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On the western edge of Massachusetts, Berkshire County stretches north-south for 60 miles, from the Vermont border to the Connecticut state line. Its vast beauty is too much territory to cover in a long weekend—but thankfully, visitors don’t have to.

The excitement has been traditionally clustered at the southern end, framed by the four towns of Lenox, Becket, Great Barrington, and West Stockbridge. But now, so-called “North County” is equally as compelling.

Pointing the compass northward affords visitors a unique look at the natural splendor and history of the Berkshires. The geographical center of this up-county area is the sigh-inducing college hamlet of Williamstown, which is flanked by a pair of little cities, Pittsfield and North Adams, each artfully reborn out of a faded industrial past.

Photo: Hotel on North

Begin your loop at the compact Pittsfield Municipal Airport—transfer there from your Tradewind flight to a well-appointed rental SUV, and in just minutes, you will have pulled up at Hotel on North, a 45-room boutique hotel that became the beating heart of Pittsfield’s downtown from the day it opened in 2015. A former menswear and sporting goods emporium, the building today is a tour de force of preservation-based remodeling, its good bones exposed and its interiors jazzed up with repurposed trim elements from the distant past. The hotel’s highly popular restaurant, Eat on North, is run by former White House chef Ron Reda.

Take the evening and part of the next day to ramble Pittsfield’s downtown and decide whether all those “Brooklyn of the Berkshires” claims are well-deserved. From District Kitchen and Bar on West Street up to Methuselah at the corner of North and Bradford to the tapas and wine bar Mission a block away, the town’s dining and drinking options invoke rustic-chic sophistication among old-city walkability. Boutiques and retro shops are in abundance, including such favorites as the décor-centric Dory and Ginger, Steven Valenti’s Clothing, and the Berkshire General Store. Morning coffee and first-rate baked goods are steps away at Dottie’s coffee shop, which also boasts the kind of meeting-place vibe that convinces people to move to resurgent communities like this.

Photo: Mission Berkshires

Route 8 out of Pittsfield takes you along the eastern edge of the 12,000-acre Mount Greylock State Reservation. It’s named for the state’s highest peak and laced with upland trails that will carry a hiker deep into the heart of a New England summer. On this trip, you may want to stop by the visitor center and pick up a trail map, in case you’re inspired to plan an outdoorsy return to the area amid October’s cooler air and bonfire-hued foliage. If you opt to skip the park and cruise directly from Pittsfield to North Adams, you’ll be there in less than 30 minutes most days.

What you’ll find on arrival is a pocket-sized city, still somewhat in recovery from a mid-1980s economic blow — but blooming back to life with plenty of charm. Today, the largest museum of contemporary art in the U.S., the Massachusetts Museum of Contemporary Art (or Mass MoCA), occupies a 24-acre campus originally built by Sprague Electric, the space-mission contractor that supplied NASA and other federal agencies with advanced circuitry and components till its closure (leading to the town’s aforementioned economic downturn).

Photo: Mass MoCA via Grace Clark

To display the works produced by contemporary art superstars like Sol LeWitt, Laurie Anderson, and Robert Rauschenberg takes vast amounts of inexpensive space — much more than the name-brand museums in big cities have available, but perfectly suited for this unlikely space in The Berkshires. Combine the need for acreage with creative vision, and you’ve got a gritty town fast on the rise whose principal industry is modern art. Odd as that may sound, Mass MoCA reportedly boosted local economic activity by $51 million in 2017 alone.

You soak up the “anything’s possible” zen of North Adams by staying at The Porches, a chic hotel on the Mass MoCA property, or perhaps at the brand-new Tourists, a self-styled “riverside retreat inspired by the classic American roadside motor lodge.” Investors from the California foodie scene designed and built Tourists and its food-and-beverage amenities, featuring a new lounge, The Airport Rooms, serving classic cocktails and a “creative roadhouse” menu. Its executive chef, Greg Thomas, was recruited from Austin, Texas.

Photo: Tourists via Peter Crosby

The artwork at Mass MoCA is vast in scale, which means you go through it more than past it, which makes the appreciation experience looser and more fun. Performing arts further increase the hip factor here — there are film screenings, rock concerts, comedy festivals, and other on-stage exuberance. The beloved and versatile band Wilco has a particular footprint at Mass MoCA, most notably thanks to its biennial Solid Sound Festival — this year, the Wilco event happens June 28th through 30th.

Also on campus is Bright Ideas Brewing, a craft brewery and taproom. Meanwhile, any left or right you take in the general vicinity of the campus will reveal some semi-pro mural or sculpture to echo the crown jewels of the museum. Admittedly, most of us lack the endurance to study art for entire mornings or afternoons — but that’s not the point here. A day in North Adams is actually akin to life inside a “60 Minutes” segment, with socioeconomic and cultural history being made in real time. (If you’re quiet, you can hear the property values rising.)

Fifteen minutes east is prim, prosperous Williamstown, where the top-ranked liberal arts college in the country (per U.S. News) seamlessly merges its verdant campus with the commercial layout of the town. In the summer, the cultural scene around Williams College is ever vibrant. This season, the Broadway-quality dramatic offerings at the Williamstown Theater Festival include one play that’s particularly easy to recommend. It’s a revival of Henrik Ibsen’s Ghosts starring Golden Globe and Academy Award nominee Uma Thurman, on stage through most of August. Meanwhile, the Clark Art Institute has a high-powered French Impressionist exhibit, titled “Renoir: The Body, the Senses,” devoted to Renoir’s unsurpassed achievement in the depiction of body figures.

Photo: Mezze Bistro & Bar via FED Guides

Dining in Williamstown won’t disappoint—perennial favorites include Mezze Bistro & Bar as well as The ‘6 House and Pub, a few minutes outside of town in a rural setting. The Water Street Grill is just right for high-quality tavern fare and live music. Tucked around the corner from Spring Street's shops, pubs, and restaurants is one of the half-dozen best public golf courses in all of New England, Taconic Golf Club. An early-20th-century classic by Stiles and Van Kleek, Taconic is owned by the college, meticulously maintained at all times and recently renovated by Gil Hanse, the most renowned course architect working today.

When your three-stop tour is over, it’s time to head south down historic Route 7 toward Pittsfield, enjoying sublime Berkshires scenery plus endless roadside attractions, from antiques to ice cream to riverfront picnic grounds. An easy hour’s ride on an old country highway, it’s ideal for reflecting on the artsy, urban fascination you’ve encountered while letting the innocence of rural New England summertime float by.

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Tradewind offers private charter flights to the Berkshires year-round on a fleet of Pilatus PC-12s. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured Photo: Tourists via Nick Simonite

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As the country’s bona fide birthplace, it’s only fitting that New England would be in a league of its own on Independence Day. Fourth of July is arguably the region’s most exciting holiday, marked by festive parades, all-American cookouts, and dazzling fireworks displays that light up the skies and reflect on the waters of the Atlantic.

From charming coastal celebrations to large-scale bashes, here’s where you can take in the best Fourth of July celebrations this summer, each accessible by Tradewind Aviation’s shuttle or charter flights.  

Nantucket, Massachusetts

Photo: Jamie Holmes

Each year, Nantucket hosts a unique July 4th celebration among its Colonial-style buildings and picturesque beachfront. The hallmark of Nantucket’s Independence Day festivities is the annual water fight between Town of Nantucket’s Fire Department and the Boynton Lane Reserves, a tradition that began back in 1981 when local real estate broker H. Flint Ranney (who had acquired a 1927 LaFrance ladder truck) challenged Nantucket’s then-fire chief Bruce Watts to a friendly battle. The event has endured, and for its 38th year, visitors can make their way to Main Street at “high noon” to cool off (the festivities officially commence two hours early at 10am).

Following the water fight, children’s games begin at 5pm, including potato-sack races, three-legged races, wheelbarrow races, and tug-of-war, followed by live music on the bandstand at 6pm. Those arriving for the weekend are in luck — this year’s fireworks show will be held on Jetties Beach on Friday, July 5th.

Recommended Airport: Nantucket Memorial Airport (ACK) via Tradewind Shuttle or Tradewind Private Charter

Martha’s Vineyard, Massachusetts
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While there are six main towns on the island of Martha’s Vineyard (each with their own distinct Fourth of July events), the community of Edgartown in particular stands out for its time-honored traditions. The day centers around a late-afternoon parade at 5pm, where onlookers watch as elaborate floats, antique cars, marching bands, and more travel down Main Street and its surroundings. For prime viewing opportunities, arrive early to claim a spot in the historic town center, known for its white Greek Revival-style architecture (which, ironically, feels quintessentially New England).

The festivities continue on the harbor with a fireworks show at dusk, best viewed from Memorial Wharf. Past years have also included the Martha’s Vineyard Preservation Trust’s annual barbecue on the lawn of the Dr. Daniel Fisher house on Main Street, featuring cookout classics from burgers to hot dogs. St. Elizabeth’s Church has been known for their lobster rolls during the afternoon, and live music has been held at Old Whaling Church.

Recommended Airports: Martha's Vineyard Airport (MVY) via Tradewind Shuttle or Private Charter; Katama Airpark (1B2) via Tradewind Private Charter 

Bar Harbor, Maine

Photo: BHCOC

An old-fashioned Fourth of July celebration can be found on Mount Desert Island in the town of Bar Harbor. Just off of Maine’s Down East shoreline, their festivities are regularly voted among the top Independence Day events in the country, and it’s not hard to see why, given the town’s seemingly endless things to do on the holiday.

The day commences with a blueberry pancake breakfast from 6am to 10am. Or, for a more athletic kick-off, runners can sign up for a 100-kilometer relay in teams of two to nine participants, with start times beginning at 6am. The race route offers a scenic overview of the rocky Maine seaside against the lush backdrop of Acadia National Park, along with every town and village on the island.  

Make sure to be back in time for the community parade through downtown Bar Harbor at 10am and the seafood festival at 11am, where fresh lobster, mussels, corn, and more are paired with an outdoor concert and followed by the annual lobster races (betting on your favorite crustacean is encouraged, as proceeds go toward the MDI YMCA Scholarship Program). The day also includes a nonprofit showcase, a craft fair and marketplace, and plenty of live music throughout the town, from Agamont Park to Bar Harbor Village Green. The festivities conclude with breathtaking fireworks over Frenchman Bay at 9:15pm.

Recommended Airport: Hancock County Bar Harbor Aiport (BHB) via Tradewind Private Charter

Bristol, Rhode Island
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Known as “America’s most patriotic town,” Bristol, Rhode Island boasts the world’s first Fourth of July celebration, and its revelry has only grown in the 234 years that have passed. In true over-the-top fashion, the town doesn’t wait for July 4th to begin celebrating —  activities and events officially commence on June 14th with a Flag Day Ceremony. In the weeks that follow, local organizations hold events including a free concert series at Independence Park, the Bristol Stomp Block Dance on June 15th, the annual Fourth of July Ball on June 21st, the Bristol Independence Rhode Race Half Marathon on June 29th, and even a Patriotic Pet Photo Contest from June 17th -30th.

Rather than mark the end of the holiday, the town’s fireworks show is held on June 3rd at 9:30pm on Bristol Harbor, building excitement for Independence Day itself. The next morning, the town wakes to the churches’ Ringing of the Bells at 6am, followed by the Military, Civic, and Firemen’s parade at 10:30am, viewed by more than 200,000 onlookers. Blending small-town charm with grand spectacle, it’s an unforgettable gathering for both locals and visitors.

Recommended Airport: Newport State Airport (UUU) via Tradewind Private Charter 

Boston, Massachusetts

Photo: Michael Blanchard

Boston is steeped in colonial history year-round, but its revolutionary beginnings are fully celebrated on the Fourth of July. The mayor starts with a speech at City Hall Plaza at 9am, and from there, a festive parade makes its way toward the Old State House, where a stirring reading of the Declaration of Independence takes place on the balcony. Recited by the Captain Commanding of the Ancient and Honorable Artillery Company of Massachusetts, it’s a meaningful annual tradition for the city of Boston as a reminder of the nation’s roots.

Before this tradition takes place, the parade stops at the Granary Burying Ground on Tremont Street for a fitting tribute to the founding fathers. Here, officials lay wreaths on the patriots’ graves, including John Hancock, Samuel Adams, and Robert Treat Paine.

The day’s entertainment culminates with the renowned Boston Pops Fireworks Spectacular. This free (and televised) orchestra concert at the Hatch Memorial Shell on the Charles River Esplanade begins at 8pm (though gates open at 9am for those dedicated to getting a seat). Led by famed Boston Pops conductor Keith Lockhart, this year’s event will also feature Queen Latifah, Arlo Guthrie, and more. The fireworks lend a dramatic, awe-inspiring touch at 10:30pm, closing out the evening with a bang.

Recommended Airport: Boston Logan International Airport (BOS) via Tradewind Private Charter

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The ocean’s most feared apex predators, great white sharks, have triumphantly returned to Cape Cod and its surrounding islands. But there’s no need to cue the Jaws theme: While their return may not sound like good news to beachgoers in the Northeast, the sharks’ reestablished presence provides visitors a unique opportunity to experience these misunderstood, majestic creatures in an authentic and safe way.

The Atlantic White Shark Conservancy (AWSC) offers a number of ecotours designed to give the public a better understanding of the great white comeback (spurred by a rebound in the grey seal population), allowing them to see firsthand what scientists are doing to help man and shark peacefully coexist. AWSC’s most thrilling adventure? Its “Great White Shark Expedition,” a once-in-a-lifetime chance to get up close and personal with the Cape’s most notorious resident (and live to tell the tale).

No, this isn’t a controversial cage-diving experience like those common in South Africa, where waters are chummed and seal dummies are thrashed around to attract and excite the sharks. This is a research-based wildlife interaction in which participants shadow shark researchers as they tag, identify, and study great whites off the coast of Cape Cod.

In partnership with Chatham Bars Inn, AWSC runs the expeditions twice daily on Wednesdays, Thursdays, and Sundays from July 3rd to October 27th (weather permitting). Departing from the pier at Chatham Bars Inn and accompanied by a member of AWSC's team, a maximum of five guests head out into prime great white real estate. Sharks are detected using aerial surveys from the research team’s Cessna plane overhead, through shark receivers, and with AWSC’s Sharktivity app, which monitors the whereabouts and activity of previously tagged great white sharks in the area.

Once spotted, sharks are slowly approached, and a hydrophone is placed into the water to determine if the shark has already been tagged. If so, the shark’s coordinates are matched to the app. If not, scientists may attempt to tag the great white. In all cases, the sharks are identified — the team is on a first-name basis with most sharks, seeing them daily and already knowing each one’s personality traits. Observations are then logged by the team.

There are many purposes for this trip: First, you’ll witness conservation in action as scientists collect data used in behavioral and ecological studies of great whites. Next, you’ll get to participate first-hand in mitigating human-wildlife conflicts (the Sharktivity app uses the information gathered to send alerts to researchers and the public when tagged sharks get a little too close to the shoreline for comfort). Moreover, you’ll become an ambassador for helping debunk the myth of great whites as man-hungry villains. In fact, you’ll be stunned at how shy many of the great whites appear upon approach and how they go about their daily business along the Cape, rarely bothering beachgoers. (In fact, the latest shark attack stats from 2018 indicate a slim 1 in 3.75 million chance of being attacked.)

Of course, as this is nature, shark sightings are never guaranteed. That said, on Goodspeed’s particular Great White Shark Expedition, five were spotted at close range. If this experience sounds a little too intense, AWSC also offers one-hour “Receiver Excursions” on Mondays and Wednesdays from July 1st through September 2nd, 2019. On this trip, you’ll cruise around the seal-rich Chatham Harbor with AWSC staff, looking for signs of predation and analyzing data from a shark receiver and Sharktivity.

Another AWSC adventure to consider is the all-day “White Sharks and Whales” group expedition, where guests will seek out great whites plus humpback whales and seabirds. Taking place only twice per year, the trip leaves from Plymouth, Massachusetts and includes breakfast, lunch, and a souvenir T-Shirt. Dates this year are September 7th and Sept 14th, 2019. 

Whichever excursion sounds most exciting, visitors to Cape Cod shouldn’t miss out on their chance to play a role in the area’s great white shark comeback story.

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Tradewind Aviation offers charter flights to Cape Cod year-round. Great White Shark Expeditions are $2,500 per boat for up to five passengers (most of this fee goes directly to research and is tax deductible). Receiver Excursions are $55 per person; White Sharks and Whales trips are $160 per person. To learn more and book your shark expedition, call AWSC at 1-800-527-4884. 

All photos courtesy of AWSC.

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In the northeast corner of New England, Maine’s Down East shoreline is a rugged stretch of snaking inlets and lighthouse-studded peninsulas. (In fact, unfurled into a straight line, the state’s Atlantic border would total more miles than the entire California coast.) This vast seaside was carved out by a long-gone glacier, which also left a legacy of sprawling bays strewn with forest-covered islands.  

Among them is Mount Desert Island, the Down East’s crown jewel and home to its charming gateway town of Bar Harbor. Singular in its brand of natural beauty, this Northeast enclave is a stunning haven of mountain forests, colossal granite cliffs, and rocky coastline.

Fitting, then, that the island also features Acadia National Park, America’s first designated wilderness area east of the Mississippi — and its most visited today. It’s not hard to see the allure: The national park and its town are a sanctuary for over 40 species of native wildlife, and the island is laced with 125 miles of hike-able trails.

With at least 25 distinct hikes spanning every level of difficulty to choose from, here are five Mount Desert Island favorites. Make your way there on a Tradewind charter flight to Bar Harbor, and from there, the trailheads wait just a short distance from the town.

The Ocean Path

Photo: Christian Collins via Flickr / CC BY

For a leisurely stroll that’s filled with natural wonders, try the Ocean Path, which meanders along the coast for two miles between Sand Beach and Otter Point. With its flat, obstacle-free terrain, this paved path is one of the most family-friendly trails on the island.

No matter which direction you decide to take (the path is accessible from terminal parking lots on both the Beach and Point sides), this walk provides a captivating yet peaceful glimpse of coastal Bar Harbor. It’s beautiful in every weather condition, too — which is good news, considering it swaps daily (if not hourly) between sunshine and atmospheric fog.

Halfway through the walk is Thunder Hole, a unique fissure in the craggy rocks where the crashing waves transform into roaring geysers up to 40 feet high. Between this awe-inspiring spectacle and the tide pools of Otter Point, you’ll also find the bumpy cove of Boulder Beach, named for its collection of bowling ball-like rocks that have been smoothed out by the tumultuous Atlantic. Built up over centuries on the east-facing shore, they glow like a field of pink gumdrops with the rising sun.

Gorham Mountain Trail

Photo: NPS/Victoria Stauffenberg via Wikimedia Commons / CC BY

Close to the Ocean Path (just past Thunder Hole) is the entrance to Gorham Mountain Trail, a moderate hike that’s 525-foot summit offers scenic overlooks of the topography below and the adjacent peaks. As an added bonus during the summer, this jaunt is lined with vibrant Wild Maine blueberry bushes (so it’s no surprise that hikers can often be seen descending with purple-stained fingers).

Follow the route from the trailhead as it slopes gently up the side of the mountain through a spruce forest. When the trail forks, either way will get you to the top (they rejoin further ahead), but those looking for an easier path should veer left, where there are fewer natural hurdles.

Eventually, the woods will empty out into a beautiful clearing that’s often mistaken for the peak. Take some time here to soak in the views of the Otter Cliffs and Cranberry Islands before continuing to the true summit just ahead, complete with its own spectacular eagle-eye vantage of both land and sea.

Cadillac Mountain

Rising 1,528 feet above sea level, Cadillac Mountain is not only the tallest of Mount Desert Island’s 20 peaks; its summit is also the highest point along the North Atlantic seaboard. From October to March, the mountaintop is known as the first place in the United States to spot the rising sun.

There are multiple ways to reach Cadillac’s precipice and its panoramic views, and they vary in difficulty. Via the paved Cadillac Mountain Road, those with limited time or mobility can actually park at a lot near the top before walking its scenic, 0.3-mile loop. Alternatively, Cadillac’s winding road (which inclines gradually over 3.5 miles) can be easily navigated from the bottom.     

For less pavement and more trail, take the out-and-back North Ridge Trail, a moderately difficult but visually magnificent open ascent. To find the trailhead, park in the ME 233 lot (located a few miles west of Bar Harbor), head down Park Loop Road until you find Kebo Brook Trail, and follow it for less than half a mile. There, you’ll find the beginning of North Ridge Trail, making way for three picturesque miles to Cadillac’s pinnacle.    

A more strenuous path is the South Ridge Trail Loop. Toward the summit, the forested trail opens up to a granite face, and some boulder scrambling is required to conquer the steep slope. However, hikers are immediately rewarded with expansive views of the national park and the Atlantic, as well as the nearby Porcupine Islands perched in the foreground of Frenchman’s Bay, their hills bristling with pines.

Jordan Pond Path

Photo: Naya Sriramaneni via Wikimedia Commons / CC BY

Tracing a 3.3-mile circuit around Acadia’s deepest (and second largest) lake is Jordan Pond Path. Though most of the loop is easy to navigate (transitioning between patchworks of flat ground and wood-plank walkways), this hike’s moderate difficulty comes as the path crawls across some uneven granite on the pond’s northwest side.

Hugging the shoreline, the trail teems with aquatic wildlife, including frogs, beavers, birds, and more. The path also offers plenty of stopping points to savor the surrounding mountains, which frame the placid pond from nearly every angle.

Take some extra time to look across the lake from its southern edge, which on clear days features the domed peaks of South and North Bubble Mountains rising over the water and reflecting on its glassy surface. To satisfy post-hike hunger, the south side of the lake is also home to Jordan Pond House, the national park’s only full-service restaurant, which has held wild acclaim for its popovers (served with butter and Maine strawberry jam) for at least the past 125 years.

Bubble Rock 

Photo: Heidi via Wikimedia Commons / CC BY

While each of the twin Bubble Mountains on Jordan Pond’s north side has a unique pathway to its respective summit, the south peak is popular due to a peculiar landmark left behind long ago by a glacial retreat: Bubble Rock itself. Permanently perched on the side of a cliff, it’s seemingly on the brink of tumbling into the wilderness below.

To see the boulder up close, park in the Bubbles parking lot before taking the Bubbles Divide Trailhead west through the forest, where it cuts through the valley separating the north and south peaks. Soon after passing the North Bubble trail on the right side, the South Bubble trail will emerge on the left. Follow this easy path until it ascends to the summit, and look for the small side trail leading to Bubble Rock, plus breathtaking views of Jordan Pond from above.

When it’s time to head back down, those with children will want to backtrack using the same easy route. Others looking for a more adventurous descent can continue down the South Bubble Trail, which requires some clambering as it weaves in switchbacks down the cliffside, eventually joining up with Jordan Pond Path. 

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Tradewind offers private charter flights to Bar Harbor year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured Photo: Christian Collins via Flickr / CC BY

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A Tradewind flight across Long Island Sound to Fishers Island offers plenty of breathtaking East Coast views. But for golf aficionados soaring over the eastern end of the seahorse-shaped island, none are more spectacular than the golf perfection spread out below.

Just off the coast of Connecticut, Fishers Island Club opened in 1926 during what’s considered the golden age of course-building. One of the era’s most brilliant architects, Seth Raynor, designed a dozen-plus courses during this time that are still celebrated today — but you’d be justified to call this one his masterpiece. 

Among the experts echoing this view is Thomas Dunne, director of the Golfweek magazine course-rating panel and co-founder of literary golf journal McKellar. He considers Fishers Island to be “one of the 10 best properties for golf anywhere on Earth.”

There’s a section of the course, beginning with the par-4 4th hole, that Dunne finds particularly inspiring. “To me, it’s the greatest nine-hole run in the world,” he says, “if you combine the natural environment with the excellence of its design and construction.”

Gil Hanse, arguably the most sought-after course architect in the world these days, has played Fishers Island many times and finds it unsurpassed as a combination of stunning visuals and strategic subtlety.

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“The first time you play it, you can’t appreciate it architecturally,” says Hanse, who designed the course for the 2016 Olympics in Rio de Janeiro. “There’s too much beauty to take in, too many water views — [the] Atlantic Ocean, Fishers Island Sound, [and] tidal marsh all frame what you see and tend to mask the complexity of the design.”

He’s talking in part about angles of play — the geometry at work as targets are chosen and a player balances risk-reward. “The third hole, a par-4, has an elevated fairway and a green very exposed to the wind,” Hanse says. “If one golfer opted to drive down the right side and his partner hit a drive down the left, they’d basically be playing two different golf holes — and you’ll find strategic variation like that throughout the round.”

You can’t write about a Seth Raynor course without mentioning the design “standards” or “template holes” he so loved. These have intriguing names like Redan, Eden, Punchbowl, Alps, Biarritz, Double Plateau, and Cape. Along with his mentor, Charles Blair Macdonald, Raynor made a habit of including architectural elements that pay homage to beloved golf holes on historic British courses.

Fishers Island embodies that philosophy in fine fashion. It’s even got an Alps-Punchbowl combination — dramatically high mounds guarding a large, bowl-shaped green that will mercifully kick an off-target shot back toward the flagstick.

Considering his legacy, it’s no surprise that there’s even a Seth Raynor Society. It’s administered by Anthony Pioppi, a writer and course expert who recently published the book The Finest Nines: The Best Nine-Hole Golf Courses in North America.

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In the name of participatory journalism, Pioppi made the mid-life decision to caddie on Fishers Island for several summers, during which he absorbed the quirks and cadences of life “seven miles from reality,” as he and others have described the island.

“People there are genuinely friendly, and part of that is because everyone crosses paths everywhere,” says Pioppi. “There are two bars — if you count the American Legion bar — and one grocery store. At the checkout counter you’ll see a club member, a waiter, and a grounds crewman in line together, all making casual conversation.”

The need for caddies is based on the course’s extreme walkability. After finishing a hole, you stroll directly to the next tee, steps away. The flow of the round is never interrupted, except by the beckoning views. Pioppi, as a caddie, would encourage first-time players to “put their scorecards away and just settle into the experience.” At the completion of a hole, he might keep his foursome at the green and have them try chips and putts from various locations to fully appreciate the course’s design subtleties and unique challenges.

Part of what’s magical about flying to Fishers is the 36-hole factor. Not that someone arriving and leaving by ferry couldn’t go around twice in one day, but it’s much easier to make that happen when you’ve got air travel going for you. One Connecticut PGA professional, so thankful for his invitations to play the course that he asked to speak anonymously, has a plane-owning, golf-loving friend with whom he’s made the hop to Fishers more than once.

“We go wheels-up around 7 a.m., get on the tee by 8:15, play the course twice and we’re back home for dinner,” he says. “Meanwhile, you feel like you’ve gone back in time when you’re there. Nothing ever changes. There’s tremendous wealth, but the property owners consider the island just perfect the way it is.”

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Lest you’re concerned that Fishers Island Club is a golf mecca you’re not destined to visit, there are several charity tournaments open to off-island golfers who wish to support a good cause (while checking off a major bucket-list item). In the springtime there’s a fundraiser outing for the Eugene O’Neill Theater Center in Groton, Connecticut, which is across the Sound from Fishers. Also in the spring, the club hosts an event to benefit Fishers Island churches. This year on September 16, it’s the Next Step Fishers Island Charity Golf Tournament, supporting skill development of young people with serious illnesses. Scouting online, you’ll find rounds of golf at the club included in silent auctions by one charity or another.

Of course, if you do happen to have a friend who’s a member, you’ll be playing for your own good cause: Sublime enjoyment of oceanside golf at its absolute finest.

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Tradewind offers private charter flights to Fishers Island year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

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When it comes to brews, Martha’s Vineyard hasn’t historically been a craft beer hotspot — but thanks to breweries like Bad Martha and Offshore Ale Company, the island is catching up in stride.

Situated off the south coast of Cape Cod within Tradewind’s regular charter and shuttle routes, Martha’s Vineyard has maintained a hyperlocal focus throughout its recently burgeoning brewery scene. Apart from hiring local residents and using ingredients from across the island, the beer purveyors of Martha’s Vineyard have given back to their tight-knit community in myriad ways from the beginning.

In downtown Oak Bluffs, the island’s neighborly atmosphere is evident at Offshore Ale Company, the Vineyard’s first brewery (opened in 1997). Family-owned and operated, it’s a lively, nautically-themed establishment that residents love to frequent for its complimentary peanuts, brewpub-style seafood, live music, and, of course, its award-winning pints (many of which are named after Martha’s Vineyard icons and landmarks).

The brewery has also long dedicated itself to giving back to the community by donating a portion of its proceeds to various local organizations. Since 2009, Offshore’s “Pints for a Purpose” program has given a percentage of its sales from their East Chop Lighthouse and Menemsha Creek pale ales to benefit the Coast Guard Foundation, and profits from their West Coast-style Lazy Frog IPA aid in financing the island’s disc golf course.

Likewise, their popular late-summer Blue Lobster Belgian Strong Ale supports funding for the independently-operated MVY Radio, and their annual Dine-To-Donate events help a rotating roster of charitable groups (this year’s recipient was Martha’s Vineyard Playhouse, a theater-focused nonprofit).   

On the northeast side of the island, just five miles south of Offshore Ale Company, patrons of Bad Martha are encouraged to live on the wild side as they kick back with one of the brewery’s small-batch libations. But contrary to their name, doing good is one of Bad Martha’s core values. Since establishing the Edgartown mainstay in 2014, owner Jonathan Blum has left his corporate background behind on the mainland in favor of the Vineyard’s longstanding tradition in fostering intimate island connections.

Churning out over 40 unique barley pops in any given year, Bad Martha sources their signature flavors almost exclusively from the island’s bountiful harvests, while simultaneously supporting local family-owned ventures.

“Since the beginning, we’ve tried to use as many local ingredients as possible, and that’s pretty much whatever we’ve been able to get our hands on, from blueberry to cherries to beach plums to honey,” says Bad Martha operations manager Josh Flanders. “Speaking of honey,” he adds, “there’s Honey Helles lager, one of our fan favorites that sells out in the summer about a week after we brew it. With the number of honey and bee farms on the island, we take as much as we can from them.”

Other popular beers include a stout crafted with chocolate from Not Your Sugar Mamas confectionary shop, a coffee porter made with beans from Chilmark Coffee Company, and a refreshing jalapeno and cucumber lager sourced from the 65 acres of nearby Morning Glory Farm. “We’ve taken to calling that one Shark Bite,” Flanders says. “That’s a unique beer people get really excited for. They ask for it all year long.”

Regardless of the season and its corresponding batch, Bad Martha recycles their spent grain byproduct from each brew by giving it to local farmers for livestock feed. “We’re directly tying our brewing to not only the ingredients we’re getting in, but also giving those ingredients back out,” Flanders explains. “There’s plenty of nutrition left in the grain after that early brewing process, so it’s really a win-win for having a way to get rid of it and helping farmers save some cost in feeding their animals, and making those pigs and cows happy.”  

The brewery’s philanthropic gestures are appreciated by plenty of humans, too, from Puerto Rico relief efforts after Hurricane Maria to fundraisers closer to home, like the annual Fluke for Luke tournament (a memorial fishing event honoring a local who passed away in a boat accident in 2016). “We’ll donate beer here and there, or anything else we can offer. Usually it’s beer, because that’s what we’ve got,” Flanders laughs, adding that if an organization wants to use the taproom space for fundraising events, the brewery offers it free of charge.

But Bad Martha’s biggest contribution comes toward the end of every year, when they give a bulk percentage of their annual profits to Island Food Pantry, a Vineyard nonprofit helping residents in need by providing basic nutrition. Around last Christmas, they were able to present a $7,500 check to the charity during a time of year when such resources are most needed.     

“Craft beer is a luxury item,” Flanders says. “We’re happy to provide it but there are people out there who aren’t thinking about drinking craft beer, but about how to feed themselves and their family. We can’t improve their lives just by being a business, so I think it’s important for us to give back to those people as well, the people who are really in need in the community.”

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Tradewind offers regularly scheduled shuttles to Martha’s Vineyard from May through November (with up to 15 flights per day Thursday through Monday), as well as private charters year-round.

All photos courtesy of Bad Martha.

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As winter thaws and warmer weather approaches, the countdown has begun for two of New England’s most celebrated food and wine festivals of the 2019 season: the Nantucket Wine & Food Festival (May 15-19) and the Newport Oyster Festival (May 17-19).

For its 23rd anniversary, the Nantucket Wine & Food Festival will host more than 60 exciting events, from socialite-studded tastings and lavish dinners to informative wine seminars. Meanwhile, in its fourth year, the Newport Oyster Festival on Bowen’s Wharf kicks off with an intimate Friday night opening party before moving into two full days dedicated to all things oysters, set to spirited live music.

Here, the scoop on two epicurean spring flings you’ll find in the Northeast this year, each located in charming coastal destinations accessible by Tradewind Aviation.

Nantucket Wine & Food Festival

May 15-19, 2019

Photo: Nantucket Food & Wine Festival

This wildly popular five-day Nantucket festival marks the official start of season, celebrating the Grey Lady’s return to New England’s social and culinary scenes.

Since its humble beginnings as a small-scale, single-day celebration in 1997, the Nantucket Wine & Food Festival has blossomed into one of New England’s most anticipated annual events. Today, it’s where the best-of-the-best regional chefs unite with more than 150 esteemed wineries — from as far as New Zealand to as close as Long Island — and host grand dinners, wine and food seminars, grand tasting events, luncheon symposia, and more.

Book early for seats in the “Great Wines in Grand Houses” series, featuring venerable chefs working with coveted wineries to deliver one-of-a-kind paired menus in private island homes. For example, on May 18, award-winning chef and restaurateur Michael Scelfo (of Alden & Harlow fame) teams up with third-generation Italian winemaker Federico Ceretto at a local mansion for a four-hour journey through Ceretto’s namesake varietals, with sublime cuisine to match ($700).

Photo: Nantucket Food & Wine Festival

The festival hits its peak during the two-hour “Grand Tasting” sessions at the White Elephant hotel (two on May 18, starting at $185 and one on May 19, $135). These three sessions are the main events: Festival-goers have the opportunity to sample 600+ wines from 150+ global wineries, all while enjoying bites from local restaurants and mingling with fellow oenophiles.  

Those looking to pepper established festival favorites with out-of-the-box experiences have plenty of options, too. For example, consider “Sake + Sashimi,” a tasting hosted by sake expert Rachelle Bose and complemented by sashimi pairings from PABU Boston ($125).  Or, rise and shine for “Namaste then Rosé,” a morning of vinyasa yoga paired with a cooking demonstration and some heavy pours of the good stuff with winemaker Susana Balbo and celebrity chef Elizabeth Falkner. An intoxicating combo of wellness and wine? We’ll toast to that.

www.nantucketwinefestival.com

Newport Oyster Festival

May 17-19, 2019

Photo: Trixie Wadson, Bowen’s Wharf Co.

This foodie-fueled festival is an immersion into Rhode Island’s ocean-to-table and locavore movements. For one weekend, the state’s oyster farmers gather at Newport’s Bowen Wharf to showcase their fresh catches to the public and offer insight into the state’s thriving aquaculture industry.

The weekend begins with an intimate opening party (limited to 200 participants, $125) benefiting the Ocean State Aquaculture Association, The Nature Conservancy, and SSV Oliver Hazard Perry (Rhode Island’s official Sailing School Vessel). Under the festival tents, guests feast on unlimited freshly shucked oysters from eight leading farms while sipping Champagne from an open bar. The event also offers the chance to spend time with regional farmers and local business owners, with noted Rhode Island folk music group Atwater-Donnelly in the background.

From 11am to 5pm on Saturday and Sunday, the wharf buzzes with festival-goers eating and imbibing to the beats of more live music. Sets from six bands represent different genres, ranging from rock and funk to reggae and jazz. Visitors can sample fruits of the sea from 13 different oyster farms — advance purchase tickets include six fresh RI oysters and a beverage for $27. Attendees can also expect a sugar rush from the “Sweets Tent” and learn about aquaculture and reef restoration from The Nature Conservancy educators. 

www.bowenswharf.com

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Tradewind Aviation operates daily shuttle flights to Nantucket from late April through early December, as well as private charter flights to Nantucket and Newport year-round.

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30 miles off the coast of Cape Cod, a New England enclave is gearing up for spring.

Every year during the last week in April, Nantucket hosts a colorful fête to celebrate the approaching season and symbolize the island's reawakening after a long Northeast winter. True to its name, the Daffodil Festival — or “Daffy Day,” as it’s affectionately dubbed by locals — is synchronized to millions of yellow flowers unfurling from their slumbers in the thawing ground.

“Daffodils are hardy, they’re dependable, and they’re resilient, so I think all those things are very representative of the natives of Nantucket,” says Maddie Hjulstrom, an island resident and member of the Nantucket Chamber who helps organize the event. “It’s quite cold and quiet in winter, but to see those yellow blossoms poke through the soil every year on schedule is very much like the residents who stick it out and manage to live there year-round.” 

Photo: William DeSousa-Mauk

The annual tradition started in 1974 when Jean MacAusland, a Nantucket resident and former publisher of Gourmet magazine, had the idea to amplify the island’s springtime beauty. Apart from organizing an annual flower show sponsored by the American Daffodil Society, MacAusland enlisted the help of landscapers and friends to plant one million daffodil bulbs throughout the island.   

As Hjulstrom explains, daffodils are the perfect flower to thrive on Nantucket because they are one of the few unappetizing plants to the island’s flourishing deer population. And because the flowers are self-propagating (meaning they reproduce on their own), springtime now bears witness to millions of vibrant blossoms emerging like clockwork across the landscape each April and May.  

Now preparing for its 45th consecutive run, the Daffodil Festival incorporates an annual flower show at Bartlett’s Ocean View Farm (including daffodil displays from all over the country), as well as an array of other spirited festivities held throughout the long weekend. And for non-residents wishing to experience the springtime essence of Nantucket, the island waits just a Tradewind flight away from the New England coast.

“The whole thing kind of blossomed into what can we do in the spring to get people excited about being on Nantucket and to celebrate the season,” Hjulstrom says. “All in all, it’s a wonderful way to welcome the milder weather back to the island.”

Photo: Tim Ehrenberg (left: with husband, James; right: with best-selling author Elin Hilderbrand)

The lively tradition has certainly made an impact on residents like Tim Ehrenberg, who moved to the island with his husband in 2013 and now owns Brand New - Nantucket, a marketing consultancy for local businesses and non-profits. As a newcomer to Nantucket, Ehrenberg hadn’t heard of the Daffodil Festival until someone asked him if he had his outfit ready the week before.

“And since then I seem to buy a new outfit every year,” explains Ehrenberg, who now starts planning for the special day as far back as March to sport everything from bright green pants to full floral suits. “I have more floral pants than anyone should own.”

Adding to the spectacle of costumed locals is the antique car parade that crawls down the cobblestoned Main Street. Held on the Saturday of each festival, the tradition showcases up to 120 classic vehicles decked out in the lemon-hued blossoms, all in eager competition for the “Best in Show” trophy. When cars finish the downtown parade, most of them converge on the eastern end of the island to a town called ‘Sconset before parking for individually themed tailgate picnics, which are judged on their elaborateness and creativity.     

“People sometimes go to extraordinary extents for a truly memorable picnic experience,” says Hjulstrom, who remembers one theme with picnickers dressed as super heroes, and another featuring a jeep packed with green-painted soldiers posing as plastic toy army men. “People have a lot of fun with it.”

Photo: William DeSousa-Mauk

Back in downtown Nantucket, the weekend celebration continues with a rolling roster of events including a Daffy Hat competition and dog parade, where residents bring their florally costumed canines for a festive procession and contest benefitting the Nantucket Island Safe Harbor for Animals. Here, as local shops reopen their doors for the impending high-season, almost every window is adorned with flashy flower motifs.

The weekend lineup also features several daytime tours and nightly ghost walks for visitors to stroll around Nantucket and savor tales from its storied past dating back to 1641. And just a short walk from downtown, on Children’s Beach, festival organizers have begun to host a variety of family-style events such as the Children’s Bicycle Parade, where youngsters decorate their bikes with daffodils before pedaling through a designated course near the surf. 

“[The weekend] evokes so much more than just daffodils," Ehrenberg says. "It's the beginning of the season for us locals and all of the anticipation [of the summer] to come, from festivals to beach days, and from drives to Great Point to sunsets at Jetties to Sunday brunches at CRU.”

Photo: Jamie Holmes

As Nantucket’s spirit comes alive with the festival each spring, it reanimates to a backdrop of umpteen daffodils, either sprouting from its verdant landscape or plucked and placed in artful fashion.

While the original one million bulbs (and their offspring) can be seen year after year in full force, additional bulbs are also put in the ground each season by Palliative & Supportive Care of Nantucket. The specialized healthcare non-profit appoints students from the New School on Nantucket to symbolically plant flowers every year in honor of people who have passed on.

The annual festival is meaningful in many ways to the island, its visitors, and its residents. “Nantucket locals in winter tend to hibernate, not really leaving work or home, but on Daffy Day, everything and everyone seems to wake up,” Ehrenberg says. “There are flowers in the window boxes, businesses are open and most everyone is smiling, laughing, and saying 'Happy Daffy' as you walk by them. It's a community event that I absolutely adore.”

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Tradewind Aviation operates daily shuttle flights to Nantucket from late April through early December, as well as private charter flights year-round.

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While there’s no shortage of adventure to be found on a Caribbean vacation, sometimes, the best activity is none at all. Kick back with a tropical cocktail at one of these six incredible Caribbean beach bars, where you can admire the ocean blues, enjoy refreshing island fare, and maybe even plant your feet in the sand. If wanderlust strikes, a Caribbean escape is only a Tradewind flight away.

Cip by Cipriani’s, Anguilla

Photo: Cipriani Anguilla

Anguilla resort Cap Juluca reopened in December 2018 as a new flagship Belmond property, and its reincarnation brought in a slew of incredible beachfront bars and restaurants. Our favorite: Cip by Cipriani’s, an offshoot of the Belmond Hotel Cipriani’s culinary hotspot in Venice. Grab a front row seat by the impossibly beautiful Maundays Bay, order a bottle of rosé and some classic Italian bites, and let the hours slip by. 

Eden Rock Beach Bar, St. Barths

Photo: Laurent Benoit

Eden Rock St Barths may not reopen until late 2019, but its fabulous new beach bar is already up and running — and buzzing. St. Barths’ legendary people watching, celebrity spying, and fashion spotting comes to life across St. Jean Bay, with a cold glass of fine French wine in hand. Enjoy the views on a high-top stool at the bar, or get cozy on a beach lounger.

Plage, St. Barths

Photo: Plage via Le Sereno

In rebuilding Le Sereno St. Barth after Hurricane Irma, the property added a new toes-in-the-sand beachfront restaurant, Plage. With prime views of Grand Cul de Sac bay, it has the kind of vibe that makes you want to stay a while. As the palm trees sway above, sip on a Sereno Spritz (June liqueur, freshly muddled raspberry, grapefruit juice, peach bitters, and prosecco), nibble on the red Sicilian prawn carpaccio, and take in every moment of the good life.

Sandy Island, Anguilla

Photo: Paul Rubio

When Hurricane Irma struck in 2017, she swallowed much of Sandy Island, which was home to an eponymous beach shack. But Sandy Island has resurfaced with a dreamy 360-degree beach, a rebuilt restaurant pavilion, and plenty of umbrella-capped beach beds for those languid beach days. Order the “Crazy for Crayfish” — it’s the Anguillan delicacy in its best BBQ form — and wash it down with the secret-recipe JoJo Rum Punch. You can access this slice of paradise by private boat or the island’s daily water shuttle, which leaves from Sandy Ground Beach on the Anguilla mainland. Oh, and prepare for a wet landing (it’s part of the experience). 

Soggy Dollar, Jost Van Dyke, BVIs

Photo: Soggy Dollar Bar

No beach-bar hopping experience across the British Virgin Islands is complete without a stop at Soggy Dollar, a Jost Van Dyke icon. After all, this is where the “Painkiller” cocktail was born and perfected in the 1970s. Following a 2018 rebuild, it’s once again possible to enjoy this heady mix of premium dark rum, cream of coconut, pineapple, and orange juice (topped with fresh-grated Grenadian nutmeg) with local yachters.

Sunshine’s Beach Bar & Grill, Nevis

Photo: Four Seasons Resort Nevis

Though it’s situated right next to the gorgeous Four Seasons Resort Nevis, there’s nothing glamorous about Sunshine’s Beach Bar — and that’s exactly its charm. The brightly colored bar is low on frills and packed with local barflies, and it pumps out reggae music day and night while serving super-strong drinks that’ll knock you off your feet. For the true Sunshine’s experience, order the “Killer Bee” rum punch, which goes down way too easy and, as the name suggests, stings in the end. Sunshine’s is the kind of under-the-radar bar you’ll reminisce about long after your Caribbean vacation (at least, what you can recall).

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Tradewind Aviation offers regularly scheduled service to St. Barths, Anguilla, and Nevis and charter service to the British Virgin Islands.

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For today’s sophisticated businessperson, accessible air travel is a must. What many don’t realize, however, is that an enticing alternative to private jet transfer exists in the form of smaller turboprop planes, like Tradewind Aviation’s Pilatus PC-12.

Since debuting in the airline market in 1991, the Swiss-made Pilatus PC-12 has gained a reputation for its reliability, performance, and versatility, combining the speed and air-pressurization of a King Air with the cabin space and short-field performance of a Grand Caravan. As travelers discover that the smaller aircraft is just as safe as larger planes (and often comes with a lower price tag), more and more are turning to turboprop charters as a part of their productive business strategy.

“The Pilatus PC-12 offers the comfort and convenience of a private jet for significantly less cost, making it a smart business tool for short- and medium-range trips,” says Tradewind Vice President and Co-Owner David Zipkin. He also adds that the turboprop is ideal for stage lengths of up to 350 miles, such as Teterboro to Boston, Westchester to Toronto, Teterboro to Syracuse, or Westchester to Pittsburgh.

For instance, travelers flying Tradewind’s charter option from Westchester Airport to Boston Logan International and back can expect to pay around $4,700 per day trip. Compare that to using commercial business class, where a similar journey from LaGuardia to Boston and back for eight people costs around $5,200—or to private jet travel—which can run upwards of $10,000 roundtrip.

While Zipkin says that customers are often surprised by the lower costs they experience when choosing charter, they tend to be equally amazed by the amount of time they can save compared to commercial airlines, especially on shorter trips.

Whereas jets are often subject to re-routing due to their higher airspeeds, he explains, turboprops are often able to fly more direct paths, resulting in the same or shorter travel times. Considering the ability to bypass TSA and arrive at the valet-ready tarmac just 10 minutes before a scheduled departure, customers can expect to shave off up to five hours per round trip.

Zipkin adds, “The PC-12 can land at smaller airfields often closer to the intended origin and destination, which can offer additional time savings.”

Keeping in mind that business doesn’t cease during travel, Pilatus PC-12s come equipped with plenty of privacy to conduct meetings in the air. Similar to its leisure flights, Tradewind’s business accommodations include comfortable air-conditioned cabins, leather seating, writing tables, and complimentary drinks and snacks, along with additional catering on request.

“Our clients who have flown the Pilatus on leisure trips have seen the efficiency first-hand, and many have started to apply the same benefits for their business trips,” says Zipkin, who expects Pilatus PC-12 business travel to continue its upward swing.

To learn more about using private charter as a business tool, please visit: https://www.flytradewind.com/private-charter/business/

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