St. Barth Gears Up for Fifth Annual Gourmet Festival

St. Barth Gears Up for Fifth Annual Gourmet Festival

The countdown has begun for the Caribbean’s most anticipated foodie fête: the St. Barth Gourmet Festival. From November 1 – 4, St. Barth’s top establishments will host an array of gastronomy-focused events, which showcase the culinary excellence of France’s leading chefs alongside the ingenuity of local talent.

Hurricane Irma may have forced the cancellation of last year’s festival, but the island has since been rebuilding to prepare for the 2018 – 2019 season, which kicks off with this event. So along with the fabulous multi-course wine-paired dinners, cooking competitions, and seminars, expect hefty sides of top-tier hotel and restaurant re-openings. Here, everything you need to know about the St. Barth Gourmet Festival — from star-studded events to must-see chef battles to where to stay.

Marquee Chefs Headline the Dinners at the St. Barth Gourmet Festival

Photo: Michael Gramm

Photo: Michael Gramm

To be sure, St. Barth has its own roster of star chefs, but the St. Barth Gourmet Festival casts a spotlight on the global leaders of French gastronomy. Meaning France’s Michelin-starred elite descend upon the tropics come early November. 

Executive Chef Nicolas Sale of two-Michelin star restaurant La Table de L’Espadon at the Ritz Hotel in Paris leads the 2018 festival. He will be serving up delectable French cuisine at the newly renovated Le Barthélemy Hotel. Joining Sale for the weekend are other toques of Michelin-starred pedigree including Chef Cédric Béchade of La Table de l'Auberge Basque, who will be cooking at Tamarin, and Chef Édouard Loubet of Domaine de Capelongue, who will be cooking at Hotel Le Toiny. You can also find Chef Virginie Basselot at Hotel Christopher, Chef Pierre Augé at Nikki Beach, and Chef Serge Labrosse at Bonito.

Each will host three nights of ticketed dinners (the Friday, Saturday, and Sunday of the festival), during which patrons can enjoy a four-course menu or an eight-course menu. Reservations begin at 7 pm and can be made directly by contacting the hotel or restaurant host.

Daytime Events Are All About Competition

Photo: Michael Gramm

Photo: Michael Gramm

During the days, the aforementioned top chefs alongside other French greats serve as juries to a series of competitions across the island. Don’t miss the largest event, “Le Concours de Barman” at 10 pm on Friday, November 2 at 25 Quarter in Gustavia. It’s the ultimate battle of island mixology, with St. Barth bartenders going head to head in creating original cocktail recipes.

A new addition this year is the “Joyfood Challenge” at Nikki Beach Restaurant on Saturday, November 3 starting at 10 am. Five local (amateur) cooking teams prepare and present their bespoke interpretation of “joyful food.” Expect a combination of praise and harsh critiques from the personality-driven panel.

You’ll need to wake up early on Sunday, November 4 to watch the most anticipated competition of the festival, “Le Concours St-Barth Chefs Challenge.” From 8 to 10 am, rising talents are challenged to create a dish that embodies "the island of St. Barthelemy." This cookoff, like all the daytime contests, is free and open to the public.

Major Re-Openings Will Be Timed With the Festival 

Photo: Tourism Committee

Photo: Tourism Committee

While many of St. Barth’s premier villas proved a quick fix after Hurricane Irma, it has been a different story for the island’s hotels. Yet thirteen months later, significant progress has been made – with favorites like Manapany and Villa Marie having opened earlier this year – and this fall we can look forward to a few major re-debuts in time for the St. Barth Gourmet Festival.

Le Toiny reopens on October 15 bigger and better than ever; check out the new hillside Villa Suites and beachfront pool in between festival events. If you’re looking for a quiet escape on the island’s north shore, Hotel Christopher rejoins the luxury space on October 17 after renovating more than 70 percent of its structures. And for a completely personalized stay, check into Le Barthélemy (which had just debuted months before Irma) for upgraded rooms and custom amenities like a pillow menu. The resort on Grand Cul de Sac will be back in action by October 28.

Featured Photo: Michael Gramm

The Return of St. Barth’s Luxury Hotels

The Return of St. Barth’s Luxury Hotels

In the year since Hurricane Irma struck St. Barth, the island has made an extraordinary recovery. 

Beaches and hillsides once covered in debris now flourish amid restoration programs and the addition of more than 1,500 new trees and plants. Gustavia’s restaurants and shops were revitalized and reopened soon after the storm. And as St. Barth prepares to welcome visitors back for the high season, some of the island’s top hotels are ready to make their long-awaited debut.

Joining Manapany on Anse des Cayes bay and Villa Marie in the hills above Colombier (both of which opened earlier in the year after renovations), here are the hotels returning to St. Barth this season. All are easily accessible when you fly to the island on Tradewind’s scheduled and private flights.

Hotel Christopher

Reopening October 17

Photo: Piter Juin

Photo: Piter Juin

Nestled along the northern coast of St. Barth, between the azure sea and Pointe Milou, Hotel Christopher is known for its intimate setting that feels both timeless and elegant.

With 70 percent of the hotel damaged during the storm – including the destruction of the beachfront restaurant – the team has spent the year renovating all 42 rooms and suites, updating Spa Sisley with a new fitness room and equipment, and relining the oceanfront infinity pool with eye-catching mosaics. Upon opening in the fall, revamped restaurants Taïno Lounge and Mango Beach Club will introduce new menus under the direction of Chef Nicolas Tissier.

Le Barthélemy Hotel

Reopening October 28

Photo: Laurent Benoit

Photo: Laurent Benoit

Blending Parisian style with the laidback setting of St. Barth, Le Barthélemy Hotel is the newest luxury retreat on the island – having opened in 2016 on a pristine stretch of Grand Cul de Sac.

The bespoke hideaway has upgraded all accommodations since the storm (including the addition of a pillow menu for customized rest, signature scents, and distinct lighting options) and added new two- and three-bedroom beachfront suites. A late-night rooftop bar will offer live music and DJs on weekends, while the renowned Aux Amis plans to expand beyond the restaurant and onto the beach for lunch. Make sure to also check out the expanded Le Spa, where you can enjoy new hot and cold baths, a sauna, hammam, and a tea salon.

Cheval Blanc

Reopening Early December

Photo: Mango PR

Photo: Mango PR

On the edge of Flamands Bay, Cheval Blanc will once again invite you into a lush garden with spectacular views of the Caribbean Sea. Inspired by the rhythm of island life, French designer Jacques Grange is leading the incredible redesign, orchestrating colors and textures in perfect vivid harmony to restore the Maison and hillside bungalows.

Thirty-four rooms, four one-bedroom suites, and two beachfront villas bathed in sunlight will debut for a soft opening in December alongside the revitalized Cheval Blanc Spa, The White Bar, La Canane de l’Isle, and the signature al fresco La Case de l’Isle by Chef Yann Vinsot.

Hotel Le Toiny

Reopening October 15

Tucked among the trees on a verdant hillside in Côte Sauvage, Hotel Le Toiny affords stunning vistas of the water below. The private and exclusive resort reopens next month with enhanced facilities and eight all-new suites designed by the acclaimed Bee Osborn.

Known for her residential designs in the United Kingdom and beyond, Osborn draws inspiration from classic interiors while infusing her work with modern energy and dynamic lighting. Her latest creations at Le Toiny include seven one-bedroom suites and a two-bedroom suite, each with a private terrace, ocean-view pool, and lush landscaping designed to offer guests a sense of quiet seclusion.

Le Sereno

Reopening December 1 

Photo: Sereno Hotels

Photo: Sereno Hotels

Simplicity meets style at Le Sereno, an intimate beachfront resort on Grand Cul de Sac that spans 600 feet of pristine white sand. When the property reopens this winter, guests can expect an innovative new restaurant, completely redesigned rooms including new family suites with private pools, a new fitness facility, and an enhanced spa. Although most of the hotel will be new as a result of the storm, the spirit of Le Sereno – like the island – will remain the same.

Featured Photo: Sereno Hotels

Sailing Antigua: 7 Days in the West Indies

Sailing Antigua: 7 Days in the West Indies

Home to some of the most spectacular sailing events in the Caribbean, from Antigua Sailing Week to the Antigua Classic Yacht Regatta, Antigua brims with white-sand beaches and deserted coves straight from your sailing daydreams. Blending natural splendor and centuries-old sailing culture, the island is a must-see for experienced sailors and first-timers alike.

Below, a one-week sailing itinerary highlighting some of the island’s most sought-after stopping-off points. After landing on the northern coast with Tradewind Aviation, your first destination is one of Antigua’s most famous.

Day 1: English Harbor

Photo: Stephen Davies

Photo: Stephen Davies

Framed by towering fortresses and sweeping beaches, English Harbour exudes naval history as the founding place for the Royal Navy’s Caribbean fleet in the eighteenth century. A day in the harbor puts you close to fascinating outposts like the restored marina Nelson’s Dockyard and the restored military lookout Shirley Heights, a UNESCO World Heritage Site.

Step inside Admiral’s House Museum – also in Nelson’s Dockyard National Park – to learn about the importance of the dockyard in Antiguan and Caribbean history, then climb up to Shirley Heights Lookout for one of the most iconic images of Antigua: English Harbour and Falmouth Harbour at sunset. The former military base has been converted into a restaurant and bar and is the perfect place to end the day on Sundays with an evening party and live steel drum band.

Day 2: Nonsuch Bay

Photo : Andrew Moore via Flickr / CC BY

Photo: Andrew Moore via Flickr / CC BY

Your first day on the open water takes you to Nonsuch Bay, about eight miles northeast of English Harbour. On the way, you will pass Half Moon Bay Beach, one of Antigua’s most beautiful shorelines and snorkeling destinations, and York Island, which should be given a wide berth when sailing. Protected by a windward barrier reef, the secluded Nonsuch Bay is the perfect place to anchor for the night.

Near the edge of the bay, the uninhabited Green Island is a favorite among sailors who frequent Antigua with its tranquil white-sand beaches, lush greenery, and variety of exotic birds onshore.

Day 3: Great Bird Island

Photo: Charles J. Sharp via Wikimedia Commons

Photo: Charles J. Sharp via Wikimedia Commons

Quiet and serene, Great Bird Island off of Antigua’s northeastern coast is both a spectacular beach escape and a 20-acre sanctuary for endangered wildlife like red-billed tropicbirds, West Indian whistling ducks, frigates, and rare lizards.

As you sail from Nonsuch Bay to the island, you will spot Devil’s Bridge – a natural arch carved by the sea – and Mercer’s Creek Bay, home to Stingray City Antigua, along your route. Once anchored, explore the destination’s vibrant coral reefs and take a hike to the top of the island for exceptional views of the surrounding North Sound National Park.

Day 4: Dickenson Bay

One of the most beautiful and popular locales on the island, the white-sand beaches of Dickenson Bay are home to many of Antigua’s high-end resorts, along with restaurants, shops, and adventure activities. Pass Prickly Pear Island and Jumby Bay Resort on Long Island to reach the lively enclave, then spend your time soaking up local culture, windsurfing, and horseback riding on sugary white-sand beaches.

Overlooking the picturesque shoreline, casual elegant eateries like Ana’s Restaurant and Art Gallery and Coconut Grove beckon, and just outside of the bay, there are a few uninhabited islands that are worth a snorkeling trip for their one-mile-long coral reef brimming with diverse marine life.

Day 5: Deep Bay

Not far from Dickenson Bay, take a short sail past Fort James and St. Johns (the capital of Antigua) to anchor in Deep Bay. With protected waters and a hundred-year-old shipwreck in the middle of the bay, the destination is ideal for snorkeling. Onshore, pristine beaches are the perfect place to sunbathe – but offer little shade – and interesting hikes abound in the surrounding landscape. Walk to the tip of the cape to take in the boundless ocean at sunset, and hike ten minutes north to the hilltop Fort Barrington to go back more than 200 years in history and enjoy sweeping vistas of the island.

Day 6: Jolly Harbour

Photo: David Stanley via Wikimedia Commons

Photo: David Stanley via Wikimedia Commons

One of Antigua’s most well-known destinations, Jolly Harbour welcomes sailors to a bustling marina, a one-mile long shoreline that is perhaps the widest on the island, and some of the island’s best restaurants. After sailing past Five Islands and reaching the marina, spend your day indulging in freshly caught lobster and coconut shrimp at outposts like The Nest Beach Bar and Restaurant (on the neighboring Valley Church Beach) and swimming in the shallow waters of Jolly Beach, or plan for an afternoon at The Jolly Harbour Golf Club, an 18-hole championship course.

Day 7: Falmouth Harbour

Photo: Falmouth Harbour Marina

Photo: Falmouth Harbour Marina

Complete your journey close to where you began in Falmouth Harbour, a horseshoe-shaped bay on the southern coast featuring three expansive marinas and a boatyard. The hub for Antigua’s yachting community can be reached by passing Cades Reef – where snorkeling the inner reef may bring you face to face with stingrays and harmless reef sharks – and Carlisle Bay Antigua. Once docked alongside Antigua’s luxury yachts in the harbor, take a dive in the bay to explore the iconic Pillars of Hercules underwater. If you need to head back to the neighboring English Harbour to wrap up your trip, simply head around the point.

Eyes on the Sky: A Pilot’s Account of Flying for Tradewind

Eyes on the Sky: A Pilot’s Account of Flying for Tradewind

Omar Webber discovered his passion at the age of three: Rising just after the Jamaican sun each day, he would step outside, look up to the sky, and watch his dad zip by in a Cessna 172 Skyhawk en route to local fields for crop dusting.

“Every time he went flying I said I wanted to go with him,” says Webber, whose father finally relented. “He gave me the controls and I had fallen in love. That’s what I wanted to be.”

For those drawn to aviation, no feeling compares to soaring thousands of feet above the ground, and for pilots with a passion for safely and efficiently navigating the Northeast, Caribbean, and beyond, Tradewind Aviation may offer the type of flying they’ve always dreamed of.


After completing his licenses through a flight school in Farmingdale, New York, Webber met a mechanic based out of Oxford, Connecticut — the location of Tradewind’s headquarters — who told him about the company’s opportunities for pilots. Webber had originally intended to fly for smaller airlines before moving on to commercial, but after becoming immersed in the Tradewind lifestyle, he decided he had found somewhere special.

“It felt like a family atmosphere, and the culture was good,” he says. “Everyone helped each other and was friendly, and I always felt like they had my back if anything should happen. The work environment is pretty healthy.”

The interesting routes, too, kept Webber coming back rotation after rotation, like the ones from San Juan to the exclusive island of St. Barth — which looks different depending on your approach and requires peak performance to complete the landing on a 650-meter runway bookended between ocean and mountain.

“One of my favorite experiences working with Tradewind Aviation has been landing on St. Barth, mainly because of the challenges,” says Webber, noting that he became a better pilot in maneuvering landing strips made for smaller planes like the Pilatus PC-12. “If I ever flew commercial, it would be a piece of cake. Flying into JFK or La Guardia would be very easy – a walk in the park.”


Soon after his arrival, it became clear to Webber that fellow Tradewind employees — from pilots to scheduling specialists to maintenance crews — were always operating on the top of their game. He immediately got to work too, reflecting the standard operating procedure that was pervasive throughout the company.

“The training department does a great job,” he says. “When everyone’s on the same page, you’re not spoon-feeding anyone. There’s a baseline to everything, so everyone knows what needs to be done and how to get it done.”

Tradewind management noticed Webber’s enthusiasm as well, and within nine months, he was promoted from first officer to captain. He explains, “Pilots have the opportunity to build time fast. There is room to grow here.”

Wrapping up his second year of flying for the company, Webber has grown quite comfortable with the lifestyle. Depending on the weather and how many scheduled legs exist on a given day, he explains that an average shuttle rotation lasts nine to 10 hours and could involve three round trips from White Plains to Nantucket and back. When not shuttling, Webber and crew are running charter trips to deliver passengers to coveted destinations throughout New England and the Caribbean.


“It’s not really set in stone,” he says. “I like the variety. If you need a change of scenery, you just make a phone call, and if they can, they’ll move you to do some charters.”

Due to the family-like culture that has been well established at Tradewind, Webber says there is opportunity for internal flexibility from management that understands, and appreciates, that employees have lives outside of work.

“If I need a day off or I need something done at a certain time, I can tell them my plans and no one ignores my requests,” he says, recalling the optionality granted to him when his wife was pregnant. “Their operations are well planned, so me leaving does not affect them. I’ve worked many jobs, and I feel like Tradewind cares more about me and my family.”

For new pilots interested in flying for Tradewind, Webber suggests asking a lot of questions, being prepared to be a team player, and listening to advice.

“Tradewind is one of the best operators out there for people coming up in aviation,” he says. “We do it well, and do it safely.”


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

Off the Beaten Path: 9 Nature Gems in the Caribbean

Off the Beaten Path: 9 Nature Gems in the Caribbean

With more than 7,000 islands, islets, and cays, the Caribbean attracts sightseers and adventurers from every corner of the world. Besides the region’s ubiquity of clear waters and exquisite white sands that are unanimously favored by visitors, there are a few lesser-known treasures awaiting exploration.

To make the most out of a stay on the Leeward Islands, we put together a list of essential destinations for a one-of-a-kind trip. Best of all, these Caribbean jewels lie in wait only a short flight away on one of Tradewind’s world-class Pilatus PC-12s or Citation CJ3s.

Colombier Beach, St. Barth

A sunset at Colombier Beach in St. Barth

To get a slice of personal paradise, sometimes you have to head off the beaten path. Luckily, accessing the exclusive Colombier Beach only requires a scenic 20-minute hike or a 10-minute boat ride from Gustavia Harbor into the bay. Considered by many locals and vacationers to be the finest stretch of beach on St. Barth, Colombier is a haven for starfish, sea turtles, coral, and various schools of vibrant fish — all of which can be intimately experienced with the aid of a snorkel.

As visitors are drawn to more convenient, amenity-driven beaches on the island, those who make the trek will discover an almost untouched playground of white sand and clear blue water, ideal for swimming or floating under the Caribbean sun. Because there are no amenities, however, guests should bring their own picnic for the day (ask your hotel to prepare a bag or stop by Maya’s To Go).

Little Bay, Anguilla

Photo: Anguilla Tourist Board

Photo: Anguilla Tourist Board

While Anguilla is acclaimed for its picturesque, uncrowded beaches, there’s one in particular offering even more seclusion and serenity. Only accessible by boat or kayak through Crocus Bay, or by descending down a steep bluff, Little Bay is the most protected and remote beach on the island.

This distinct cove of azure water and small stretch of shore provides an ideal refuge for a day of swimming, snorkeling, and lounging on the sand. Swim to the northeast side of the bay to scale and jump from a massive rock jutting out of the sea. Known to residents simply as “The Rock,” the boulder seems like it’s all but hovering over the bright blue surface of the water. Because the hidden inlet is so exclusive, visitors may only be sharing it with pods of local pelicans.

Devil’s Bridge, Antigua

Photo : z_Dead via Flickr / CC BY

Photo: z_Dead via Flickr / CC BY

The product of countless years of ocean erosion, this rocky arch forms a natural bridge over the tides of Antigua’s northeast coast. As waves crash against its riddled surface, seawater blasts through limestone blowholes in hundreds of piping geysers.

Located in Indian Town — an Antigua national park and historical site where Amerindian artifacts have been excavated — Devil’s Bridge may have been home to some of the island’s earliest residents.

Botanical Gardens, Nevis

Photo : David Broad via Wikimedia Commons / CC BY

Photo: David Broad via Wikimedia Commons / CC BY

Just beyond the twin statues of Cambodian dragons that flank the gate to the Nevis Botanical Gardens lies a tranquil oasis of stunning and delicate flora hailing from all over the world. Wrapped around the ruins of a lost temple, this five-acre rainforest conservatory features waterfalls, lily ponds, a bamboo grove, a tropical fruit garden, over 100 species of palms, and a vibrant orchid collection that’s recognized as one of the largest in the Caribbean.

A wondrous array of tropical color isn’t the only exotic allure inside the garden grounds. Thoughtfully dispersed through its lush, winding pathways are scores of sculptures and artifacts, including a replica of a pre-Columbian Olmec head and a Ganesh statue from India. In the heart of this verdant enclave, complete with flitting purple hummingbirds and talkative African green parrots, sits Oasis in the Gardens — a restaurant serving world-renowned Thai cuisine and offering striking veranda views of Nevis Peak, Charlestown, and St. Kitts.

Friar’s Bay, St. Kitts

Photo : Fred Hsu via Wikimedia Commons / CC BY

Photo: Fred Hsu via Wikimedia Commons / CC BY

After a short, two-mile ferry ride from Nevis across “The Narrows,” you’ll find the volcanic island of St. Kitts. With an economy dependent on the exportation of sugar cane up until 2005, the island is relatively new to the tourist industry. What this means for visitors, at least for the time being, is that St. Kitts remains a unique enclave replete with authentic and unfettered local Caribbean culture. 

As St. Kitts tapers off into a thin peninsula on its southern end, a stark duality can be observed at Friar’s Bay where the Atlantic Ocean meets the Caribbean Sea. Just a thin strip of land separates the sprawling, choppy Atlantic from the calmer Caribbean, and observing the contrast of the two bodies of water is spectacular on its own. Add to that the choice of two pristine beaches and some of the island’s best snorkeling opportunities, and you’ll be hopping back and forth to savor the unique characteristics of each.

Fountain Cavern National Park, Anguilla

Photo: Anguilla National Trust

Photo: Anguilla National Trust

For a taste of what life may have been like for natives who originally inhabited Anguilla, pay a visit to Fountain Cavern National Park, a protected archeology site and treasured testament to the history and culture of the Amerindian Taino people. The focal point of the park, set back in a cave 70 feet above the sea, is the Fountain itself. Long used as a local source for reliably clean water, it continuously pumps a fresh stream into Shoal Bay from 50 feet below Anguilla.

Once a place of supernatural worship, the Fountain is the oldest ceremonial cave site in the Caribbean — and through archeological studies of the various glyphs and rock carvings spanning 1,000 years, it’s also deemed as the longest used. Hanging from the massive domed limestone cavern is a 16-foot stalagmite where natives carved the head of Jocahu, the Taino spirit of fertility. Believing that the sun, the moon, and the first people emerged from caves, Caribbean Amerindians used the cavern and its vast, interconnected network of underground grottos to honor the deities in their pantheon and ward off evil spirits.

Anse de Grand Fond, St. Barth

An image of the rocky shoreline at Anse de Grand Fond

Tucked into a bay on the southeast side of the island is Anse de Grand Frond — otherwise known as the “wild coast” — a rugged beach where you can find natural landmarks as mysterious as they are beautiful. Here, where surging ocean meets coral rocks, visitors can hike the shoreline to discover the Washing Machine, a series a small pools roiling in rhythmic, hypnotizing whirls as they are continually filtered by the churning tide.

Further along the rocky path, complete with nomadic goats, bathe in the Natural Pools, sun-warmed pockets of bright green water that have been deposited by the surf.

Nevis Peak, Nevis

Photo : David Broad via Wikimedia Commons / CC BY

Photo: David Broad via Wikimedia Commons / CC BY

The prominent feature of St. Kitts’ sister island, looming 3,230 feet above its sandy shores, is Nevis Peak. Although the volcano has been dormant throughout recorded history, its lush coastal slopes still vent hot sulfurous gases through various springs and fumaroles.

Summiting the highest point in Nevis via guided trek is not an easy feat, but if the clouds cooperate, the peak rewards hikers with sweeping views of the Atlantic Ocean and Caribbean Sea, plus a panoramic vantage of the Leeward Island chain.

Situated among the tropical gardens on the south side of the volcano is The Hermitage Plantation Inn, a colonial-style boutique assembled from vintage cottages originating around the island. Built around a house originally erected in 1670 (thought to be the oldest standing wooden structure in all the Caribbean), this charming hotel and its meandering grounds afford visitors the opportunity to soak up an authentic dose of island life from the comfort of a veranda or hammock while listening to conversations of green vervet monkeys as they play in the trees.

Buck Island, St. Croix

Whether it’s the impeccable soft sands of Turtle Beach or the marine garden wonderland of the Buck Island Reef National Monument, a day full of breathtaking surprises awaits just one and a half miles off the north coast of St. Croix.

Because two-thirds of Buck Island is surrounded by a 7,000-year-old elkhorn coral barrier reef, the monument area provides some of the best snorkeling in all of the Leeward Islands. In addition to exploring 704 acres of marine habitat filled with over 250 species of varicolored fish, snorkelers can navigate a subaquatic trail (one of only three in the US) to discover an ecosystem teeming with sea life like barracuda, parrot fish, squid, and vibrant brain coral. When they come ashore, visitors enjoy hiking over the crest of the hill to take in spectacular sea views and to try their luck in spotting brown pelicans, least terns, and sea turtles — all endangered species that have made their homes on the protected island.


Featured Photo: Anguilla Tourist Board

An Insider’s Guide to Dog-Friendly Martha’s Vineyard

An Insider’s Guide to Dog-Friendly Martha’s Vineyard

Four-legged family members are always welcome on Tradewind Aviation flights, but as every dog owner knows, hotels, restaurants, beaches, and stores aren’t always as accommodating. Here, find out how you can have the ultimate stay on Martha’s Vineyard and never have to leave Fido behind.

Where to Stay

Photo: Harbor View Hotel

Photo: Harbor View Hotel

It’s a dog’s world, and we’re simply living in it at Harbor View Hotel in Edgartown. Canine guests are showered with amenities through the Island Dog Package — treats and toys by famed island retailer The Black Dog greet upon arrival (plus, mom and dad get a Vineyard Seadogs calendar.)

Pooches love the residential-style Captain’s Cottages, where a living and dining room, kitchenette, separate master bedroom, and expansive balcony offer plenty of space for discovery, indoor fetch, and cuddles.

Canine guests can also laze days away on The Great Lawn, a spacious and grassy social spot at the property’s core, or chill on the wrap-around porch of the principal 1891 historic building while human companions enjoy a good read — or simply the view — from one of the many ocean-facing rocking chairs.

Where to Eat

Photo: Alchemy

Photo: Alchemy

Begin your days at Espresso Love. Strong lattes and fresh-baked croissants (especially the almond variety) go well with mornings of doggie socializing — the patio here is equally popular with humans and canines in the morning. The café also serves light fare throughout the day.

Alternatively, hang out on the al fresco terrace of Behind the Bookstore, a pet-friendly coffee shop and bistro directly behind Edgartown Books. In the morning, opt for a “Café Shakerato,” a frothy coffee drink with orange bitters, or an iced mint latte complemented by a sandwich from the “bagel bar.” Past noon, try the poached local scallop bowl over spring pea puree, washed down with an artisanal cocktail like the “Eazy Breezy,” a refreshing mix of hibiscus vodka, lime, elderflower, ginger, and sparkling wine.

For dinner, book a table on the patio at Alchemy, an Edgartown institution that just revamped the menu and wine program on the eve of its 20th anniversary. Though Fido won’t be able to appreciate the elevated wine list (curated by noted wine advisor Jamie McNeely) or the award-winning cocktail list (recipient of “Best Cocktails on the Island” by Martha’s Vineyard magazine), he’ll likely learn new tricks for a bit of leftovers. Expect lots of tail wagging after scraps of the Pan Seared Striped Bass, the Crispy Roasted Half Chicken, or the filet of Beef Tenderloin.

Where to Shop

Retail therapy isn’t just for humans on Martha’s Vineyard. Dogs can shop for fashionable leashes, raincoats, bowls, mugs, and other trinkets and toys at Good Dog Goods in Oak Bluffs. However, the highlight of any visit here is a treat from the doggie bakery, which sells delectable — and adorable — cookies fashioned after lobsters, whales, and lighthouses.

Dogs are also welcomed at all outposts of The Black Dog stores across the island. This iconic retailer, which hails from Martha’s Vineyard, is known nationally for its black-emblazoned merchandise and has stores in Edgartown, Oak Bluffs, and Vineyard Haven as well as a circa 1971 tavern in Vineyard Haven, where dogs are welcomed outdoors.

Where to Play

A dog plays on a beach in Martha's Vineyard

You’ll need a PhD in beach rules and regulations to know which Vineyard swathes you can stroll with your dog (read: the best thing to do is to consult the concierge at the Harbor View Hotel and pay attention to the beach signs).

At Eastville Point Beach and Norton Point Beach, for example, dogs can roam free outside of tourist season and nesting season (September 15 to March 31.) From April 1 to August 30, dogs are prohibited within 100 yards of a posted nesting habitat, and from May 15 to September 15, dogs are prohibited on the beach between 9 am and 5 pm. So, it’s still entirely possible to enjoy a morning sunrise walk or early evening sunset walk down from Fuller Street Beach (right behind the Harbor View Hotel) to Edgartown Lighthouse Beach, anytime of the year.

For outdoor summertime fun without limits, head to the 72-acre Trade Wind Fields Preserve in Oak Bluffs where dogs can enjoy forested walking trails leash-free – and likely make a few new friends along the way. Alternatively, take the Chappy ferry to Cape Poge Wildlife Refuge, underscored by seven miles of barrier beach and a grove of hundred-year-old red cedars. Year-round, dogs are allowed throughout the refuge as long as they remain on-leash.


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.


Featured Photo: Harbor View Hotel