Anguilla: A Luxury Enclave with Local Character

Anguilla: A Luxury Enclave with Local Character

Blending sumptuous resorts with low-key Caribbean charm, Anguilla is a paradise for travelers seeking to get off the grid without sacrificing luxury. Renowned as the culinary capital of the Caribbean, the secluded island offers five-star cuisine overlooking some of the most beautiful white sand beaches in the world – from which divers can explore centuries-old shipwrecks and expansive coral reefs amongst the local marine life.

Brilliantly white oceanfront hotels and villas contrast historic buildings and clapboard shacks, lending the island an authentic, easy ambiance not often found in luxury travel destinations.

And on the beach at Sandy Ground, the cultured tradition of boat racing draws spectators as locals race around the island – just 17 miles long by 3 miles wide.

Getting There

Tradewind Aviation flies scheduled one-hour shuttles to Anguilla from San Juan International Airport, as well as private charter flights from destinations throughout the Caribbean.

Best Time to Go

Ideal weather between mid-December and mid-April drives the high season, though flexible travelers can take advantage of lower rates as temperatures rise between May and August. Fall may be equally beautiful on the island, but many of the hotels and restaurants close down and hurricanes can affect travel plans with little notice.

Luxury Hotels and Private Villas

  Image: Cap Juluca

Image: Cap Juluca

Cap Juluca: Spanning 179 acres overlooking on Maundays Bay, Cap Juluca is unmistakable with its Moroccan-inspired villas (15 housing 69 guestrooms) and sense of romantic tranquility. The grand resort features many beautiful open-air spaces amidst its three restaurants, world-class spa, fitness center, and library. At the height of luxury, the Jonquil Suite highlights unparalleled ocean vistas and a private freshwater infinity pool.

Malliouhana: Perched on a lush coastal bluff on the western side of the island, Malliouhana by Auberge Resorts Collection offers luxury boutique accommodations in 44 stunning rooms and suites. The pristine beaches of Meads Bay and Turtle Cove are just steps from your retreat, where modern amenities blend with the warm, gracious charm of the Caribbean. And through March, you and your loved one can indulge in a romantic getaway that includes champagne and truffles, spa therapy, a private dinner on the beach, and charter flights with Tradewind – courtesy of Malliouhana’s Love is in the Air package.

CuisinArt Golf Resort & Spa: Gourmet cuisine with Caribbean flair takes center stage at the sumptuous CuisinArt Golf Resort & Spa. Nestled in the curve of Rendezvous Bay, the luxury resort features acclaimed restaurants, cooking classes, and wine tastings along with 98 suites and private villas, Venus Spa (try the aquatherapy), and an 18-hole championship golf course designed by Greg Norman.

The Villas: Anguilla is home to a number of spectacular villas, from extravagant retreats for 50 (Sheriva Estate) to getaways that set the stage for tranquil seclusion (Little Harbor Estate and Nevaeh, among others).

Authentic Caribbean Cuisine

Pimms: The elegant, columned dining room at Pimms at Cap Juluca offers some of the most delicious European and Caribbean fusion cuisine on the island. Indulge in Anguillan crayfish and other delicacies while enjoying the award-winning wine list and views of Maundays Bay.

Veya: For 10 years, Veya has been delighting palates with their self-dubbed cuisine of the sun. The acclaimed eatery features exotic flavors from around the world such as Chef Carrie Bogar’s grilled jerk spiced tuna and her tamarind glazed roast.

Jacala Beach Restaurant: In an open-air dining room overlooking the coastline, Jacala Beach Restaurant invites guests to dine on French cuisine in beautiful presentations, like olive oil poached mahi-mahi with curry-lemongrass sauce.

  Image: da'Vida

Image: da'Vida

da’Vida: Spectacular local and international fare come together at da’Vida, one of the island’s best beachfront eateries. The restaurant (and spa) has casual burgers, sandwiches, and wraps at the bar as well as elegant dinner menu items like ginger teriyaki sea scallops.

What to See and Do

Thirty-Three Beaches: Shoal Bay East is considered to be one of the most beautiful beaches in the world, and the other 32 beaches are well worth the visit too, from Meads Bay to Sandy Ground to Cove Bay.

Sailing and Other Watersports: Offshore cays and secluded shorelines are all within a short sailboat or glass-bottom boat ride, and make sure to bring your snorkeling and diving gear for the chance to see sea turtles, parrot fish, and blue tangs. With seven marine parks and nine shipwrecks, Anguilla is a diver’s haven (we recommend the underwater cavern Prickly Pear Cays), and you can also try your hand at kitesurfing, windsurfing, and fishing.

Historic Landmarks Meet Local Art: A walk through Anguilla’s small towns will lead you to a number of quaint art galleries, including Cheddie’s Carving Studio where you can shop for driftwood sculptures. History buffs will also enjoy exploring the island with destinations like the Wallblake House, the oldest structure on Anguilla built in 1787, and St. Gerard’s church, an open-air place of worship with a ceiling shaped like a ship’s hull.

Annual Traditions: Regattas, golf tournaments, seasonal festivals, and concerts on the beach define the annual gatherings on Anguilla, but most anticipated of all are the boat races held during spring and summer. Become a spectator at the Anguilla Day Round the Island Race in May or the Champion of Champions race, held at the end of Boat Racing Week in August, for a true taste of island culture.

*Featured Image: Cap Juluca

Three Caribbean Islands for a Yoga Getaway

Three Caribbean Islands for a Yoga Getaway

The serene white beaches and lush landscapes of the Caribbean are restorative in nature, making them the ideal destination for deepening your yoga practice under the guidance of world-class instructors while seeking harmony in mind, body, and spirit.

From barefoot yoga on the beach to creative variations like paddleboard yoga, here are some of our favorite places in the Caribbean for an inspired yoga retreat – all easily accessible with Tradewind Aviation’s regularly scheduled shuttle flights.

St. Barth

On the stylish island of St. Barth, wellness goes hand in hand with your stay. Many of the leading resorts like Le Guanahani, Cheval Blanc, and Hotel Christopher offer transformative spa experiences and healthy cuisine, and when you request one of the local yoga instructors, they will come right to your hotel, villa, or yacht for private classes – and even customized private retreats.

Nanda Mortier, a native of the island, teaches her Vinyasa flow yoga using controlled breathing to move fluidly from one pose to the next (often right on the sun-kissed beaches). She is certified in Thai massage and Reiki (a Japanese technique for reducing stress and promoting healing) and can customize yoga classes for alignment, restoration, and prenatal requests.

Her collaboration with Elisa White, BODY+SOUL St Barth, is a wonderful option for a wellness retreat that incorporates yoga, conscious hikes, meditation, Janzu (water therapy), Reiki, and other healthful, healing experiences.

Another favorite on St. Barth is Yoga Vidya, a studio that highlights Iyengar yoga, which emphasizes correct alignment within each precise pose to build strength, stamina, balance, and flexibility. Rather than finding your own way in your practice, a highly trained Iyengar instructor actively corrects misalignments. And for an enhanced experience, you can set up a Yoga Intensive retreat that is personalized to your needs, in which you will stay in the instructor’s home or meet with her daily in your accommodation.

St. Thomas

 Photo: Bev Goodwine

Photo: Bev Goodwine

Charming, colonial style and stunning stretches of beach await in St. Thomas, a destination for yogis in search of a creative island practice. Perhaps the most well-known variation on the island is stand up paddleboard yoga, which tones core muscles as you try to maintain your balance on the water.

Marriott Frenchman’s Cove, just across from the luxury Frenchman’s Reef & Morning Star Marriott Beach Hotel, is home to SUP Yoga VI, where yoga enthusiasts can take scheduled paddleboard yoga classes or arrange for private classes on the beach of their choice. (Couples: try the partner paddleboard yoga.)

The modified Vinyasa flow style encourages a relationship with nature, because without the studio walls and a stable floor, you are completely immersed in the environment – an environment often brimming with sea life like the bay’s resident sea turtle.

Just up the coast, a completely different style of practice, and one that is unique in the Eastern Caribbean, can be found on the terrace of the historic 1500s villa Casa De Atelier and in other mobile locations throughout the island.

Designed by the creator of the aerial yoga fitness genre, Christopher Harrison, Point Wellness AntiGravity Aerial Yoga allows participants to stretch both the mind and body in stunning coastal settings. The location of Casa De Atelier contributes to its romantic, secluded ambiance, and guests staying in other villas have the ability to host the class if the structure allows for it. (Additionally, the studio holds classes at Gifft Hill School on the neighboring island of St. John after recently moving from the original Point Pleasant Resort location on St. Thomas.)

Puerto Rico

 Photo: Jorge Colon

Photo: Jorge Colon

Amidst the spectacular cuisine and colorful culture of San Juan, there is an enclave of yoga experiences to be found. Stay in an oceanfront resort like Condado Vanderbilt Hotel or La Concha and you won’t be far from the city’s best yoga studios (or a fresh coconut to follow your practice).

In Ocean Park, Ashtanga Yoga has been offering classes in the Progressive Ashtanga Vinyasa style with the goal of becoming more centered since the style’s founding 10 years ago. English and Spanish speakers will find a practice they enjoy with up to six classes some days, including beginner yoga, traditional Vinyasa yoga, nontraditional Rocket yoga, and open practice.

The owners will encourage you to stay for a week (or for a month), and if you take them up on it, you may want to look into their teacher training courses to further your yoga practice.


*Featured image: SUP Yoga VI

Skiing Stowe Like a Local

Skiing Stowe Like a Local

It’s peak season on Mt. Mansfield and Stowe Mountain Resort is brimming with winter sports enthusiasts enjoying yet another bluebird day in alpine Vermont.

Among them is Director of Mountain Recreation, Dave Merriam, who is innately familiar with the resort’s 40 miles of ski trails and 12 high-speed lifts (more mile-long lifts than anywhere else in the East).

Along with the breathtaking scenery, Merriam says, “I love Stowe because of its sustained vertical. At a lot of Eastern resorts, your way down is quite stepped, meaning it’s steep and then flat for a while and then steep and then flat. [Here] you really feel gravity.”

Merriam enjoys the mountain all season long – from a week or two before Thanksgiving to late April – but notes that late January and February may be considered the most ideal for ski conditions and that many visitors enjoy the lengthening days of March.


When it comes time to plan your route on the trails at Stowe Mountain Resort, Merriam has a recommendation that many Stowe regulars would agree with: “Follow the sun.”

The resort is split across Route 108, with the Over Easy Gondola connecting the two sides. Experienced skiers and snowboarders should start on the Mansfield side of the resort, which includes the infamous front four. “National, Liftline, Starr, and Goat are part of this wonderful front four experience,” says Merriam, “which is double-black diamonds [with] speed, a very sustained fall line, and vertical.”

“And on the shoulder of Mansfield, there is some wonderful cruising terrain – just great cruisers that dip and turn and roll with the terrain. They’re very classic Eastern skiing slopes. They are more intimate with the trees and so forth.”

The front four are serviced by the Fourrunner Quad, which has a 2,000-foot elevation change from base to top, and with very little sideways traffic, the runs flow smoothly all the way down.

In the late afternoon, when the front four begin to darken, head to the neighboring Gondola space on the other side of the river basin, where you will find the sun and the majority of the resort’s blue runs. (“The Gondolier and Perry Merrill are wonderful groomers – great cruising.”)


And to finish the afternoon, take the Over Easy Gondola to the Sunny Spruce side of the mountain in the southwest. The area is home to most of the resort’s green runs and features the ski and ride school, children’s center, brand new adventure center, skating rink, ski racing programs, and Stowe Mountain Lodge – the only ski-in, ski-out resort in Stowe. (The lodge has great packages like the Snow Day offer for discounted lift tickets and lodging.)

“One thing I love about the mountains in the East is they are quite intimate,” Merriam says. “When you’re in the Rockies, it’s big. In Stowe, you’re very close to everything.”

You can also stipple your day with runs through the resort’s freestyle terrain parks on the Mansfield side. The Mountain Triple lift will get you to the large terrain park with jumps and rails for experienced skiers and riders, the medium park, small park, and natural terrain park that is popular among families.

And experienced riders will want to try out Merriam’s personal favorite run, Hayride — accessible by the Fourrunner Quad. (“It’s a very steep, groomed run. It’s just wonderful.”)


Merriam also recommends arranging a lesson – which you can do at the ski school or through the concierge at Stowe Mountain Lodge for any skill level – and trying out equipment through the resort’s demo program, to find the best fit for your style both on the slopes and in the terrain parks. “There’s such amazing gear that makes powder skiing more enjoyable, really hard snow more enjoyable,” he says. “And trying out different gear is really fun in finding the right gear for the right conditions.”

When your day comes to a close, there is a host of wonderful après ski destinations nearby, including The Den, Spruce Camp Bar & Grill, and Skinny Pancake at Stowe Mountain Resort, and, on your way back to Stowe, the classic Matterhorn at the base of the mountain.

Best of all, with Tradewind’s regularly scheduled shuttle flights from New York and private charters from throughout the Northeast, it’s all just a short flight from home.


*All images courtesy of Stowe Mountain Resort

Tradewind Through the Eyes of a Four-Year-Old

Tradewind Through the Eyes of a Four-Year-Old

This is the story of a little girl who went on a big plane. Well, actually a little plane—a sleek gray Pilatus PC-12 from Tradewind Aviation, to be exact.

We followed along for the ride to see what it’s like to fly to St. Barth as a four-year-old. Sure, it’s great flying private when you’re a grown up, but it’s even better when you’re a toddler. Forget standing in line; here you are ushered to a private lounge at the San Juan airport, where there are lots of snacks and magazines.

And we all know what a pain it is to go through security and take your shoes off. Not here—the pilots give everyone on the flight extra-special attention. And when you’re 4, they’ll even let you sit in the front row, so that you can get the best inflight entertainment ever: a view of the pilots flying the jet.  

Join us as we follow along with this little girl on her very exciting journey.

The Story Behind New England’s Largest Wine Festival

The Story Behind New England’s Largest Wine Festival

There is a lot to like about James Carmody, the bluff Irish general manager of the Seaport Hotel in Boston, even over the phone. Here he is, one of the founders of the Boston Wine Expo—the largest and longest running wine festival in New England (always held over Presidents’ Day Weekend)—an unabashed guy from Dorchester ("You can hear it in my accent") whose mother discouraged alcohol, but who is now a wine lover, and he's laughing at the improbable success of the event.

He was among a small group, most of them from the Boston Oenophiles Guild, who started the event in 1991 as a Hail Mary. The Guild members were interested in putting Boston on the wine map and Carmody was, too—he came up through the food and beverage side of the hotel business—but he also had a slightly more urgent agenda: to create hotel traffic at a dead time of year. Who goes to Boston in February for fun? After all, Carmody was working at the Boston Harbor Hotel at the time (in the late 80s), and the hotel would actually have to lay off banquet staff and "hope they'd come back in the spring," he says. 

"Still, the vision was always to make The Expo, which takes place just down the street in the World Trade Center, into a championship game," he says. (The proof? People turn out even when the Patriots are in the championship—"Okay, they leave at four," says Carmody. "Why not?"). "But really only two or three of us believed we could make this happen when we started," he admits.

The other heart-warming aspect of The Boston Wine Expo is that it was all done on relationships—"a snowball rolling downhill," Carmody says. Guild members were enthusiasts and wine professionals, and they used their knowledge and relationships to bring winemakers to Boston in the dead of winter. Which is probably why the Expo, for all of the 200 vineyards and 1,800 wines that will show up and be poured next month, has, as its defining trait, a pleasing quirkiness.

The Wine Spectator New York Wine Experience is far grander and much bigger—an Inaugural Parade as opposed to the Expo's Memorial Day one. Carmody admits it, but even Thomas Mathews, Executive Editor of Wine Spectator, gives the Expo credit: "It began as a something of a drinkfest, but has evolved for the better. The quality of the exhibitors has significantly increased and the seminars are serious educational offerings showcasing top regions and wineries. The attendees are a broad cross-section, including consumers just beginning to learn about wine, seasoned collectors, and veterans of the trade."

The Boston Wine Expo is reasonably priced, as the goal has always been to "keep it accessible." Therefore the entry fee is just above happy-hour prices in Boston (this was a legal requirement, as well). But, of course, there are events (last year, a Pappy van Winkle bourbon tasting), seminars, and a private lounge, all of which cost more but are still not in the 1%-er category. The overriding spirit remains "to develop the next generation of wine drinkers as part of a healthy lifestyle," Carmody says, which was part of the founding vision. The other key phrase: "Offer a spirit of discovery."

So if you fly into Boston on Tradewind’s scheduled private shuttle over Presidents’ Day weekend, you get to sample some brilliant—and hard-to-find—wines at a sizable discount.

There's Château Picque Caillou, a stone's throw from Pape Clément and Haut-Brion, a wine that I bought when I was earning next-to-nothing as a magazine editor and that turned out to age brilliantly. André Shearer, head of Cape Classics, a pioneer importer of South African wines (and former fashion model), will be there. As will Bertani, a great Amarone house—"They just won't compromise," says Carmody—and Domaine des Baumard from the Loire Valley, whose Clos du Papillon is a fetish wine. "I saw an older bottle at a retail shop and bought it knowing nothing," says Carmody. "Then I called the distributor and bought the rest." (You gotta love this, right?)

Among the highlights of this year's Expo will be “The World of Sicilian Wine” seminar—taught by Master of Wine Bill Nesto—a vertical of Chateau d'Ampuis led by Fred Ek—distributor of hall-of-fame European winemakers (Guigal and Remoissenet, among them)—and a Riesling seminar.

Regarding the latter, Carmody is 110% himself in admitting "We all grew up on Blue Nun as the transition from pop [soda] to wine."

But he's grown up—matured, one might say—just like the Expo: "Riesling is probably the greatest food wine there is.”


Fly into Boston with Tradewind Aviation, offering scheduled shuttles and private charters from across the Northeast, including New York.

*All images courtesy of the Boston Wine Expo

5 Things to Try in Stowe this Winter

5 Things to Try in Stowe this Winter

While most visitors are familiar with Stowe for its world-class ski slopes and stunning mountain vistas, there are a number of lesser-known ways to experience the picturesque Vermont town when you fly with Tradewind Aviation from hubs in the Northeast.

Whether you prefer a long-standing, traditional festival or innovative new culinary establishments, plan to enjoy some of our favorite events and pursuits this winter—in between powdery ski runs, of course.

The Stowe Derby

  Stowe Derby; Photo:    Mike Hitelman

Stowe Derby; Photo: Mike Hitelman

In 1945, two expert skiers raced down Mt. Mansfield and into the village of Stowe in a personal competition. Today, the Stowe Derby is the oldest downhill and cross country ski race in North America, attracting hundreds of enthusiastic competitors to Vermont each winter. This season’s race, set for February 26, begins with 14 kilometers of downhill skiing followed by 6 kilometers on the flat Stowe Recreation Path and in the village. The total drop is 2,600 feet.

Competitors also have the option to undertake the 14-kilometer Fat Bike race or the Fat Meister, which combines the ski derby and the Fat Bike race and is only recommended for serious outdoorsmen. In any case, both competitors and viewers can enjoy a spectacular Stowe tradition.

Vermont Craft Beer

  Idletyme Brewing Company; Photo: Oliver Parini

Idletyme Brewing Company; Photo: Oliver Parini

History meets present day at Idletyme Brewing Company, a European-inspired brewery housed in an 1830s building that has previously been home to a cider mill, a camp run by a local legend, and a classic Stowe restaurant. Today, Brewmaster Will Gilson crafts creative flavor profiles that are a combination of classic European brewing and Vermont hop culture. The result: renowned brews like the Idletyme Double IPA.

Along with an incredible selection of ales and lagers (try the English Brown Ale, Danube Blueberry Hefeweizen, and Munich-style Helles Brook Lager), Idletyme also serves some of the best comfort food in Stowe from the casual Pub Burger to Truffle Mac-N-Cheese and Maine Crab Cakes.

A Fresh Take on New England Cuisine



In the realm of acclaimed restaurants, Plate stands out in both incredible cuisine and architectural design. The Main Street eatery was featured in Spain’s Voyeur Design magazine and the Restaurant & Bar Design Awards for its contemporary take on a rustic space – the work of designer and interior architect Tania Kratt.

On the menu, guests will find a combination of local flavors and healthy California style in dishes like the Beef Tenderloin with apple bacon maple bourbon chutney and the Roasted Southwestern Cauliflower with jalapeno lime quinoa and roasted red pepper coulis. There are plenty of vegan and gluten-free options, and you can even reserve the Chef’s Counter for up to four people for an up-close-and-personal view of the kitchen during your dining experience.

The Stowe Winter Carnival

For more than 40 years, the Stowe Winter Carnival has highlighted reasons why locals and visitors alike love Stowe. With 20 plus activities and events, the annual, two-week gathering brings the community together for winter sports, ice carving competitions, a children’s carnival, music, the infamous Snowgolf and Snowvolleyball tournaments, rail jams, and more.

During this year’s festival, held January 14 – 28, the theme will be “StowOasis.” The impressive NICA sanctioned Ice Carving Competition will take place on January 21, and for the second year, the Broomball Tournament and Beer Garden will be returning on January 27.

Snowshoeing Stowe Pinnacle

Much of the region’s beauty is visible from the ski slopes, but there are some views that require snowshoes and a short trek. At 2,651 feet, the summit of Stowe Pinnacle affords sweeping panoramas of the country to the west and the surrounding snow-covered forest.

Pack some French onion soup from the village or a mug of hot cider and begin your journey at the Upper Hollow Road parking area. The moderate trail winds through an open meadow and the forest, climbing 1,520 feet to a rocky overlook. Along the way, you may see animal tracks in the snow, perhaps even a wild turkey, and at the peak, unforgettable views over the Stowe countryside.