Six Towns, One Island: Your Guide to Martha’s Vineyard

Six Towns, One Island: Your Guide to Martha’s Vineyard

Coastal charm abounds from shore to shore on the storied island of Martha’s Vineyard. But among great expanses of beach, forest, and countryside, six seaside villages each offer their own personality and historic splendor.

The bustling villages on the eastern side of the island, or down-Island, will be most familiar to visitors, from beautiful Edgartown to Oak Bluffs to Vineyard Haven. And to the west, or up-Island, the remote villages of Aquinnah, Chilmark, and West Tisbury entice with quaint towns and rolling hillsides. (The directions hail from whaling days – when seamen heading “up” traveled west, seeing increasing numbers of longitude, while those heading “down” traveled east back to England.)

To truly explore each village, you would need more than a day, and with Tradewind Aviation’s regularly scheduled shuttles to Martha’s Vineyard and private charters, an easy getaway is always at your fingertips.

Below is a general overview of each destination, complete with recommendations for dining:


Photo: Barry Peters

Photo: Barry Peters

With a picturesque port that regularly hosts yachts and sailing regattas, Edgartown is one of New England’s most sought-after coastal retreats. The elegant village in the southeast is home to a flourishing town center, grand churches built during the whaling era, the white-painted captains’ houses, and miles of scenic beaches accented by Edgartown Lighthouse. It is one of only two “wet” towns on the island, making for lively nightlife in the summer.

Must-try Restaurant: Atria, a polished local eatery with global inspiration and an ever-evolving menu. Try the Pay Day burger with black truffle aioli, arugula, forest mushrooms, red wine reduction, and seared foie gras.


Dramatic coastlines and sweeping hillsides define Chilmark, home to some of the best sunset views on the entire island. Along with lovely nature preserves, you can find pastures of grazing sheep, the rocky northern shore offering vistas of the Elizabeth Islands, and the charming fishing town of Menemsha with its little shops and fresh seafood restaurants. The village also encompasses the island of Noman’s Land, a federal bird sanctuary closed to visitors.

Must-try Restaurant: Larsen’s Fish Market, a quaint market-slash-restaurant located on the fishing docks of Menemsha. Try the littleneck and cherrystone clams.

Oak Bluffs

Photo: Michele Schaffer

Photo: Michele Schaffer

Modern elegance meets rich history in Oak Bluffs, a lively harbor-side village extending inland from East Chop Light. A walk through town will take you to the multi-colored gingerbread cottages, displaying their whimsical, Victorian architecture, as well as the open-air Tabernacle, Union Chapel, and the oldest platform carousel in the nation. Great expanses of pristine beaches are the village’s main draw, and in the evenings, visitors can enjoy vibrant nightlife and late-night pastries at Back Door Donuts.

Must-try Restaurant: Red Cat Kitchen, a tucked-away eatery with bold, artistic presentations and a nightly-changing menu.

Vineyard Haven

A place for the arts, Vineyard Haven brims with galleries and free musical performances. A walk down Main Street will take you by the renowned Bunch of Grapes bookstore, exquisite shopping and dining, and just a block away, the Vineyard Playhouse. The village was once one of the busiest shipping ports on the East Coast and today remains the island’s main port of entry. It is also very interchangeably referred to as Tisbury.

Must-try Restaurant: Little House Café, an intimate establishment with a menu brimming with creative flavor. Try the fish tacos.


Gay Head Cliffs in Aquinnah, Martha's Vineyard

Located at the westernmost point of Martha’s Vineyard, Aquinnah is home to the stunning Gay Head Cliffs (formed from colorful clay deposits) with Gay Head Lighthouse standing atop them. The village itself is less than six square miles and offers a tranquil way of life in the country. It also harbors the lands of the Wampanoag Native American Tribe of Gay Head.

Must-try Restaurant: Aquinnah Shop Restaurant, a vibrant oceanfront destination with expansive decks and both American and Native American dishes. Try the Codzolez codfish cakes topped with pico de gallo and guacamole.

West Tisbury

Not to be confused with Vineyard Haven, West Tisbury is a destination in itself. The idyllic village abounds with rural charm, highlighting a 4,000-acre state forest and the grounds of the annual Martha’s Vineyard Agricultural Society fair. In the small downtown center, you can find the historic Alley’s General Store catty-corner from the Field Gallery (you will know it by the dancing lawn sculptures), and for another bit of history, head down the street to Grange Hall.

Must-try Restaurant: Scottish Bakehouse, a health-conscious bakery serving everything from quinoa burgers to coconut tofu. Try the famous egg sandwich.

Chip Webster, The Guardian of Nantucket Architecture

Chip Webster, The Guardian of Nantucket Architecture

You could say that preserving traditional Nantucket architecture is in Chip Webster's blood.

Webster is the go-to architect if you want to build a home that fits into traditional Nantucket—given the island's strict architectural review guidelines, there is almost no other kind—and it's almost as if fate chose Webster for this role. His forebears were one of the five families that first settled the island some 300 years ago. He's done a lot of roaming around—travelled around the world, spent two years doing film and videos, restored a home in Cambridge—but he finally came home to roost in 1991 because he sensed that Nantucket was going to "catch the recovery wave." At the time, the country was experiencing a recession, but Webster says Nantucket is a leading indicator of the real estate market. 

"In 1991 the island started coming back really strong," he says, which prompted him to move his architectural practice to Nantucket from Cambridge.

Now he leads a double life: the man who knows how to do Nantucket traditional on Nantucket, and the man who travels to do innovative contemporary in places like Aspen, Colorado.

He was in charge of restoring one of Nantucket's prime landmarks, Greater Light, which was built in 1791 to house livestock and later became the 1920s home of Hanna and Gertrude Monaghan, prominent members of that decade's Nantucket artist colony. (The name was taken from Genesis 1:16; the sisters were very religious). The place was a wreck when he started the project, having been uninhabited for a decade. "It is a building that would be impossible to recreate today, given current regulations and requirements," Webster says.

Then there's the other side of his talent. "We do a lot of ski- and beach-vacation homes," he says. (For the record, he lives in a mixed-use building—home, office, and community spaces—just outside Nantucket town.)

But would-be Nantucketers come to Webster because knowing how to do traditional on Nantucket is more than being an architect.

"Working on Nantucket is arguably one of the most restrictive places on the planet," he says, referring to the island's Historic District Commission, established in 1955 to ensure that the island's downtown core would not turn into Malibu-like exercises in vanity architecture. 

This actually began to happen in Madaket in the '70s, architecture that Webster calls "triangular masses." The Board subsequently extended its purview to the entire island—"Even a lunch patio or a trim color has to be approved," says Webster—but he sees its worth. "The downtown core has one of the best collections of pre-Civil-War houses in the country," he says, in a tip of the hat.

"Usually the road to success in architecture is to create a very identifiable style," he says (and one thinks immediately of Gehry or Calatrava).

But Webster is a nuancier: Consistent doesn't have to mean homogeneous, he explains. And he has also become a bit of a Historic District Commission mind-reader. The Commission generally wants the same thing, but without tassels, a swag, or a new detail.

"Generally speaking," he says, “The Board is not looking for symmetry and balance. If you go in with the dead symmetrical house, you're going to have a hard time."

And you can sometimes over-game the situation. "It can backfire on you. You put in something a little bizarre thinking you'll take it out, but then they like it," he says. So he no longer puts up bargaining chips, and he admits that the Board's demands produce an interesting architectural vernacular within established boundaries that are appropriate to the island.

“Houses on Nantucket today are built to last 100 years and anthropologists will be able to date them exactly."


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

*All photos courtesy of Chip Webster Architecture

Private Aviation for Pets: When Dogs Fly Tradewind

Private Aviation for Pets: When Dogs Fly Tradewind

Be it the white-sand beaches of St. Barth or the cobblestoned streets of Nantucket, vacation travels are even more complete in the company of your furry best friend. Hence why Tradewind Aviation offers pet-friendly flights to the Northeast, Caribbean, and beyond, ensuring that no member of the family is ever left behind.

Pets of all sizes, including large-breed dogs, are welcome to fly in the spacious cabins of our Citation CJ3s and Pilatus PC-12s. (Note: Limit one party with pets per flight and seats must be purchased for dogs over 100 pounds.) Without the stress and discomfort of the cargo hold, four-legged passengers will arrive at your destination feeling relaxed and ready to enjoy their getaway.

In celebration of Pet Appreciation Week, below are some of our favorite moments over the last few years of pet-friendly travel. Bring your pup for your next vacation and be sure to tag us at @flytradewind to give him or her a share of the spotlight!

Contact our Reservations department for details or questions: [email protected] or 800-376-7922.

Left: @oliverofnyc Right: @ronda320

Cover photo courtesy of:  lindsayhelms / 123RF Stock Photo

The Quintessential Nantucket Retreat

The Quintessential Nantucket Retreat

As you approach The Wauwinet on Wauwinet Road, the land tapers as the bumptious ocean on the right meets the calm bay on the left. Think of a lobster tail, as it's one of the dishes for which the hotel is known. Things taper at the top and The Wauwinet is no exception: You're arriving at one of Nantucket's top luxury enclaves (the island's only Relais & Châteaux property).

The 33-room hotel and its four free-standing guest cottages occupy a cluster of 19th-century shingled buildings that face an unnamed private beach. Across the road—on the ocean side—is Great Point Beach, and just outside that is the Coskata-Coatue Wildlife Refuge (so bring your binoculars). People drive all this way—the 17-minute drive from the airport, where Tradewind flights touch down at the center of the island, is lengthy by Nantucket standards—to dine at TOPPER’S, the hotel's lauded-to-the-moon restaurant named for the owners' Welsh Terrier. (Ever had a Nantucket lobster, leek, and basil frittata for breakfast? Didn't think so.)


In hotel terms, The Wauwinet is a moon shot: a boutique hotel, on a short-season island, with the polish of New England and personality of Provence. Think: rooms with character (antique pine, wicker, and tasteful chintz reign), luxe accessories (Pratesi bed linen), excellent service, a 1,000-label wine list, that unnamed private beach, two clay tennis courts, and locally sourced seafood and produce at TOPPER’S just downstairs (lobster navarin for dinner).

When you're here, you've arrived, and in the best tradition of luxury boutique hotels, you may not want to go anywhere else. Which is one reason to taxi to the hotel from the airport and figure out the rest. (Guests who book the three-bedroom Anchorage House, a stand-alone bungalow, are offered a BMW gratis.)

Not that staying at The Wauwinet means you’re stranded. The hotel shuttle makes the nine-mile trip to and from Nantucket Town almost hourly in-season, and the hotel has a boat that offers a tour of the harbor—Captain Rob McMullen knows these waters like the back of his hand.  

The catch is that most of the rooms are small. Top-floor rooms have the best bay views, and if you're looking for a honeymoon feel, then book one of the four freestanding cottages (cozy gas fireplaces and sundecks). At the end of the day, though, there's an equalizer: that sunset over the bay on the hotel's private beach.  

The only rule?

Come as you are.


*All photos courtesy of The Wauwinet.

6 East Coast Golf Getaways That Prove Rankings Don't Mean Everything

6 East Coast Golf Getaways That Prove Rankings Don't Mean Everything

Written by David Gould, a former Executive Editor of Travel + Leisure Golf who has authored several books on golf history and course architecture.


One evening I stood in a tavern among a group of well-traveled golf writers, talking shop. An avid golfer who had joined the conversation floated a query: After all the years and all the trips, which course is your favorite? He seemed puzzled by the answers, likely because “favorite” wasn’t taken to be synonymous with “famous” or “award-winning.” Instead we each named a very fine course we had developed a fondness for, where we’d met great people and enjoyed experiences we wouldn’t ever forget.

Golfers who aren’t fixated on rankings and ratings can develop an instinct for golf destinations that will suit their fancy. There’s nothing wrong with prestige and awards—you just don’t want to be a slave to them. What works best is when you have a hunch you’re going to love a certain golf experience, then you set off and discover your intuition was spot-on.

This collection of a half-dozen courses along the Eastern Seaboard—each worthy of a chartered golf getaway with Tradewind Aviation—does contain greatness. Yet it’s mainly a sixth-sense kind of list, blending elements of architecture, setting, scenery, and some kind of spirit that holds it all together.

Photo: Courtesy of Cabot Links / Evan Schiller

Photo: Courtesy of Cabot Links / Evan Schiller

Cabot Cliffs, Inverness, Nova Scotia, Canada: We’re not breaking the intuition rule by including Cabot Cliffs, despite all the acclaim it’s received since coming online two years ago. That’s because the Canadian Maritimes are physically remote and their character is unassuming—you have to feel drawn there. Of course, having a chartered private jet fixes the remote part, delivering you to a jaw-dropping golf landscape overlaid with the strategic subtleties its designers, Bill Coore and Ben Crenshaw, specialize in. They built one hole—the cliff-to-cliff par-3 No. 16—that no golfer has ever played without first photographing it. If you take this trip there is one place to stay, the Cabot Links Lodge—well-designed, comfortable, and just right for its time and place. Time your Nova Scotia getaway for midsummer and you can see classic MGs, Austin Healys, and Triumph TR6s, plus vintage motorcycles, at the Eighth Annual British Motoring Festival, July 14-16.

Photo: Nemacolin Woodlands Resort

Photo: Nemacolin Woodlands Resort

Shepherd’s Rock, Nemacolin Woodlands Resort, Farmington, PA:  You can be sure your sixth sense for sublime golf travel is working when you lock on to a course that isn’t even open yet. Beginning July 12, golf pilgrims can immerse themselves in the pure Pete Dye-ness of Shepherd’s Rock, the newest addition to this luxurious resort on 2,000 acres southeast of Pittsburgh. Modern earth-moving equipment can create landscape perfection; Dye understood this wasn’t desirable and spent a career making sure to exploit the quirks and peculiarities of natural terrain. There’s beauty throughout his courses, but never an overt glamour. Dye has a second course at Nemacolin, and the outdoor activities here are endless. For indoor enthusiasts, there’s a casino and multiple spas, plus a fine array of dining options.

Photo: Stowe Mountain Resort

Photo: Stowe Mountain Resort

Stowe Mountain Club, Stowe Resort, Stowe, VT: There’s nothing prettier than your own golf shot suspended in the air against a mountain vista on a long, downhill hole. This high-country course in the shadow of Mount Mansfield gives you several of those moments, most notably on the plunging par-3 16th. It took a design genius like Bob Cupp—he was a book illustrator and a master cabinet-maker, as well as a course architect—to wrangle this sloping, chasm-laced topography into 18 wonderfully playable holes. Lodge guests also have privileges at Stowe Country Club, built on more level ground but with wonderful views nonetheless. A summer highlight for locals and visitors is the Stoweflake Hot Air Balloon Festival, July 7-9; it’s a chance to see something almost as pretty as your golf shot, pinned against the ridgelines and peaks.

Note: Tradewind’s Ultimate Golf package can accommodate your entire trip to Stowe, thanks to a new partnership with Stowe Mountain Club. As part of a two-day getaway aboard an eight-person private charter, enjoy unlimited golf access to both Stowe Mountain Club and Stowe Country Club, luxury accommodations at Stowe Mountain Lodge with views of Mount Mansfield, group lunch at The Cottage at Stowe Mountain Club, curated gift bags, and four-packs of Lawson’s Sip of Sunshine local craft beer. For more information or to reserve, please contact [email protected] or 802-760-4703.

Photo: Courtesy of Keswick Hall & Golf Club / Ken May

Photo: Courtesy of Keswick Hall & Golf Club / Ken May

Full Cry, Keswick Hall, Charlottesville, VA: The classic manor-style building on high ground with a green expanse of fairways spreading out below—there’s no combination of those two elements more pleasing than what you’ll find at this stylish resort in fox-and-hounds country outside the university town of Charlottesville. Full Cry (that’s hunt-club vernacular) is an original name for a golf course, and this layout is loaded with originality and character—again courtesy of Pete Dye. Inside the beautifully restored Italianate hostelry, Keswick Hall, are just 48 guest rooms, each individually decorated. The place was in shambles until Sir Bernard Ashley, widower of design queen Laura Ashley, arrived bearing capital and good taste in 1995. Present ownership has taken it far beyond what even his lordship had achieved.

Photo: Omni Grove Park Inn

Photo: Omni Grove Park Inn

The Omni Grove Park Inn, Asheville, NC: Artsy and outdoorsy, but still with traditional Southern graces, Asheville belongs on any summertime pleasure tour. Guests at the Grove Park Inn return each year for the golf, great dining, and country hospitality. Donald Ross, a Johnny Appleseed of superior course-building, laid out the beloved Omni Grove Park Inn links in 1926, when shovels and mules were all you had to sculpt with—natural, unforced contours are the result. And while the craft beer movement and its bespoke breweries have sprouted all across the country, few cities can compete with Asheville, a suds mecca with more breweries per capita than anywhere else in the U.S. There is no end of ways to explore its malty wonders, including a half-day bus tour with many a tasting stop. Cheers.

Photo: Courtesy of The Sea Pines Resort / Rob Tipton

Photo: Courtesy of The Sea Pines Resort / Rob Tipton

Atlantic Dunes, The Sea Pines Resort, Hilton Head, SC: The concept of the resort golf community originated with Sea Pines, which retains a vague ‘60s-era imprint even as it continually updates and renovates itself. One of the courses was recently plowed under to make way for Atlantic Dunes, which opened last year and brought yet another round of acclaim to the course design group of Davis Love III (who as a player won the PGA Tour event at Sea Pines five times). Atlantic Dunes is visually sleek and stylish, with large greens, new and restored sand dunes, and little touches like crushed coquina shells and waving seaside grasses to frame the holes. For all the dozens of trips I’ve made to this resort, I’ve not yet had a chance to experience Atlantic Dunes. And yet I know instinctively that I would have a great time playing it.


*Featured Image: Nemacolin Woodlands Resort

On Deck with Sail Boston Executive Director Dusty Rhodes

On Deck with Sail Boston Executive Director Dusty Rhodes

Flying into Boston in mid-June? Make sure you look down.

A fabled fleet of tall ships with billowing spinnakers and streaming pennants, some that logged thousands of miles from across the seven seas, converge for Sail Boston in a glorious gam.

Part of the international Rendez-Vous 2017 Tall Ships Regatta, the six-day festival from June 17th through 22nd is the closest you can get to nautical nirvana without weighing anchor and embarking for distant ports.

“It’s the greatest show on surf,” says organizer Dusty Rhodes, and she should know.

Rhodes, Executive Director of Sail Boston 2017, is a prime architect of Boston’s vibrant, maritime spectacles. With an irresistible siren call, she began attracting processions of tall ships into Boston Harbor in 1992.

Dusty Rhodes, President of Conventures, Inc., joined by Boston Mayor Martin J. Walsh and Capt. John O'Connor.

Dusty Rhodes, President of Conventures, Inc., joined by Boston Mayor Martin J. Walsh and Capt. John O'Connor.

Back then, the harbor, with its famed “dirty water,” was the city’s neglected and undervalued backyard. Today it’s more coveted than the Back Bay. High-wattage events like Sail Boston, and a heavy dose of real estate investments, have turned the harbor into the Boston’s shimmering front yard—a new nexus of vitality.

At the helm of Sail Boston, Rhodes has prodded and wooed the most regal ships to sail into Boston Harbor this summer. As President of Boston event planning and communications company Conventures, her command of the harbor provides juice to her juggling act.

“There are only a handful of ports in the world that can handle these ships,” says Rhodes of the stately armada of two-masted schooners, square riggers, barques, ketches, and cutters—50-plus ships in all—dropping anchor here.

“They come from multiple countries. Some are floating embassies,” she says.

Hence, it’s no simple feat to coordinate their convergence.

Rendez-Vous Tall Ships Regatta by Boston Sail

The Chilean ship took perseverance and persuasion. Nevertheless, she persisted.

“We had to lobby to get them to change their sailing schedule to come on a special time and date. It takes years of lobbying and political influence,” says the confident Rhodes.

It sounds a bit like staging the Olympics, but with a difference: “The Olympics is easier,” says Rhodes. “They have an organizing committee.”

Similar to a Macy’s Thanksgiving Day Parade, these magnificent ships from another age inspire a child-like awe when they emerge from the deep, sailing into town under nothing but wind power.

So when one of the most influential women in Boston suggests the best way to experience the biggest draw this summer, take her advice. (This is on your bucket list; you just don’t know it yet).

Rendez-Vous Tall Ships Regatta by Boston Sail

“You want exclusivity?” she asks. Sign up for a deck reception to land that skittish client.

“It’s like the Kentucky Derby on steroids,” says Rhodes. Hats optional.

Imagine boarding a historic schooner, as the ship’s whistle heralds your arrival. Relax on the deck and entertain like an admiral.

Instead of sipping a mint julep at Churchill Downs, you could be enjoying a dark and stormy on a tall ship in Boston Harbor.

“It's a once in a lifetime experience; you don’t find that on the 19th hole of a golf course," says Rhodes.


Most of the events are free, but you can buy tickets to the Parade of Sail grandstand on June 17th for $125 each at To book a deck party, email [email protected].


*All photos courtesy of Sail Boston