story and its central figure, Owen Suskind. Also in attendance was renowned composer Stephen Schwartz, author of so many familiar tunes in the Disney animation songbook. “Stephen played, and as he did the boy got up on stage and sang,” recalls Brabbée. “We plan and prepare all year, then something amazing will happen on its own.”

When the last ferry sails and the last flight out departs, ideas for the next year’s festival can begin to percolate. “Our fundamental value, the thing that guides us,” Brabbée says, “is the importance and the craft of storytelling – and in fact the joy of it.”

That idea resonates from Brooklyn to Nantucket and surely around the world. On occasion, like the evening a profoundly autistic boy stepped onstage to sing, the story will unfold right in front of you.


The 23rd Annual Nantucket Film Festival will be held June 20 – 25.


All photos courtesy of the Nantucket Film Festival.

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.”