The world is peppered with thousands of small islands. Many are beautiful, some stunning and some poor losers are ghastly ugly. Travellers dream of discovering one to call home, if only for a holiday.

Hanging off the coast of Massachusetts is a cluster of small islands. Not far from these islands were once some of the world’s most productive fishing grounds. Killing fleets nearly eradicated whales from the whole of the North Atlantic. Overfishing killed the golden goose while whale oil was finally replaced by petroleum. Those days are past. These days see better management practices in place while fish stocks recover. Still, fortunes made off huge catches are the stuff of memory.

Menemsha harbor is still a working fishing port.

Money is made in the big cities nowadays, Boston, Hartford, Providence and New York. Banking, stock markets, insurance and financial services lead to big incomes. Where do local rich people play if they don’t want to venture far from home?

The Hamptons at Long Island’s end and Newport at Rhode Island’s bottom come to mind when thinking of ubiquitous wealth and ostentatious spending. Both places attract old money and new money in apparently equal measures.  The islands off Massachusetts are also well known as an American moneyed set’s playground.

Hyannis on the mainland is the gateway port for Nantucket and Martha’s Vineyard. The Kennedy family compound is at Hyannis overlooking Nantucket Sound, a yachtsman’s paradise of shallow clean water with safe anchorages on the islands’ northern shores and all along the mainland.

If the world was perfect it would be a lot like Martha’s Vineyard. The world isn’t perfect so little spots like Martha’s Vineyard perform stand-in roles in global theatre’s constantly travelling play, ‘The Search for Perfection’.

I was seduced by Martha’s Vineyard right from my first impression. Its tourism officials are some of the friendliest people I’ve dealt with on a professional basis. What swept me off my feet was the frank honesty about their little island. Amidst all that wealth, the people employed to spruik the island’s attractions showed genuine humility delightfully paired with frank humour. Expecting a wade through a bath of bullshit, I was surprised instead by undressed honesty. PR spin was reeled out at a bare minimum, if at all.

Edgartown church and visitor’s center.

What separates prosperous Hamptons and Newport from Martha’s Vineyard is the difference between blatant show and not much substance and discreet show with a lot of substance. Inconspicuous wealth is the key to Martha’s Vineyard’s charm.

And the fact that much of that money has gone into protecting the island’s environment.

Edgartown is the island’s big town. It ranks as one of the prettiest villages in all the USA. Across the narrow channel from the town harbour is tiny Chappaquiddick, an island off an island but considered part of Edgartown.

Typical Edgartown houses.

The island’s main library is in Edgartown as is the town hall and administrative offices. Lots of tiny shops, cafes and a few restaurants complete the tidy tourist picture. A photogenic lighthouse juts up from the sand dune off Edgartown’s harbour front, signalling the passage between Chappaquiddick and central Edgartown.

During a mid-spring visit, I got the impression that many of Edgartown’s houses are essentially summer homes for holidaying semi-permanent residents. The average cost for a moderate house in Edgartown is over USD$ 1 million.

Edgartown North Water St former sea captain houses.

Outside the busy summer season, the island’s other town of consequence, Vineyard Haven/Oak Bluffs is where the majority of the island’s permanent residents hang out and live. Vineyard Haven is the island’s ferry port to the mainland, crowded with maritime businesses compared to Edgartown’s leisurely yachting sidelines. While Edgartown seemed to be in a napping state before summer’s onslaught of visitors, little Vineyard Haven thrummed with life.

I’ve noticed a queer fact about human living patterns; no matter how small the living area is people will separate themselves into sections. Martha’s Vineyard, approximately 30 kilometres long by 15 kilometres wide is divided into Up Island and Down Island. Up Island is west of Vineyard Haven/Oak Bluffs, consisting of hamlets like North Tisbury, West Tisbury, Aquinnah, Chilmark and Menemsha. Up Island officially ends at Gay Head, a series of bluffs facing into the North Atlantic Ocean. I hear the local council has a challenging time maintaining its Gay Head signs, theft is common and vandals make the most of Gay Head’s punning opportunities.

Gay Head sign.

Down Island are Edgartown and Chappaquiddick. Considering that only about 16,000 people call ‘The Vineyard’ home all year round, I was surprised the community has split itself pretty much right down the middle. Up Islanders tend to be permanent residents. Down Islanders tend to be semi-permanent.

To make geographical matters even more complicated, a fierce rivalry exists between ‘The Vineyard’ and nearby neighbour, Nantucket Island. ‘Martha’s Vineyard has hills. Nantucket is flat.’ ‘The Vineyard is open to visitors, Nantucket isn’t.’ After a couple days I just had to accept a majority opinion, ‘Nantucket is weird.’

I look forward to visiting Nantucket to find out for myself.

Martha’s Vineyard is a popular place. Keep this fact in perspective: during summer’s peak season June, July and August, the island’s population swells to over 100,000 people, almost ten times the average population. That almost everyone manages to maintain a friendly outlook during the summer rush of visitors is testament to the island’s innate attraction. It’s as if everyone has decided to adopt a democratically positive attitude. Why be bothered to sulk in such a peaceful environment?

US Presidents holiday at Martha’s Vineyard; it’s that private. Obama and his family rented a secluded house Up Island early during his presidency. Bill and Hillary Clinton sailed off its shores during several executive office breaks. Of course members of the Kennedy clan have been making regular visits since the 40s. Some of those visits became notorious. Remember Ted Kennedy’s car accident in 1969?  He drove off a bridge on Chappaquiddick; survived the crash but his secretary Mary Jo Kopechne didn’t. She drowned in the back seat. Kennedy reported the accident to local police some hours later. He had found time to dry his clothes but his hopes for a successful run at the presidency were dashed forever.

Steven Spielberg took a liking to the island and used it as the setting for his ground-breaking film ‘Jaws’. A number of local kids appeared in it. A local company operates random ‘Jaws’ tours of the island by appointment. One of the kids who appeared as a film extra apparently works as a guide.

What to do on Martha’s Vineyard? Officially speaking there are no major tourist attractions. A great part of the island’s charm is that no chain restaurants, theme parks, retail conglomerates or very important significant historic sites exist. Is it the perfect contemporary mass marketing vacuum? Thankfully yes.

Sunset at Felix Neck.

For me it’s one of those rare places where I didn’t feel compelled to do anything other than to wander blithely experiencing one kismet moment after another: a spectacular sunset on the sandy road between Oak Bluffs and Edgartown looking towards Felix Neck Wildlife Sanctuary. Chatting with a shopkeeper at Menemsha’s little port, him boasting that he made the island’s best clam chowder. Large empty cans of watery potatoes in his small kitchen had me wondering at his comical bluster. “Why don’t you use fresh potatoes?” I asked. “People seem to like it this way. You want some or not?” I left smiling but didn’t try the canned chowder.

Menemsha Fish Market, home of the island’s ‘best’ clam chowder.

Meeting a 60 something couple walking their dog at Lambert Cove beach, one of the island’s prettiest. We were the only people there. She works as an itinerant housecleaner in luxurious summer homes rented by rich visitors. Her retired partner spends most of the year on the mainland near Barnstable doing odd jobs but “loves” the Vineyard. He returns to the island to see her and get away from mainland life’s trials and tribulations. They were so much in love it was a glad day just to walk with them along the beach while they told me all about living on the “most beautiful island in the whole northeast”. I learnt much from them about the social divides between wealthy residents and those less fortunate, a largely live and let live co-existence. Another moment was richly felt while exploring the excellent Vineyard Haven Bookshop and Art Gallery with its lovely collection of works by local artists and a fine selection of thoughtfully chosen books. Yet another was spent chatting with a librarian at Edgartown’s esteemed and well-used town library. Asking him about the original inhabitants, the Wampanoag tribe, I was invited into his office for a long informative chat about the tribe’s long fought battle to secure a permanent landholding at Aquinnah. Other fine moments were spent briefly stopping my rental vehicle three separate times so families of Canadian geese could cross safely, goslings waddling behind parents as fast as their little legs could carry them. Passersby waved at me as did fellow drivers, cheering goose commuters onwards? Finally, after a long day spent collecting snippets of island life far-reaching insight was captured while standing alone at Gay Head looking out over the vastness of the North Atlantic imagining how little the island had changed in 10,000 years. That’s my short list of serendipitous moments during a day of wonder on the perfect island.

Lambert Cove beach.

Had I another spare day I would have hired a bicycle and made use of the island’s extensive bike trails.

Dreaming of that possibility had I another spare day in addition to the cycling day, I would have made better use of the island’s extensive walking trails.

A subsequent spare day would have been spent sitting on the veranda of my hotel reading a book, perhaps ‘Caleb’s Crossing’ by resident author and ex-pat Australian Geraldine Brooks.

Fantasising about days spent idling on a perfect island is a contagious mindset.

Martha’s Vineyard conjures scenes of director Peter Weir’s 1998 film ‘The Truman Show’ with Jim Carrey, Laura Linney and Ed Harris. It’s the sort of place that engenders comparisons with impossibly perfect places. Fairly or unfairly, the small island cops criticism for being elitist and separatist. I don’t agree. For me, ‘The Vineyard’ is a microcosm of American current reality. Dig deep enough and financial stress coupled with economic troubles is uncovered easily enough even on this speck of overriding affluence. But that’s not what this holiday island is all about. Largely it’s a dream made real where the living is relatively easy and ostentatious wealth is frowned upon by the wealthy and middle class alike. 

Aquinnah cliffs.

Since 2008, much social media discussion has revolved around how America has changed from a land of opportunity for everyone to a land of opportunity for the already rich. Statistics bear out the truth of this accusation as increased wealth rests in fewer select hands while the poor struggle to hold on to a diminishing portion of the gross national fortune.

Oldest house in Edgartown, a reminder of when the island was poor.

Martha’s Vineyard is one of those rare places in the USA where it’s possible to witness how great wealth held closely in the hands of the few is clearly juxtaposed with moderate means in the hands of many. They co-habit with a visible degree of equanimity, each possessed of their inalienable right to a good life whatever its price.

Is this an island ethos driven by an absence of envy?

Probably not, but nowhere is perfect.

Tom Neal Tacker travelled courtesy of Qantas Airways and Massachusetts Tourism Authority.

Naked Routes:

Getting to Martha’s Vineyard is easy. During high season daily ferries run between Hyannis, Falmouth and Fairhaven, Massachusetts’ ports only a few hours sailing time to Vineyard Haven. I flew as a guest of Massachusetts Tourism authority on Cape Air from Boston and from the island to Hyannis. The two hops in 10 seater twin-prop Cessna aircraft were geographical revelations. The flight path takes in Boston Bay, the Upper Cape and Nantucket Sound. On a clear day, it’s a wonderful trip. See www.capeair.com for information and bookings.

Naked Sleeps:

Martha’s Vineyard tourism hosts looked after me splendidly. I was lodged for two nights in one of the island’s best hostelries, The Harbor View hotel in Edgartown. Overlooking Edgartown’s picturesque harbour and lighthouse with Chappaquiddick’s beach lights twinkling in the near distance at night, it’s a terrific hotel comprising one grandly renovated building with a huge sea-front veranda and several converted out buildings, formerly private residences from the days when Edgartown made its money from whaling and fishing, all set in manicured gardens lending an added atmosphere of space and exclusivity. Local birds loved the gardens too. My suite on the upper level in one of the old refurbished sea captain’s houses was faultless: full king sized bed made up with luxurious linens in an enormous bedroom with an open fireplace, separate dressing room, bathroom big enough for a whale with huge tub and separate shower, sitting room with another open fireplace, leather lounges, large table and armchairs made it seem like a home instead of a hotel. Two wide screen televisions, a good music system and free wi-fi brought me back to modern reality. It was absolutely private and very quiet. The hotel’s free private off-street parking away from Edgartown’s narrow streets was also a bonus. Service was kind, friendly and absolutely genuine. Breakfasts are cooked to order and served by gracious and friendly waiters in a cheerily sunny conservatory in the main building. Thank goodness, it’s a no buffet zone. Steam baths filled with gluggy scrambled eggs, soggy bacon and old toast aren’t in keeping with the Harbor View style. Freshly squeezed juices were complimented by an espresso machine that employees knew how to operate. In the land that coffee has essentially forgot, this was also a real bonus. Sunset cocktails in the lobby bar were the icing on a grand accommodation cake. It’s pricey but well worth the spend.

See www.harbor-view.com for reservations and information. Prices are from USD$476 per night.

Harbor View hotel in Edgartown.

Naked Eats:

New England’s coastal communities are justifiably famous for seafood and fish, particularly now that fisheries are managed more sustainably. Clam chowder is basically the state of Massachusetts official dish, despite Boston beans alternative claim to the local culinary crown. Lobster is widely available at a price. Sadly, it’s a crustacean that is poorly understood by many local chefs who continue to overcook it to a rubbery death. Maybe ask to have it served rare? Same rule applies to scallops and clams. Don’t overcook either. Local oysters are also a revered delicacy. At least they weren’t cooked.

Martha’s Vineyard’s local clientele is fairly savvy. What else would one expect in such educated surrounds? I ate well from simple menus (in off season) at The Offshore Alehouse in Oak Bluffs (30 Kennebec Ave Tel: +1 508 693 2626) and the Martha’s Vineyard Chowder House Company (9 Oak Bluffs Ave Tel: +1 508 696 3000) also in Oak Bluffs, both unstuffy restaurants with loyal local followers. These were not really tourist restaurants as they stay open out of season to cater for the island’s permanent inhabitants. They both sport popular bars with bartenders who know how to make a cocktail with a generous pour.

Many of The Vineyard’s restaurants fine diners are open only during high season from May through to October.

Check out the West Tisbury Farmer’s Market on Wednesdays and Saturdays (Tel: +1 508 693 9561), the Mermaid Farm in Chilmark (Tel: +1 508 645 3492), the Fiddlehead Farmstand in Vineyard Haven (Tel: +1 508 696 6700) and Eden Market & Garden Center also in Vineyard Haven (Tel: +1 508 693 5202) for the best of the island’s farm produce including raw milk products, local stone fruits picked fresh during summer and locally made jams, mustards and honey. Menemsha has a fisherman’s co-op store selling fish and seafood fresh off the boats, open most days even in off season.

See www.mvy.com or www.massvacation.com for more information about accommodation, island-mainland transport options, seasonal activities and local festivals and events.