Something you may not have realised about your old columnist is that I’ve always had a soft spot for pirates, going way back before the late and lamented Brother Buffett immortalised that line about how a pirate looks at 40, and generations before Johnny Depp’s brilliant impersonations of Keith Richards.
Which is why I have always been fascinated not just with the waters of the Caribbean, but with the cooler currents of the whole of the American eastern seaboard, along which, long before 1776 and all that, a lusty breed of scalliwags, rascals and psychopaths established their own code of independence by doing whatever they damn well liked.
The last time we explored this pirates’ playground was about a decade ago from the southern end in various parts of Cuba – where we were almost scuttled in the back streets of Havana by a fake cab driver— and Key West, Florida. But this time round what provoked the trip was the delight of receiving in the post that rare thing these days – something of interest. In this instance it was a letter from one of the most strangely loveable modern day pirates still operating, none other than Dirty Dave (aka the Wombat Warrior), once an Aussie but for many decades on the run in strange parts. This missive, obviously constructed by someone with far more style and erudition than Dave himself, advised that this writer and better half would be welcome to attend a family wedding on remote Squaw Island where the extended family was currently hiding out.
A little Googling revealed that Squaw Island is actually a seaward section of Hyannis Port on Cape Cod, where piracy has been a way of life for more than four centuries, and is an ongoing pursuit, courtesy of the famous Kennedy clan. This was an opportunity too good to pass up, so I hurriedly advised we would be in attendance and started selling toys surplus to requirements (like any surfboards under nine feet) to pay for the tickets. We’ll get to the riotous rorts that ensued on Squaw Island and on the waters of Nantucket Sound in a minute, but first let me give you a brief potted history of Hyannis.
Taking its name from Hyannough, a Native American chieftain whose clans had occupied the harbour area, Hyannis was first settled by English farmers in 1602, and incorporated as part of the Town of Barnstable in 1639, making it one of the oldest towns in America. By the 18th century, over 200 shipmasters had dwellings in Hyannis as the area became known as “the Port”, which covered a multitude of the kind of sins usually found on pioneer waterfronts.
Take, for example, the tale of Black Sam Belamy, a pirate who in 1715 hijacked the 100-foot slave ship Whydah Gally, not long after it had left Jamaica on its maiden voyage.
The captain and his crew used the Whydah to pirate other ships before eventually sailing north towards Wellfleet, just along the coast from Hyannis. But the Whydah Gally never reached its destination. The pirate crew was too drunk to finish the journey and the ship came afoul of a powerful nor’easter on the night of 26 April 1717.
Although they were within sight of land, the Whydah crew couldn’t navigate the storm and slammed stern-first into a sandbar, breaking apart. Only two of the 146 men on board survived the wreck. It was believed that Sam’s ship contained treasure plundered from 53 other vessels, and as news spread about the Whydah’s lost fortune, people flocked to the beaches around Hyannis, hoping to pick up a spot of it, creating a trend that continues today with pretty young things prowling around the edges of the Kennedy Compound, hoping to land a big fish.
Hyannis was a low-key playground of the rich and famous, considered more relaxed than Newport, Rhode Island or Bar Harbor, Maine, long before Boston banker Joe Kennedy rented a summer house on the edge of the harbour in the early 1920s, and began a family takeover of the village. Soon he had moved on from banking to being a film mogul and was famous locally for entertaining screen siren Gloria Swanson in one of the houses in the compound while wife Rose was in another watching her boys, Joe Jr, Jack and Bobby chatting up chicks on the beach.
You have to love this place of understated Cape Cod shingle houses with Adirondack chairs on the lawns and a cruising yacht moored out front. And it’s got such history. In 1962 JFK solved the Cuban Missile Crisis while strolling the sand in front of the compound. Just across the water a few years later, Teddy drove a car off a bridge and killed a girl. After his senatorial career was over, he lived in the Hyannis compound until his death in 2009.
But cutting to the chase, the wedding was wonderful, we looked for surf and there was none, but Dirty Dave and I had fun out on the Sound with Captain Singy (another pirate) catching fighting albacore and throwing them back. And we actually saw a Kennedy, Teddy Jr, speeding down a backstreet on a Vespa without a helmet, a lawbreaker still, even past 60.
FOOTNOTE: A lot has been written about the untimely demise of Jimmy Buffett, the poet of the common man of my generation. Although he wrote the soundtrack of mine and many other lives (Changes of Latitude is the requested see-off song in my will) I’ll always regret missing him live by a whisker on two occasions. The first was in 1986 when Jimmy did an unannounced warm-up set at Moby Dick’s at Whale Beach while I was away on an assignment. My wife and her friends sucked on margaritas and danced the night away just a few feet away from my hero. The second was in 2014 when in Noosa I learned that Jimmy would take to the beach stage at the Quiksilver Pro at Snapper Rocks in less than an hour, meaning I had to miss another memorable impromptu concert, seen in this shot with Jimmy supported by Kelly Slater and Steph Gilmore. Vale Mr Buffett, a life well lived.
