How to Get to Anguilla

While each island in the Caribbean boasts its own singular personality, many visitors agree that there’s something particularly special about Anguilla. Lined with 33 white-sand beaches and surrounded by shimmering turquoise waters, this sought-after British territory is a serene paradise where friendly Caribbean vibes meet barefoot luxury.

As one of the Caribbean’s most laid-back (yet upscale) destinations, there’s an effortless ambiance to the enclave, nestled near St. Martin and St. Barths and stretching just 17 miles long, three miles wide. Better yet, what it lacks in size it makes up for in charm: Anguilla is home to some of the Caribbean’s most coveted dining destinations, beachside resorts, and leisure experiences.

Here’s how to get to Anguilla, and the best ways to discover all that this welcoming Caribbean haven has to offer.

How to Get to Anguilla

Even as one of the region’s hidden gems, Anguilla is surprisingly easy to access via Tradewind Aviation. Tradewind offers regularly scheduled shuttle flights from December through April, departing from San Juan, Puerto Rico.

San Juan can be easily reached from the mainland by both commercial and private flights, and given its status as a U.S. territory, the customs and immigration process for American travelers is a breeze. After your arrival at the San Juan airport, a private lounge for Tradewind passengers awaits with refreshments and WiFi to enjoy before your journey to Anguilla. For an even more seamless travel experience, opt for the exclusive VIP Meet-and-Greet service to help facilitate a smooth transfer between flights.

Serviced by a fleet of Swiss-made Pilatus PC-12s (featuring air conditioning, a pressurized cabin, and plenty of luggage space), unwind on your flight with complimentary snacks and refreshments including wine and beer before stepping into Anguilla’s salty, reinvigorating air. 

For a more direct route, Tradewind private charter flights can also be arranged from the U.S., Puerto Rico, the U.S. Virgin Islands, and Antigua. (Longer journeys, such as from the mainland U.S., are offered on Tradewind’s fleet of Citation Jets.) 

Where to Stay

Photo: Quintessence Hotel

Anguilla offers a host of luxe properties to call home during your Caribbean retreat. One of the island’s most iconic properties, the Belmond Cap Juluca, offers romantic, Moroccan-inspired décor and world-renowned service across 179 pristine beachfront acres. For a tropical boutique hotel experience, stay at Zemi Beach House, set on Anguilla’s famed Shoal Bay Beach and featuring the island’s celebrated Rhum Room.

Malliouhana (of the Auberge Resorts Collection) is another favorite — this lush hideaway on the northwest corner of the island beckons with its modern glamour and spectacular views of Meads Bay. The sleek, sophisticated Four Seasons Resort and Residences Anguilla is also a chic option in the area, with its 181 accommodations brought to life by sought-after interior designer Kelly Wearstler.

Meads Bay is also home to Frangipani Beach Resort, an intimate boutique property boasting 19 luxuriously appointed rooms. Overlooking a stretch of pristine white sands and expansive turquoise waters, the property blends island adventure (think complimentary motorized and non-motorized water sports) with blissful relaxation.

Along the curve of Rendezvous Bay, the CuisinArt Golf Resort and Spa also caters to high-end travelers. As its name suggests, the resort is especially known for its gourmet persuasions (such as fine-dining opportunities, a hydroponic farm, and cooking classes), and it’s also home to the island’s only golf course, designed by Greg Norman.

Finally, housed in a tropical mansion with just nine suites, Quintessence Hotel (fondly known as The Q Hotel) offers a secluded escape into ultimate luxury. Tradewind travelers will also receive a $150 dining credit at the hotel, as well as complimentary VIP Meet-and-Greet service for your connection at the San Juan airport.

Where to Dine

Photo: Cipriani Anguilla

Lauded as the culinary capital of the Caribbean, Anguilla’s array of fine island dining outposts is second to none. In a lovely, light-hued setting in Belmond Cap Juluca, the romantic Pimm’s serves upscale takes on Caribbean dishes, while the resort’s Cip’s by Cipriani is the perfect destination for a fine Venetian lunch by the beach (best paired with a glass of crisp rosé).  

Or, discover the meaning of “Cuisine of the Sun” at Veya, a highly rated island mainstay featuring a creative menu of Caribbean, Moroccan, and Asian cuisine from its treehouse-inspired perch. There’s also the acclaimed Jacala Beach Restaurant — though it’s adopted an unassuming online presence, it’s still considered one of the island’s top purveyors of French-influenced island fare.

For a more casual bite, head to the well-loved Straw Hat, featuring a seasonally driven and locally sourced menu within Frangipani Beach Resort. And because no visit to the Caribbean is complete without a visit to a charming beach hut, stop by the Sunshine Shack on Rendezvous Bay beach for a true taste of the local flavor.

What to Do

Photo: Quintessence Hotel

As gentle azure waves lap over pristine sands, there’s no question that Anguilla’s beaches are some of the best in the Caribbean. With 33 of them, it’s near-impossible to get your fill of each one on a single trip, but the spectacular Shoal Bay East can’t be missed — it’s often considered one of the most beautiful stretches of sand in the world. 

Beyond the beach, there are plenty of opportunities to discover the colorful sea life brimming beneath the ocean’s surface with a scuba diving or snorkeling excursion. Other water sports, such as paddleboarding, kitesurfing, windsurfing, and fishing are also popular, though sailing may take the crown as the island’s favorite aquatic pastime.

Back on land, Anguilla offers an array of charming boutiques ranging from local craftsmanship to curated luxury. The island’s top resorts also offer uniquely serene spas, though the Zemi Thai House Spa may be the most spectacular — the 300-year-old Thai house is a holistically inspired sanctuary for rejuvenating treatments, elevated wellness offerings, and more. 

Of course, the ultimate activity on Anguilla may just be, well, nothing. After all, there’s no better way to soak in the island’s relaxed splendor than dozing off under the sun while simply enjoying this slice of Caribbean paradise.

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Tradewind Aviation runs regularly scheduled shuttle flights to Anguilla from San Juan, as well as private charters to and from Anguilla from the continental U.S., Puerto Rico, the U.S. Virgin Islands, and Antigua.

48 Hours in Montreal

From its cobblestoned streets and Gothic Revival cathedrals to modern architecture and bohemian culture, Montreal is where contemporary influence meets European charm. This French-Canadian metropolis is home to a somewhat unlikely blend of old and new, paving the way for the city to become one of the country’s liveliest destinations for locals and visitors alike. 

Home to a buzzing art, music, and of course, food scene, Montreal is considered Canada’s unofficial cultural capital. It’s also known for its robust calendar of events and festivals that take place throughout the year (you’re nearly guaranteed to stumble upon at least one during a stroll through the city).

Explore this Québécois island on the Saint Lawrence River via a seamless Tradewind charter flight. Just north of the Vermont border, it’s easily accessible for a quick weekend trip, and there’s plenty to discover no matter when you visit — colorful leaves await during autumn, while winter is worth bundling up for to experience the city’s wonderfully festive atmosphere.

Here’s how to best take in the city during a 48-hour jaunt.  

Friday

Photo: Eva Blue

Fly into Montréal-Pierre Elliott Trudeau International Airport in the afternoon and make your way to the Old Montreal neighborhood, or Vieux-Montréal. The moniker rings true — the city began here when French settlers founded it nearly 400 years ago as Fort Ville-Marie, so it’s older than the country of Canada itself. And with its quaint cafés, bustling squares, and historic markets, it’s the closest thing you’ll find to Paris on this side of the Atlantic.

Check into Hotel William Gray, two 18th-century buildings (formerly a merchant’s house and a warehouse) combined to create Montreal’s trendiest luxury boutique hotel. While its stone white exterior is reminiscent of the area’s past, inside, the design is cosmopolitan all the way.

Photo: Hotel William Gray

After admiring your chic weekend accommodations, there’s no time to waste in beginning your exploration. Head straight to Basilique Notre-Dame, one of the city’s most breathtaking attractions, before its visiting hours end at 4:30pm. The gothic façade and stained-glass windows of this 19th-century church in Old Montreal offers a glimpse into the city’s rich past, along with the bell in the Western tower. The heart of the church is arguably its ornate organ, which dates back to 1891, located in the opulent chapel at the back of the church.  

Photo: Alain Régimbald

Spend the remainder of the afternoon rambling around the charming neighborhood (as the oldest street in the city, the pedestrian-only, lamp-lit Rue Saint-Paul feels particularly European). For dinner, make a reservation at the well-loved BARROCCO, a rustic, romantic French restaurant incorporating Italian and Spanish influences into its menu. Or, head to Le Garde-Manger to choose from their ever-changing blackboard of indulgent dishes crafted by celebrity chef Chuck Hughes (served in a cool, always-happening space).

End the evening with a nightcap at Terrasse William Gray, the hotel’s rooftop lounge offering creative cocktails and panoramic views of Place Jacques-Cartier, the St. Lawrence River, and Montreal’s Ferris wheel at the Old Port.

Photo: Hotel William Gray

Saturday

Photo: PixupMTL

No trip to Montreal is complete without a visit to Mount Royal, the hill after which the city is named. Parc du Mont-Royal was designed by Frederick Law Olmsted, the landscape architect who also created Central Park, and features lush forested areas, Beaver Lake, two cemeteries, and more. The chalet at the top offers a breathtaking observation point for visitors to overlook all of it, as well as the surrounding city. A network of winding trails allows you to hike around the mountain, or take the stairs for a more direct path to the views found at the mountain’s summit.  

After an hour or two immersed in urban nature, brunch is calling. The nearby area Le Plateau-Mont-Royal (or simply Plateau) is one of the city’s hippest neighborhoods, offering an array of shops and bistros along its tree-lined streets. Situated on L’Avenue du Mont-Royal (the area’s main street), quirky diner L’Avenue serves brunch classics in a funky, colorful space. For something lighter, see what all the fuss is about at St-Viateur Bagel Shop, an iconic storefront that’s said to give New York bagels a run for their money (Montreal bagels are boiled in water with honey, making them a bit sweeter).

Photo: Alice Gao_Commission Canadienne du Tourisme

Continue on to the creative, artsy Mile End neighborhood, often referred to as the city’s very own SoHo. You’ll find trendy boutiques and vintage stores around every corner here, and keep your eye out for stunning street art as you pop in and out of shops.

To round out your afternoon with some R&R, head back to Old Montreal and schedule a visit at Bota Bota, a tranquil floating spa anchored at the Old Port, offering an array of rejuvenating baths and treatments. Or, go straight back to Hotel William Gray to experience the warm quartz massage beds, Himalayan salt room, and experiential showers of their underground spa, rated one of the best in the city.

Photo: Ève-Marie Bourget

Sit down for a handmade pasta dinner at Da Emma, a warm Italian space located (surprisingly) in what was Montreal’s first women’s prison. For a more modern vibe, book a table at Le Serpent, one of Montreal’s top restaurants, serving Italian cuisine as well in a chic industrial setting.

If you’re up for it (particularly after an evening of bar-hopping or perhaps theatre tickets), be sure to save room for a traditional Montreal pastime: late-night poutine. Greenspot and Chez Claudette are both worthy destinations to get a taste of the Canadian classic in all of its gravy, cheese curd-smothered glory.

Photo: James Brittain

Sunday 

Photo: Denis Farley

Cap off your weekend by immersing yourself in the arts in true Montreal fashion. The Montreal Museum of Fine Arts is one of Canada’s (and North America’s) most often visited museums, featuring both permanent collections and roaming exhibitions from the world’s most esteemed artists. Spend your morning perusing the works on display, wandering among its five unique pavilions as well as the outdoor Sculpture Garden.

After two days of exploration, head home on your Tradewind charter flight on Sunday afternoon. By evening, you’ll be looking back on your weekend at the dinner table — and likely already planning your next escape to this charming cultural mecca. 

Photo: Loïc Romer

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

Featured Photo: Eva Blue

How to Get to St. Barths

Tucked among the Lesser Antilles islands 1,200 miles southeast of Miami, there’s an exclusive slice of Caribbean paradise with all the sophistication of a European-style retreat. Offering a one-of-a-kind ambiance that’s both laid-back and chic, the enchanting enclave of St. Barths beckons with its ultra-luxe boutique shopping, five-star resorts and hotels, fine French gastronomy, world-class watersports, and unparalleled natural splendor.

For those looking for a taste of this extraordinary destination, here’s how to get to St. Barths, along with an inside look at the unforgettable experiences that await.

How to Get to St. Barths

A stress-melting trip to paradise should be seamless from start to finish. Connected by virtually every major airline, book a transfer that’s both convenient and luxurious with Tradewind Aviation, which offers regularly scheduled shuttle flights to St. Barths from San Juan and Antigua. Private charters from the continental U.S. are also offered via Tradewind’s fleet of Pilatus PC-12s and Citation jets.

No matter which option they choose, travelers will enjoy a private pre-flight lounge, a VIP guided transfer option, and a comfortable flight complete with ample luggage room, air conditioning, and complimentary onboard snacks and refreshments, including beer and wine.

When flying overhead, the scintillating magic of St. Barths can first be felt as the island emerges from the sea in a spectacular heap of rolling verdant hills freckled with whimsical red-roofed cottages. Spread in the shape of a horseshoe across eight square miles, the volcanically-formed isle is roughly the same size as LAX — yet with its gently swaying palms, shimmering turquoise waters, and sun-drenched beaches, St. Barths couldn’t present more of a contrast.

The magic continues just after touching down at the iconic Rémy de Haenen Airport and opening the plane’s passenger door, when the island’s palpable energy floods in with the sea salt breeze. As visitors step onto the tarmac, they are greeted with a vibrant soirée of pastel colors declaring themselves in aqua blues, sea greens, canary yellows, and imperial reds.

The Beaches of St. Barths

The diverse coastline of St. Barths features no less than 14 swimmable beaches, boasting pristine ribbons of soft powder-white sand and impeccable aquatic conditions. It’s little wonder, then, that guests first set their sights on the island’s tide-washed shores.

As the most proximal beach to the airport, St. Jean Beach provides an inspiring setting to bask in blissful views or wade in the water while watching planes’ dramatic arrivals and departures from the adjacent runway strip. Within walking distance of the St. Barths capital of Gustavia, Shell Beach is an aptly named belt of sand replete with kaleidoscopic seashells and other unique natural treasures washed ashore by the heaving waves.

Beachgoers can also find shorelines that are secluded and serene — namely, the unspoiled crescents of Gouverneur, Saline, and Colombier beaches. Sheltered by their respective bays, each offers an idyllic respite for sunbathing, delving into the pages of a satisfying beach read, or snorkeling amid crystal-clear waters. Nestled on the southern coast, Saline Beach in particular provides an ideal vantage for soaking in vibrant Caribbean sunsets.

While watersport enthusiasts of all skill levels can find myriad opportunities to play in the seas surrounding St. Barths, Grand Cul-de-Sac’s shallow lagoon offers an ideally placid setting to develop a new hobby, such as kiteboarding, windsurfing, paddleboarding, kayaking, snorkeling, scuba diving, or sailing.

St. Barths Shopping

With more than 200 boutique shops scattered across Gustavia and beyond, St. Barths is a veritable mecca for extravagant shopping. As a favored retreat for celebrities and discerning guests, the island abounds with the latest fashions from some of the world’s most luxurious designer brands.

From bohemian-chic styles to jewel-studded opulence, the finest selections of shoes, jewelry, handbags, and clothing are all available for upscale perusing. Apart from the elegant designer offerings of Louis Vuitton, Prada, Dolce & Gabbana, Bulgari, and more, there are also plenty of posh products showcased throughout the island’s high-end boutiques.

Style aficionados would be remiss not to visit Libertine, a celebrated haven for sophisticated  lingerie, swimsuits, and beachwear, as well as Fabienne Miot, a locally owned jewelry shop creating island-inspired pieces from pearls and other precious stones.

St. Barths Restaurants

Brimming with pleasurable dining experiences, St. Barths provides a multitude of gourmet cuisine to satisfy and delight a variety of palates. Given the island’s distinct French influence, there is an almost-ubiquitous fusion of the country’s refined gastronomy and locally sourced tropical flavors. And with over 80 restaurants to choose from, visitors have no shortage of epicurean opportunities.

Set to breathtaking views of the Caribbean Sea, Restaurant Le Toiny curates an array of indulgent dishes from both land and ocean thanks to the imagination of Executive Chef Jarad McCaroll. Overlooking Gustavia, the acclaimed Bonito specializes in exquisite seafood selections as well as French-focused fare with a South American twist, all served with a side of sunset-primed panoramas. 

Guests craving fresh-made food to take along on a day of adventure will find plenty of delicious options at Maya’s To Go in St. Jean. Highlighting the day’s catch, the rotating beach-ready menu might include anything from grilled filet of mahi-mahi to wahoo ceviche infused with Caribbean-derived coconut and lime.

Nightlife on St. Barths

Whether visitors are seeking a sophisticated evening nightcap or the chance to fully let loose with bottle service, they’ll be pleased to discover St. Barths’ vivacious nightlife throughout its many trendy establishments.

Equal parts sushi restaurant and nightclub, Baz Bar dazzles after dark with live music and signature cocktails, including pineapple-infused French martinis and tropical Mai Tais. Nearby, the Rhum Room is tucked into the back of Quarter Kitchen. One of the island’s best-kept secrets, the stylish speakeasy purveys the best rum collection in the Caribbean.

Renowned for its Parisian atmosphere, Bagatelle has risen through the ranks to become another of the harbor’s most prized attractions with the help of boisterous resident DJ beats and French cuisine served late. Also pairing late-night eats with high-energy entertainment, Le Ti St. Barth amuses guests with burlesque dancers who remind patrons of the Moulin Rouge as they perform their routines on floor and tabletop alike.

St. Barths Events

A cultured crossroads of art, music, entertainment, and cuisine, St. Barths is home to a perennial roster of events throughout the year, which regularly attract droves of visitors from all corners of the globe.

Each January, the island plays host to a series of live performances from prominent international musicians during the St. Barth Music Festival, and when Mardi Gras rolls around in February, the streets explode with colorful costumes, body paint, and lively music during the annual Carnival celebrations.

With its immaculate sailing conditions, springtime in St. Barths is ideally suited for several prestigious competitions, including the three-day invitational Bucket Regatta (which draws the world’s most luxurious superyachts), the beloved Les Voiles St. Barth, and the West Indies Regatta, a show of schooners and sloops paired with a spirited market on Gustavia’s harbor to commemorate the bygone days of Caribbean trade.

As the high season commences in the fall, France’s top culinary talents gather for the St. Barth Gourmet Festival, a weekend brimming with enticing multi-course menus meant to delight and capture the essence of the island.  

After visitors have experienced this Caribbean enclave and all it has to offer, they can make their way back to Rémy de Haenen Airport for an easeful Tradewind departure back home.

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Tradewind Aviation runs regularly scheduled shuttle flights to St. Barths from San Juan, St. Thomas, Antigua, and Nevis, as well as private charters to and from St Barts from the continental U.S and Caribbean.

The Art of the Surgical Strike with Next Level Watersports

In most scenarios, telling someone to ‘go fly a kite’ may be ill-advised — but in the world of extreme kiteboarding, such a suggestion constitutes just another day at the office. Whether adventure seekers have already mastered the sport or they’re just getting their toes wet, the seasoned professionals at Nantucket-based Next Level Watersports can help deploy a memorable excursion based on where the weather is primed for kiteboarding.

When the absolute best conditions align, Next Level partners Jon Beery and Jake Hoefler can be found chasing them, finding the sweet spots to share with anyone who wants to ride.

“Basically, we love when ferries get cancelled, because that means big weather is here,” explains Beery, whose ears — along with Hoefler’s — tend to perk up whenever a storm is brewing over the Atlantic. “So when everyone is trying to get off Nantucket, we’re trying to bring people in.”

A wind-dependent sport, extreme kiteboarding is best served with a side of intense elements, so the pair has developed a plan to bring the sport’s enthusiasts directly to the action. With Next Level Watersports’ Surgical Strike Club, discerning kiteboarding clients can get almost-guaranteed exposure to a safe, yet thrill-inducing setting to ride across the waves. Lucky for private aviation travelers in the Northeast, this singular experience is only a Tradewind Aviation flight away.

“For a lot of our clients, their scarcest resource is their time — so they want to ride the best conditions in the best spots,” Beery says. “They want to know that the wind and the weather is going to line up so they don’t fly somewhere and end up sitting on a beach doing nothing. That’s when we came up with the concept of Surgical Strike Club.” 

When a weather window opens, the early stages of a Surgical Strike trip spur into motion as Beery and Hoefler keep a close eye on the forecast and contact their portfolio of kiteboard-loving clientele. If a developing storm looks like it will deliver prime conditions, the pair kicks into full throttle with securing reservations, booking flights, and preparing gear for the impending expedition. And if clients can commit to a last-minute kiteboarding adventure, they should expect to leave their jobs behind for a few days in favor of an action-packed playground of sweeping gusts and roiling waves.

“We like to say that kiteboarding is the new golf,” says the 29-year-old Hoefler, who’s been dabbling in the sport since he was 12. “Our clients are highly motivated, successful individuals who like pushing themselves, and it’s another way to do that outside of the office, an activity that clears their head for getting back to work.”

While Nantucket is especially conducive to Surgical Strike trips in September when the region abounds with kite-friendly winds, Next Level Watersports also runs excursions in the wintertime months to chase the trade wind breezes throughout the Caribbean, particularly around Turks and Caicos, the Grenadines, and Antigua.

The kiteboarding company generally has two types of clients: those from the Northeast seeking an executive weekend with a quick turn-around in order to make it back home for family dinner on Sunday night, and then those who are able to take more time off in order to explore the world’s premiere kiteboarding spots.

“They can go to a place like Fiji,” says Beery. “The possibilities are endless when you have a little more time.”

No matter which type of outing they choose, kiteboarders of all abilities are in good hands with the experts at Next Level, who specialize in curating the kinds of trips that are not soon forgotten.

“Kiteboarding is this amazing sport with incredible freedom where the wind is powering you and you can fly around, jump, ride extremely shallow water, and get out and see all these new areas,” Beery says. “It feels a lot like you’re riding powder. Anyone can do it, but you have to work through the whole learning curve and once you have learned, you can basically go anywhere in the world and explore.”

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As a partner of Tradewind Aviation, Next Level Watersports offers premiere kiteboarding opportunities from Nantucket with an emphasis on convenience and luxury. Tradewind also offers regularly scheduled shuttle flights to Nantucket from late April through early December, as well as private charters year-round.

All photos courtesy of Next Level Watersports.

Celebrating a Tradition of Cranberries on Nantucket

Think Nantucket, and, most likely, images of windswept seascapes, gray shingled cottages, historic lighthouses, and quintessential New England sailboats come to mind. But the very Cape Cod island people tend to associate with all things maritime also has some interesting agricultural history. It’s home to the once-largest contiguous cranberry bog in the world, and now the largest certified organic cranberry farm in the United States. 

Here, we delve into Nantucket’s cranberry-harvesting past and present, plus an inside look at the ultimate way to immerse yourself in the Ocean Spray world: the Nantucket Cranberry Festival on Saturday, October 12th.

Once Upon a Nantucket Cranberry Bog

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Native to the northern latitudes of North America, cranberry shrubs were first cultivated in the early 1800s in none other than Cape Cod, in the blink-and-you’ll-miss-it town of Denis. Centuries prior, the tart red berries had been used for food and dye by Native Americans and the Pilgrims. By the 19th century, cranberries had become quite the delicacy for use in sauces and desserts, and a fledgling Massachusetts housed idyllic wetlands for growing this now-trendy superfood.

Nantucket jumped on the cranberry farming bandwagon in 1857 with the formation of the Milestone Bog in the center of the island. Many more bogs followed, but it was Milestone that soon made history as the largest contiguous cranberry bog on the planet, measuring at a whopping 234 acres.  

As cultivation and irrigation techniques improved, Nantucket farmers figured out that bigger isn’t always better. Once ripe, the berries are harvested by flooding the sunken agricultural lands and allowing the berries to float to the water’s surface. Dividing larger bogs into smaller parcels proved far more efficient for collecting the so-called “red rubies.” With this in mind, Nantucket developed dozens of smaller bogs, and soon cranberry production proved a strong contributor to the island’s growing economy.  

Nantucket’s Present Day Cran-Culture

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In the second half of the 20th century, little Nantucket’s cranberry industry became no match for the commercial production that had emerged in Wisconsin, Quebec, and mainland Massachusetts. In August 2019, it was announced that one of the island’s two remaining cranberry operations, the 37-acre Windswept Cranberry Bog, would cease production and transition back into a natural inland wetland — leaving Milestone as Nantucket’s last bog standing. 

Thankfully, under the watchful eye (and ownership) of the Nantucket Conservation Foundation, Milestone’s current 195-acre, 24-bog cranberry excess (and the two million pounds of berries produced there) is here to stay. To ensure this, Milestone has set itself apart from its commercial competitors by becoming exclusively organic, branding Nantucket Conservation Foundation the largest certified organic cranberry grower in the United States. Additionally, in 2004, the Foundation began an annual, one-day Cranberry Festival to raise awareness about Nantucket’s agricultural heritage. Fast-forward to present day, and this adorable festival, which takes place each year over Columbus Day weekend, is one of the most anticipated events of the fall season.

The 16th Annual Cranberry Festival

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The 16th annual Cranberry Festival will be held at Milestone Bog on Saturday, October 12th, 2019, from 11am to 4pm. This dynamic affair takes place at the height of harvest season, meaning the land will be glowing with abundant picture-perfect red rubies. It also means that you can strap on a pair of rubber waders, grab a rake and wade through a bog—just like the guys in the Ocean Spray ads. Visitors can either partake in the harvest by raking the berries on the surface, or simply go in a for a few fun pictures.

But, of course, there’s so much more to this festival than a great Instagram post. Guests can feast on amazing cranberry dishes from local vendors, such as the cranberry pecan bread from Wicked Island Bakery, cranberry pies from Bartlett’s Farm, cranberry fudge from Aunt Leah’s Fudge, and fresh-pressed juice from ACK Fresh. There are also opportunities to learn about traditional versus organic techniques from professional farmers through one-on-one discussions and guided tours. Plus, you can check out the operational, antique berry bouncing machine (as it sifts berries) and browse a very cool collection of antique tractors.  

Children are sure to love the hayrides along the bog as well as other kid-friendly happenings, including a petting zoo, face-painting, sack races, and meet-and-greets with some of the fluffy sheep living at Milestone (who are supervised by the resident Border Collie, Rem). Meanwhile, adults will appreciate the live music, you-pick areas (for taking a few pounds of the good stuff home), harvesting demos, and self-guided walking trails through the bog and surrounding autumn scenery. This off-the-wall themed festival is a great way to immerse yourself in all things cranberries — with the exception of a vodka cranberry cocktail in hand.

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Tradewind offers regularly scheduled shuttle flights to Nantucket from late April through early December, as well as private charters year-round.

Featured Photo: J. Greg Hinson

The Culinary Outposts of Northern Vermont

A featured story by David Gould, a renowned travel writer and former Executive Editor of Travel + Leisure Golf.

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You can stroll into most gourmet shops these days and purchase Himalayan pink salt blocks, mined in Pakistan from deposits more than 100 million years old. But in the late 1990s, when I was introduced to these epicurean wonders, they weren’t so well-known.  

The setting was a chef’s-kitchen dinner for a small group of food critics and travel writers in northern Vermont. Our host hand-grated some of his ultra-pure salt crystal for us, as the food critics smiled discreetly. From that night forward, I was aware that traveling due north in the Green Mountain State didn’t mean you were leaving civilization behind — not hardly.

Northern Vermont is something of an epicurean hotspot, with three main towns holding court as its culinary centers: Stowe, Burlington, and Middlebury (and their surrounding areas). Explore the best of each on a three-stop itinerary via Tradewind Aviation.

Fly into Stowe on a private charter or shuttle flight (resuming in December), and you’ll soon find yourself on a descent into Morrisville–Stowe State Airport, staring at the giant’s-face-in-profile view of Mt. Mansfield’s 4,300-foot peak, complete with its forehead, nose, lips and chin. May sound corny, but if you hike up there it’s likely you will use those features to navigate. 

Also out the aircraft window should be glimpses of Montreal, just 100 miles to the north and a steady source of prosperous, urbane tourists who know fine dining when they come upon it. Their influence, combined with the luxury vacation-home culture generated by Stowe and other ski resorts, generates considerable demand for cool things to see, do, and dine upon.

Photo: Plate

In the village of Stowe and down Route 100 at the eponymous resort, there’s no shortage of options for where to dine. Inside six-year-old Plate, on the village’s Main Street, you’ll find locals and visitors alike in comfortable booths of slate gray with polished wood trim under sparkly pendant lighting. The menu, atmosphere, and execution all adhere to lofty standards at Plate — presentation of the dishes is artistic, though never precious. There are small plates for the foodie who wants to sample and savor, but also generous portions of Curry Pork Loin or Jamaican Jerk Half Chicken, if you’re up for it. Reservations are suggested. 

The decor and branding of highly popular Doc Ponds may seem reminiscent of legendary local jam band Phish and the creative-slacker element found in any prominent ski town. But then you’ll consider how much discipline and devotion it takes to make an ambitious restaurant concept succeed the way this one has. A scan of the Doc Ponds menu shows comfort recipes wherever you look, but visually and gastronomically it’s a refined experience (don’t be surprised if post-graduate discussions of beer and how it’s produced arise).

Even during a tour of northern Vermont is by plane, the gondola ride up to the Cliff House Restaurant at Stowe Mountain Resort should still be a kick, and the wall of windows inside this chalet-style eatery offer breathtaking views of inspiring panoramas. Logically enough, the restaurant serves lunch only, except for the dinner opportunities afforded via a special Summit Series schedule of themed evenings.

Photo: Stowe Mountain Resort

A quick Tradewind flight over to Burlington International Airport is next, transferring you from an alpine backdrop to an urban one. As you approach the Champlain waterway, you’ll get a chance to discover, as I have, that the prairie-like parts of the state are as visually poignant as the mountainous regions.

It was here in greater Burlington, by the way, that I received my introduction to the dazzling pink salt block. That evening’s intimate dinner was hosted by a first-class hostelry now known as The Essex, Vermont's Culinary Resort & Spa. Conditions are right to make Burlington an outpost of the so-called “culinary vacation business,” and the location of The Essex next door to the prestigious New England Culinary Institute is emblematic of the collaborative energy that keeps the local foodie scene humming.

Hotel Vermont, with its plain-country name contradicting its chic sophistication, is an obvious choice for lodgings. The hotel’s bar and restaurant, Juniper, is visually appealing with its copper, hardwood, and gleaming glassware. There’s even an outdoor space with a fire pit and Adirondack chairs. Order the Lake Champlain Perch with frisée, malt vinegar, shallots and hazelnut oil. In the same neighborhood are two other top-rated Burlington restaurants, Hen of the Wood and Bleu Northeast Seafood. These three award-winners are mainstays of what’s considered the Cherry Street dining scene, and empty tables are rarely spotted up and down the boulevard.

Photo: Marshall Webb

The Inn at Shelburne Farms, the centerpiece of a 1,400-acre preserve along Lake Champlain, is a destination all its own. You get here from Burlington via Route 7 on a ride that is quite short, especially given that it takes you back in time a century or two. To enjoy dinner here you have to make reservations a month in advance. The rooms are exquisite, but the place has no central heating or air conditioning. Cuisine doesn’t get any more farm-to-table than the ISF, but if you simply want the vibe of the place, wander by to watch the artisan cheesemaking operation. It’s housed in a cathedral-like barn and produces cheddar that’s almost too good to share with your house guests, every block of it made from raw milk produced by the Brown Swiss cows that roam the acreage in country contentment. 

The third stop on your tour brings you into Middlebury State Airport, a few miles southeast of the the town’s central business district. Part college town, part county seat, Middlebury is an easy place to feel comfortable in as soon as you arrive — all the more so if you drop by the spirited Two Brothers Tavern on Main Street. You can try their cheddar ale soup, grilled Spanish octopus or the popular comeback burger, made with comeback sauce and offering a taste of Southern-style cooking in the north country. Sabai Sabai Thai Cuisine is a can’t-miss stop for high-quality Asian food — it’s known for a squid specialty called khan soi. 

Drive 15 minutes up Route 7 and you'll come upon the little city of Vergennes, named for a French nobleman who helped swing the American Revolution our way. On Green Street you’ll find Bar Antidote and its pub-crawl pairing, Hired Hand Brewing. The location is hard to miss, given the retro, better-living-through-chemistry logos of these two establishments.

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We’ve known for quite a while that this part of Vermont attracts chefs and innkeepers who could be working in the big cities, but come here instead for the lifestyle. But interestingly, a Vermont farm kid, Ian Huizenga, is currently outdoing most (if not all) of those who parachuted in. Huizenga is the chef and brewer behind Antidote and Hired Hand. He was named Vermont Chef of the Year in 2017, but his talents extend beyond cooking and beer-crafting to interior design and the artistry that goes into his branding and graphics.

Hired Hand would be part of the farm-to-glass movement, if there were enough microbreweries using local ingredients to actually call it a movement. The sourcing effort Huizenga makes to hyper-localize his product is tireless, but worth it. Downstairs from the brewpub, Bar Antidote is where locals and visitors gather to dine on grilled Vermont flat iron steak served on roasted mushroom toast and crispy-crust pizzas — also made with locally sourced fixings.  

If you find that you keep extending your visit, be advised that people have become residents of this region very gradually — without ever consciously deciding they would move here. 

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Tradewind will offer shuttle flights to Stowe beginning in December 2019, and also offers charter flights to Stowe, Burlington, and Middlebury year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

Featured photo: Mark Vandenberg