America’s billionaire’s retreats in incredible archive photos

Former fishing ports turned billionaire playgrounds

Off the coast of Cape Cod, Massachusetts, sit two idyllic islands, Martha’s Vineyard and Nantucket. They were originally home to the Wampanoag people, who dubbed the latter island ‘The Faraway Land’ due to its tranquillity and remoteness.

Over the centuries, the islands have developed from hardworking whaling harbour towns to playgrounds for presidents and celebrities, synonymous with wealth and exclusivity. Home life through the ages has undergone enormous changes.

How did two such tiny islands carve out such a substantial reputation? Click or scroll to learn more…

Massachusetts whaling

Long inhabited by the Wampanoag people, Martha’s Vineyard was officially 'settled' in 1642. The Wampanoags taught the English arrivals how to hunt whales and boil oil out of the blubber, which became the island’s major export.

Nantucket was established in 1659 and quickly became one of New England’s major whaling ports from 1750 to 1840. Whales were a valuable commodity for their meat, bones and especially oil, which was used in gas lamps. 

A dangerous profession

However, whale hunting was a hazardous industry, which led to many deaths and resulted in countless widows back on shore.

By the 1880s, whaling was a dying industry, largely due to the significant depletion of the local whale population and the development of safer local trades.

However, the seafaring industries had already left an indelible mark on the architecture and culture of the two islands. These lobstermen shacks of the 1890s on Martha's Vineyard were a typical home for the families that made a living from the waters.

Harbourside accomodation

The domestic architecture of both islands became dictated by the social hierarchy associated with the fishing and whaling industries.

Lower-ranking sailors and seamen generally rented rooms in cramped lodging houses near the busy ports, seen in the backdrop here, which offered access to any ships which might be hiring crew members.

These lodgings were temporary accommodation rather than permanent homes, as many professional sailors moved from port to port around New England, or even around the world, as the job required.

Captains' cottages

‘Captains’ cottages,’ as the elegant homes belonging to the wealthier ship captains came to be known, were far more distinctive, permanent island residences.

These homes were usually positioned on the finest streets, within easy reach of both the water and the town centre, and were built in either the Georgian or Federal style.

Characteristic features included white columned entryways, white cladding on the front at a minimum, if not around the whole house, and cupolas or widow’s walks.

Comfortable interiors

Inside, the homes were filled with the accoutrements and furnishings of any moderately wealthy New England house. Whitewashed walls, Quaker wood furnishings, woven matting, or Oriental carpets and English pewter and china would have been staples, but still luxuries for the time.

Homes were warmed by large fireplaces, usually one on each side of the house on every floor, and lit in the evenings by tapers or oil lamps fuelled by, you guessed it, whale oil.

Characteristic architecture

Pictured here is the interior of a typical 19th-century island captain’s cottage, which has been restored and preserved by the Historic American Buildings Survey.

Characterised by its simple wood-frame structure, utilitarian trim, shingled exterior, gambrel roof, and central hearth, this is a quintessential example of Nantucket architecture from that time.

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Lighthouse living

Island architecture for the more permanent residents, who might not have taken to the high seas, but whose work was no less essential to the maritime trade, included lighthouses.

They played a critical role in the fishing and whaling industries, guiding ships safely to shore on dark and stormy nights.

Lighthouse keepers lived on site full-time, residing in cottages either attached or adjacent to the lighthouses themselves, like the one pictured on Nantucket here. Some attracted famous faces...

The Gilbreth family

In 1838, this lighthouse was built on the north shore of Nantucket, between the beach cliff edge and Cobblestone Hill. In 1908, the government decommissioned it and replaced it with smaller ones further down the coast.

Famed engineer Frank Gilbreth and his wife Lillian came to Nantucket in the spring of 1918, looking for a beachfront property where Frank could recover from a wartime illness. They found and fell in love with the quirky remains of the lighthouse station. 

The Gilbreth family are the famous Cheaper by the Dozen family, with their lives being portrayed in both book and film. They became a permanent fixture on Nantucket, visiting almost every summer. Here they are in 1923.

Mid-19th century decline

As the Golden Age of Whaling began to die off, the fortunes of both islands dwindled, with many islanders opting to leave and seek their livelihoods elsewhere.

Nantucket and Martha’s Vineyard both saw significant population decline in the mid-19th century. It was the result of a combination of factors, including the growth of the railroad industry, the discovery of gold out west, the onset of the Civil War (and on Nantucket specifically), plus a devastating fire which tore through the heart of the business district and destroyed the majority of the wharves.

Tourists arrive

By the turn of the new century, Nantucket had become a tourist hub, attracting affluent New Englanders looking to escape summer city heat for island breezes, beautiful beaches and rolling farmland.

Efforts had been made to preserve the island’s unique charm and character, and its cobbled streets and weatherboard ‘captains’ cottages’ remained largely intact thanks to the creation of the Nantucket Historic District.

An architectural revival

However, a huge surge in tourism in the early 1900s saw wealthy city dwellers buying and restoring the now-abandoned and languishing captains’ cottages to use as summer homes.

Fortunately, in an odd twist of fate, the islands’ dwindling income had left little money for new development, so most 18th and 19th-century cottages still stood, their architecture preserved and ready for restoration.

This captain's house in 1934 kept its classic facade, complete with widow's walk atop its roof, but would likely have been completely redone inside.

New business

As the islands’ economies ground back into life, new industries began popping up to accommodate the influx of tourists.

Pictured here, pedestrians traverse the busy boardwalk on Commonwealth Square on Martha’s Vineyard, which boasts a range of new businesses including Howard House Hotel, Tucker’s Bakery, the Mayhew & Luce hardware store, RH Piper's Eating House, and Otis Foss's dry goods store.

New construction

As the 20th century progressed, many summer holidaymakers found themselves wanting more than a mere restored captain’s cottage, and began investing in new builds like Nantucket’s ‘The Breakers,’ pictured here.

While architecturally faithful to the islands’ original weathered, clapboard-clad homes, these properties were built on a much larger scale, designed for hosting large house parties, and inviting a whole new social set of arrivals...

Famous faces on the islands

By the mid-20th century, Nantucket and Martha’s Vineyard’s charms were attracting the social elite as well as the wealthy. Pictured here, First Lady Eleanor Roosevelt relaxes outside a Martha’s Vineyard cottage belonging to celebrated actress Katherine Cornell, alongside Helen Keller, with whom she became friends in later life.

Eleanor spoke warmly of both Nantucket and Martha’s Vineyard in her many writings, and even acknowledged the “fairly vigorous” rivalry which had recently arisen between the two, but stating diplomatically that she “found both of them delightful.”

Presidents on Martha's Vineyard

As the islands rose in renown, more famous faces began appearing around the islands, particularly during the summer months.

Perhaps taking Roosevelt’s lead, many presidents chose to vacation on Martha’s Vineyard, including Ulysses S. Grant, John F. Kennedy (pictured here with Jackie), Bill Clinton, and Barack Obama.

These visits understandably raised the island’s profile, establishing it as the ultimate, elegant summer retreat for East Coast Americans.

The Obamas

The Obamas made a home on Martha's Vineyard, going so far as to buy a house in 2020 just outside of Edgartown. It had nearly 30 secluded acres (12ha) overlooking a beautiful pond in a ‘neighbourhood’ which had previously been home to the likes of Jackie Kennedy Onassis, Jeffrey Kramer, Spike Lee, and Oprah Winfrey.

The Obamas spent their first summer on the Vineyard in 2009 and returned every year of Barack’s presidency. He is pictured here taking a call with then-Canadian Prime Minister Stephen Harper in the living room of his former home.

Celebrities on Nantucket

Nantucket, meanwhile, has often played host to the billionaire set, including Bill Gates and Warren Buffett.

The island is regularly visited by A-listers such as Beyoncé and Jay-Z, Amy Poehler, Steve Carell, and Ben Stiller. Politicians also made their homes here, including former Secretary of State John Kerry, whose impressive house is pictured here.

Taste-making designer Tommy Hilfiger also once owned an expansive estate named Point of View, overlooking the Nantucket Sound, and has confessed that the island's lifestyle helped inspire some of his designs.

The gingerbread cottages

The islands are both home to a host of quirky homes, tremendously popular with tourists and locals alike. One of Martha’s Vineyard’s particular highlights is the Oak Bluffs 'gingerbread cottages', pictured here in all their colourful glory.

These playful homes have their roots in the Methodist camp meeting grounds of the 1800s, during which the island became home to this particular religious group.

Religious inspiration

While the Methodists originally camped out in tents, they soon realised that cottages were better suited to withstand the weather.

These cottages were built to resemble the tents they replaced, with steeply pitched rooflines and double front doors to resemble tent flaps. They feature highly decorative woodwork made possible by the invention of the power-driven jigsaw.

Illumination Night

Today, the original cottages have been lovingly preserved and painted in bright, cheerful colours, making them one of Martha’s Vineyard’s most iconic landmarks.

Every summer, the island celebrates Illumination Night, during which all the Gingerbread Cottages are decorated with lights and coloured lanterns.

Nantucket Film Festival

The 1975 action-thriller Jaws was filmed on Martha's Vineyard, acting as a huge tourism draw for the island.

Not to be outdone in the two islands’ well-established rivalry, Nantucket’s answer to the Jaws craze is an entire film festival, established in 1996 and held annually.

The festival focuses on screenwriting and is also associated with the Screenwriters Colony, an all-expenses-paid writers' retreat on the island. The writers often stay at Almanack Pond Farm.

A remarkable journey

It’s safe to say that Nantucket and Martha’s Vineyard have both come a long way from their humble, seafaring beginnings.

Now synonymous with luxury, exclusivity and the East Coast elite, the islands have come to hold a sociocultural influence disproportionate to their size, spanning everything from film to fashion, to architecture and beyond.

No matter your reasons for swapping the rat race for ‘the Far Away Land,’ one thing is clear: it’s good to be on island time.

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