Faraway Martha's Vineyard: A (New) New England Escape


“Summer afternoon—summer afternoon; to me, those have always been the two most beautiful words in the English language.”

Henry James’s famous words echoed in my ear as I disembarked from the ferry and walked out onto the wooden dock in Oak Bluffs. I was arriving from Newport — Henry James’s resort town of choice — and felt the immediate sensation, both freeing and disorienting, of being in someone else’s favorite place, an outsider amongst the locals and the summer residents, who were themselves aligned in an uneasy truce. Any level of residency is favorable to the weekend interloper, with their tell-tale canvas duffels and oversized totes, as if you were planning for just a day at the beach but ended up staying for more than 72 hours. 

The exclusivity of New England resort towns is both their appeal and their detriment. Summer people, some are not. Of course, as a travel writer, I love the thrill of impenetrable places — whether it be the arctic tundra of Lapland or a cocktail party in Edgartown. Often, you need to feel inside this social fabric — to feel like you belong — to truly appreciate the eternal charms of these seaside towns. Luckily, with the July opening of the Vineyard’s newest boutique hotel, it’s easier than ever for someplace quite far away to feel like home.

September Grass

A historic property gets a second act.

The gorgeous pool deck at Faraway Martha's Vineyard

(Image provided by Faraway)

Though I absolutely loved my recent stay, the opening of Faraway Martha’s Vineyard was far from a guaranteed success, particularly on an island resistant to change. Faraway was formerly the Kelley House, the fifth oldest hotel in America, which first originated as a tiny tavern in 1742. To bring the property into the 21st century while preserving its historical significance and unique charm was no small task — particularly in Edgartown, where the tight-knit community is well aware of all the newest comings and goings — business-wise and socially, too — downtown. And here, too, the owners’ knowledge and reverence for the island soothed the anxieties of locals who hate to see change of any kind. Why mess with perfection?

Though Faraway has established itself as an island favorite on Nantucket, that’s no bellwether for Edgartown. In fact, it’s partially Nantucket’s modernity, particularly of the conspicuously capitalist variety — those luxury hotels, the $400 dinners — that many Vineyard residents find off-putting. But Blue Flag won over locals’ hesitancy by preserving the property's framework and ensuring the historic on-site restaurant, The Newes From America, remained untouched.

The new owners juxtaposed the classic with the contemporary, preserving the framework of the architecture while incorporating innovative, luxurious touches and implementing the high-end service industry standards (and high-speed Wifi) you’d normally find in a city to a nearly three-hundred-year-old property. The property comprises six homes that once belonged to old sea captains. My cottage, Chappy, blended in so well with the classic Cape Codders lining the street that I passed it by twice on my walk home, certain it was another domestic residence — and it looked like one, right down to the brick path and purple hydrangeas. 

In fact, at Faraway Martha’s Vineyard, it’s easier than ever to feel like a summer regular in Edgartown.  Perhaps that's because the new owners are deeply familiar with the island already. Jason Brown, one of the partners at Blue Flag, the Boston-based real estate development firm that acquired the property, grew up spending summers in Chappaquiddick. He knows what visitors are looking for when they come to the Vineyard (affectionately known as ‘The Rock’): shingled cottages that feel like private beach homes, a relaxed ambiance, and sophisticated yet chic decor — the environs are certainly more elegant than your own home (and sparklingly clean), but it’s not too stuffy that you’ll ruin things. 

The Blue Flag group is familiar with the islands off the Massachusetts coast — their first Faraway property is on Nantucket. Crucially, both outposts are located in prime destinations downtown. If you aren’t a part of the social fabric of a tiny island and don’t have dinner parties every night, then you’re dining in town, and the Faraway Martha’s Vineyard is close to a plethora of great restaurants in Edgartown. Check out the live music and raw bar at Port Hunter, sip pre-dinner sundowners on the Adirondack chairs on the terrace of the Harbor View Hotel before slipping inside for a more formal dinner at Bettini, or check out the lively dinner and bar scene at Alchemy, right in the center of town — just remember to order the homemade ice cream for dessert.

Additionally, if you aren’t in possession of a yacht club membership, you’ll need a place to swim — especially considering many beaches in Martha’s Vineyard are private or require parking permits. Luckily, Faraway is steps from Edgartown Harbor and only a short scenic walk from Lighthouse Beach, which is public but has limited parking — not an issue for Faraway guests. Additionally, Faraway boasts a secluded swimming pool and hot tub with lounge chairs, striped umbrellas, and a wet bar tucked away amidst the historic cottages. Though the property is right in town, it feels — aptly — far away.

Country Road

Island living in downtown Edgartown.

A bar and patio lit by beautiful hanging lamps

(Image provided by Faraway)

The second Faraway outpost on Martha’s Vineyard has some marked design departures from the flagship on Nantucket, befitting each destination's storied lore and distinct identity — both islands have achieved cult status along the East Coast and beyond. While Faraway Nantucket is more maximalist, Faraway Martha’s Vineyard reflects a more bohemian, mid-century modern vibe, with decor inspired by the island’s flora (which you will find in full-bloom on your many walks throughout Edgartown). Faraway Martha’s Vineyard resists the lazy coastal decor that is a mainstay at so many island resorts — even the ultra-luxurious properties can’t resist a painted conch shell or pastel watercolor of the horizon. 

Faraway is far more understated, exuding a modern maritime seaside vibe designed for the 21st century with a distinctly whimsical flair — and this, too, is true to the island's heritage.

“While Nantucket is for business tycoons, Martha’s Vineyard is for artists,” states Brown.

In fact, the hotel is inspired by the artistic stylings of long-time Martha’s Vineyard residents James Taylor and Carly Simon — you will find their vintage vinyl records on display in your cottage. (Carly Simon won the island in the break-up: she remains a farm owner in Vineyard Haven. James Taylor, meanwhile, set sail for a different East Coast enclave: Jamestown, Rhode Island — arguably the Martha’s Vineyard to Newport’s Nantucket: less manicured and more low-key than the Gatsby-esque parties at the gaudy Bellevue mansions across the Pell Bridge, but the salt air is no less rarified). 

Nevertheless, they were once the hottest item on the island — and American culture at large — and the pair’s breezy 1970s vibe — laid-back glamor, straw hats perched atop wind-tousled hair, and faded blue jeans — permeates the property, infusing the whole place with a classic vintage cool that money can’t buy — no matter how many linen kaftans you purchase at NellRags, or The Shop, Faraway’s on-site boutique that serves coffee as well as sundresses. (I found the shopping in Edgartown to be incredibly curated, with a better selection of resort wear than Newport and Nantucket combined — all of it dangerously close to the hotel). 

But there’s more to Martha’s Vineyard than just retail therapy, of course. Take the Chappy Ferry — which queues conveniently one street behind Faraway — and head over to Chappaquidick (Chappy to locals), an idyllic island that, though it’s located just across the water from Edgartown, feels like hundreds of nautical miles away in attitude. In fact, there’s only one business on the island — the one-room Chappy Store — and the rest is tall grass, wide sandy beaches, and country roads. 

If you’re in for some local action, catch an evening game of the Martha’s Vineyard Sharks, a collegiate summer baseball team whose name references the famed film Jaws, which takes place on Martha’s Vineyard — a rewatch of which is always recommended on a visit to the island. For less frightening animal encounters, head to the Island Alpaca Farm to commune with some furry friends. Additionally, the MV Museum in Vineyard Haven provides fascinating context for the centuries of history in Martha’s Vineyard — whaling was once the primary fuel for the economy (pun intended), and the island was a whaling capital for 156 years (1738 to 1894). Today, a trip to the island is incomplete without heading out to sea. Set sail in the fleets of yesteryear with a Black Dog Tall Ships sailing charter, which offers both day and sunset sails.

How Sweet It Is

Home far away from home.

A lighthouse on a lake at dusk

(Image provided by Faraway)

A stay at Faraway provides a taste of the certain je ne sais quoi of Martha’s Vineyard, and that feeling is addictive. Less accessible than Cape Cod (26 nautical miles, or a 45-minute ferry, off-shore), the Vineyard is also less prominent in the cultural imagination — thanks to the Kennedys, residents of all 50 states can picture the 35th president at the helm of his 25-foot sailboat, all-American cool in Ray Ban Clubmasters while navigating the waters off Hyannis Port.  Interestingly, Jackie preferred Martha’s Vineyard to Cape Cod, choosing to spend her summers in later years on her 340-acre estate in Aquinnah — and wasn’t she the true architect of Camelot? The one famously known for her discretion and taste? 

Today the Obamas carry the torch for presidential leisure on the island — the family’s Edgartown compound was the site of the former president’s much-criticized 60th birthday party. The locals felt free to grumble about the interference to the press — one difference that sets Martha’s Vineyard apart from its main rival across the Atlantic: On Nantucket, celebrity is cause for celebration, not chagrin. To be fair, it’s not so much a rivalry as a distaste, an aversion. It’s too crowded, with overpriced restaurants, and flooded with weekend visitors who skip the Vineyard and head out 26 nautical miles further to sea to reach Nantucket. 

In full transparency, I arrived on Martha’s Vineyard after a week spent on Nantucket — yes, reader, I am part of the weekend riff-raff, the flotsam, and jetsam, though to be fair, I was a houseguest at a friend’s family summer home. (Though prior visits have seen me sleeping three to a bunk bed or taking midnight cat naps on a lifeguard stand at Jetties Beach — in all fairness, I was barely out of college). But when you’re renting an Airbnb from some all-knowing, omniscient homeowner — you may never see them, but they’re somehow always seeing you  (especially when you misbehave) — or dropping your sandy beach bag on the parquet floor of some sterile, nondescript hotel room (which is somehow always exorbitantly priced), it’s hard not to feel like a juvenile post-adolescent. And if so, what’s the point?

Faraway makes you feel at home. The cottages make you feel like you own the entire residence, with balconies, sitting rooms, and ocean views. If you can’t live out your Nancy Meyers fantasies on a weekend trip to the Vineyard, when can you? I certainly had my movie star dreams come true on my return journey home. Though there are fast ferries — such as the one I boarded in Orient Point, there is also a new partnership with Faraway and Tradewind Aviation — which is how I found myself flying private (by accident) when I was the only passenger on my charter to Million Air in Westchester. (And yes, that name is real). When I landed in New York, I immediately longed for my next return visit to the island. Summer people, some are not, but maybe — with a little help — the rest of us can learn.

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