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

On Two Islands, Two Iconic Photographers

On Two Islands, Two Iconic Photographers

When she has a morning or afternoon free to point her camera anywhere at all, Cary Hazlegrove checks the tide charts and heads to Little Neck at dead low. Twice every day, that breezy western stretch of Nantucket island offers up seascape magnificence of one texture or another.

“Every low tide there is amazing,” says Hazlegrove, who arrived on the island 40 years ago with her Canon FTb manual-focus and no notion of making a career in photography. All these decades and installations and coffee table books later, she would qualify as Nantucket’s photographer laureate, if there were such a thing. Raised in Roanoke, VA, where her father practiced law and her mother was (and still is) a painter-sculptor, Hazlegrove made her life and her work into a combined art form, putting down deep roots in a creative community of island dwellers.

Her colleague and friend on the neighboring outpost of Martha’s Vineyard, the estimable Alison Shaw, has earned a similar distinction on her own shores. Shaw, who also made her way to these isles off Cape Cod in the experimental days of the 1970s, even has her own commercial space. You can admire her fine-art photos of the Vineyard year-round at the Alison Shaw Gallery, which Shaw owns with Sue Dawson, her partner in life as well as in business. The gallery can be found in a converted firehouse tucked into a historic section of Oak Bluffs called the Arts District.

Ferry Martha's Vineyard docked at Oak Bluffs, by Alison Shaw

Ferry Martha's Vineyard docked at Oak Bluffs, by Alison Shaw

When Shaw took up residence in Martha’s Vineyard, she was already a photographer and already familiar with the terrain, having spent childhood summers exploring it. She went to work for the island’s weekly paper, the Vineyard Gazette, and shot her own stuff on the side. Her mother had been a professional photographer, back in the pre-digital days of film, and young Alison learned by her side — in the field and in the darkroom, too.

Unlike Hazlegrove, who takes pleasure in shooting portraits, weddings, and the island’s manorial homes, Shaw uses time away from gallery management for fine-art photography only. “I have wonderful clients who come back year after year — one of them owns about 60 of my pieces — and when they ask about family portraits it’s always a painful moment,” says Shaw. “I have to find a polite way to say no.”

One of her many departures from this practice involves wooden boat-building — the aesthetics of that craft being so reliably interesting. A 40-by-50 color print on canvas, titled, “Schooner, Gannon & Benjamin Boat Yard 2001,” attests to what she can do with this visual material. It’s in the Shaw catalogue priced at $3,625.

Bike riding in Codfish Park, by Cary Hazlegrove | NantucketStock

Bike riding in Codfish Park, by Cary Hazlegrove | NantucketStock

In a typical year, roaming the Vineyard in all conditions and at all hours, Shaw produces 20 to 25 new pieces that she can call gallery-worthy. To see a wide selection of Hazlegrove’s work you would be guided to installations like the one put up recently at the Sconset Cafe, a top-rated eatery and exhibit space on Nantucket's eastern edge.

Hazlegrove moonlights as a singer in a progressive bluegrass and folk band called 4EZ Payments, who do some of their most inspired picking at Cisco Brewers out on Bartlett Farm Road. Her husband, the musician and composer A.W. Bullington, writes scores for films, podcasts, and ads and also composes the soundtracks for his wife’s documentary-style productions, which are montages of still photographs, video segments, original music, and a voice track of island residents offering descriptive and narrative ruminations. She’s done a long series of these multi-media expressions, which are available as DVDs and iBooks.

Shaw’s other creative outlet is teaching. She co-teaches a six-month mentoring program on the Vineyard together with Dawson (who brings to the program her expertise in graphic design, writing, social media, website design, and marketing) and also conducts workshops on the island, as well as in Maine and across the sound on Cape Cod. “I get a lot of fulfillment being with people who are true photo enthusiasts,” Shaw says. "Teaching keeps me energized, and so does the change of place I get when I do it.”

Lagoon Pond, by Alison Shaw

Lagoon Pond, by Alison Shaw

Locales like an Outer Cape beach are not exactly exotic for Shaw, but they have the benefit of being elsewhere than Martha’s Vineyard. Living on a relatively small island and spending a lifetime shooting landscapes and seascapes, you end up looking through the viewfinder at a lot of scenery you’ve already photographed. “If I were living in a mainland environment,” Shaw says, “I would head off to the next town or the next city to find something that’s visually new to me. On an island you’re forced to dig deeper.”

The Vineyard’s long summer days are an idyll for the rest of us, but for someone who earns a living shooting exteriors, it means getting up at 3:30 am to make good use of the morning glow, then waiting forever for the interesting contrasts and shadows of late-day light.

“Weather is an inspiration,” says Shaw. “The bigger storms light a fire under me. They can make the world change before your eyes, and when they’re gone some of them will have left the landscape — dunes and beaches especially — amazingly different from what it was before.”

Brant Point Lighthouse, by Cary Hazlegrove | NantucketStock

Brant Point Lighthouse, by Cary Hazlegrove | NantucketStock

Well-remembered comments by New Englanders about man’s juxtaposition with nature include this musing on the part of Henry David Thoreau: “For many years I was a self-appointed inspector of snowstorms and rainstorms, and did my duty faithfully, though [I was] never paid.” Some hear ironic self-deprecation in Thoreau’s comment, others a sincere grievance. Asked about it, Hazlegrove says she has long admired that quotation from Walden though she doesn’t personally identify with it.

“He felt a responsibility for what he came across in his ramblings,” she says — and indeed the rest of the quote is about Thoreau’s labors to keep “woodland paths open” and “ravines bridged and passable at all seasons.” That would not be the Hazlegrove mindset. “I’m drawn to whatever it is nature chooses to do, with no thought of cleaning up after it,” she says. “I just want to appreciate it.”

There are wintertime stretches when these islands experience a storm, its aftermath, another storm, another aftermath, over and over. “Weather is entertainment out here,” says Hazlegrove, citing the visual drama of a Nor’easter barreling up the Seaboard, bound for Nantucket. “But if you look at my work you’ll probably notice I tend to shoot what’s peaceful.”

Oak Bluffs Jetty, by Alison Shaw

Oak Bluffs Jetty, by Alison Shaw

Art that’s peaceful can still challenge an audience’s discernment, every bit as much as something raucous or confrontational. Shaw studied painting at Smith College and earned an art history degree there. She observes that, “The painter and the photographer end up in the same place, it’s just that the photographer starts with reality and has to work away from it — that’s a subtractive process, versus the painter starting with a blank canvas and doing something additive.”

That observation dovetails well with a trenchant line from Susan Sontag’s modern philosophical treatise, On Photography. In it Sontag declares, “The painter constructs, the photographer discloses.”

It’s estimated that over a trillion digital photos are taken each year with smartphones, most of them so heedlessly executed they give point-and-shoot a bad name. For the artist with a camera, wandering woodland or dunes or shorefront — and bearing the weight of their lofty aesthetic standards — the pursuit is demanding, at times surely daunting. View by view, motif by motif, you frame up the surface of the world, aching to give it depth.


Tradewind Aviation offers up to 25 scheduled shuttle flights to Nantucket every day from late April through early December – as well as private charters. Shuttles to Martha’s Vineyard run Thursday through Monday from May through November, with up to 15 flights per day.


Featured Photo: Aerial view of Great Point Lighthouse, by Cary Hazlegrove | NantucketStock

An Escape to Block Island

An Escape to Block Island

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

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

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

Where to Stay

Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

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

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

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

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

Where to Eat

Photo: Winfield's Restaurant

Photo: Winfield's Restaurant

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

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

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

What to Do

Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

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

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

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

Photo: Block Island Tourism Council

Photo: Block Island Tourism Council

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

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

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

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


Featured Photo: Block Island Tourism Council