Rum-racing Caribbean-style

May 15, 2017 General Interest

Sailing regattas are usually fairly dignified events with an established set of rules governing the proceedings. But in parts of the Caribbean things are run very differently, writes Lindsay Wright, who also took the photos.


Most months the Caribbean island of Anguilla lies sweltering in the tropical sun. Gaunt and thorny scrub covers much of the 950km2 landscape, tourists bake on the beaches and a garland of turquoise sea drapes around the coral-bound coastline.

But August is the beginning of the boat racing season. Sleek and colourful hulls are hauled from sheds to have their winter covers stripped away. They are winched onto trucks then joined by crowds of grinning locals and taken to Sandy Ground at Road Bay.

An infectious zeal spreads round the island – the boat races are coming. Boat race season is party time, when Anguilla comes alive. People pick their favourite boats and roadside discussions develop into heated debates about which boat, or captain, will take the season.


Some boats have been reshaped during the off-season and the alterations are hotly discussed. Top captains attract more adulation than Richie McCaw at a hen party and Anguilla’s 8,500 or so people radiate a fervour which makes a crowd of America’s Cup spectators look like a Presbyterian prayer meeting.

Here there’s none of the black blow-fly outfits worn by Team New Zealand – crews wear worn T-shirts and shorts. But there is passion: quiet, focussed passion on the boats and raucous party passion on the beaches.

Boat racing has a long history on the little British dependency in the eastern Caribbean. Pirates once used Anguilla as a base to pick off passing Spanish treasure ships – racing for their lives from the Royal Navy or other enforcement agencies. So boat racing has a long and colourful history on this tiny Caribbean island.

Most of the populace arrived from Africa in slave ships to serve on the island’s sugar plantations. The plantation economy was doomed by Anguilla’s arid climate, poor soil and devastation caused by the hurricanes which regularly track through the area.

The Emancipation Act of August 1, 1834 freed all slaves under British control and its enactment is still celebrated with public holidays throughout the former British Caribbean islands.

The freshly-freed slave population took to fishing and subsistence farming for a living. Fishing boats became Anguilla’s first racing boats. Measuring between 17-feet (5.2m) and 20-feet (6.1m) with 40-foot (7.6m) masts made from local soursop wood, the boats raced home each day to unload their catch before it went off in the warm tropical air.

Fishing schooners from the Canadian Maritimes, Newfoundland and Nova Scotia soon cottoned onto the area as a source of the salt they needed to preserve their catch and began to arrive to trade fish for salt, sugar, rum and molasses.


A Canadian government policy of replacing the big schooners every 10 years meant many came up for sale and were snapped up by Anguilla men who became famous for their ventures freighting and smuggling around the Caribbean and North America. Many cargoes of illicit spirits were offloaded into US vessels from Anguilla schooners during Prohibition.

With agriculture work hard to come by, many menfolk went to work cane-cutting on the Dominican Republic plantations, sailing in the schooners Ismay and Warspite. At the end of the season the schooners and their cargoes of homebound husbands, fathers and lovers, raced home. Every man aboard took part in weight distribution and deck work during the four-day passage.

There are accounts of churches emptying out in mid-service when the congregations sidled outside to watch the schooners beating, tack for tack, into Road Bay.

Anguilla’s subsistence farmers couldn’t afford to pay labour to help till the ground and held “jollifications” where friends and neighbours gathered to help out and were paid in rum. Duty and
taxes imposed by their British overlords meant that a demijohn of rum – which could be bought for three shillings in the nearby French island of St Martin – cost 20 shillings in Anguilla.

And that’s where Anguilla’s sloop racing really came into its own. The design brief called for a vessel that could sail to St Martin overnight, load up with liquor and trade goods, and be back on its home mooring with sails furled and mast struck, before the excise men came snooping around at dawn the next day.

These days the boats are built using WEST system epoxy and come in three classes: A, B and C, depending on size. The A class boats, stars of the fleet, are required to be 28-feet (8.53m) or less LOA, and carry a 40-foot (12.2m) mast. Beam or draught are open and the boats carry 2,272kg of ballast in
sand bags and lead pigs. Additional ballast is supplied by the crew – about 14-22 per boat.


All this is powered by a huge mainsail and small jib. Over-exuberant operation – or sudden wind gusts – can cause the boats to fill with water and sink. Divers normally remove the ballast so the wooden hull can float to the surface for salvage.

Captains will pick larger crew members on windy days and skinny ones in the light, but crew are often called upon to abandon ship on the last leg of a race. This is done by crouching on the transom and pushing hard with your legs as you leave the vessel.

Any of the armada of boats which follow the fleet to cheer on their favourites (and ridicule the opposition) collect “jumpers” from the water and thrust a tumbler of rum in their hands.

Otherwise the racing boats carry only what they need to win: buckets, bailer and a communal jug of fresh water.

The boats also have a manager and fan club who pack onto the back of trucks and follow the fleet around the coast, from headland to headland, checking on progress with binoculars and loudly debating tactics or weather.

Meanwhile, out on the water, Anguilla sloop-racing rules apply. If two boats are on a collision course the skippers yell “hard a lee” and are required to tack – regardless of whether or not they gain ground during the manoeuvre.

It becomes a game of chicken; skipper and tactician hunched at the stern anxiously eyeing their opponent. “Show no fear men,” is the traditional call and every breath is baited until the sloops sweep past each other with centimetres to spare.


The first boat to arrive at a mark chooses which side to pass it on and the rest of the fleet must follow suit except for the last-placed boat which can pass it either way.

Meanwhile a party is raging on the beach at Sandy Ground. Golden tourist girls in barely enough bikini
cradle rum punches and saunter through the golden sand, reggae beats from the beach bars and scores of binoculars glint in the sun while the big white spread of sail races towards the beach.

The finish buoy is anchored in the shallows just off the beach and a crewman must snatch the small pennant fluttering from it to claim first place for his craft.

A roar erupts from the onlookers, crews hike out with their heads near skimming the sea, mainsheet blocks squeal and just when it seems the boat will carve a furrow through the crowd, the captain downs the helm. The crew stay alee and death roll the boat to windward while a black hand darts out and grabs the flag.

De Tree does it again, with Tsunami just a boat length behind her.