A Brief History of Sail

A Brief History of Sail


“Come, give me a hand,” said Deb, the first mate, looking in the direction of a few passengers. “We’re going to sweat it up.” The ‘it’ was the mainsail, which needed hoisting. It was clear that this wasn’t a one-man (or woman) job, and looked backbreaking.

We were aboard Tradition, an old, gaff-rigged West Indian sloop – for us non-mariners, she’s a single-masted classic sailboat. We were about to head out on a sailing excursion from Sandy Ground in Anguilla. This was to be my first sail, which is curious, since I live on an island teeming with boats. I’d been on motorboats plenty of times, but sailing is different.

A few weeks before, I’d seen Nuttin Bafflin, local boat-builder David Carty’s ode to sail. It’s billed in some quarters as a history of the national sport, boat racing. I prefer to think of it as a history of Anguilla. It was captivating. I’d never sailed before, but I knew I wanted the experience, and Tradition was the perfect opportunity to pop that particular cherry. Built in Carriacou, Grenada in the late 1970s, she’s reminiscent of the Anguillian sailboats of old, with a long, low keel running the entire length of the boat.

Like most other things Anguillian, the choice to use a low keel in Anguillian boat-building was born out of necessity. With no boat lifts or slips or any other kind of protected mooring, it was necessary to haul boats by hand, on rollers, onto the shore for their protection.

Vrooom! The engine sputters to life. Wait, it has an engine? I thought this was supposed to be a sailing trip. Laurie, our captain, explained that this was the norm on classic working auxiliary vessels. The engine would allow us to manoeuvre through the tight spaces in the bay. Fair enough, I thought, but somehow it felt like cheating.

The sail was up, the engines shut off, and we started bobbing and rolling with the sea. It was quiet, and only the sound of waves lapped at the side of the vessel. The wind feels good on the face. I wandered through my thoughts, lost. This could well have passed for a scene from a century before, when Anguillians would travel the high seas in search of opportunity.

Anguilla’s sailing history is intriguing. The decline of the plantation economy in the 19th century forced Anguillians to develop a greater connection to the sea as a means of survival. They made of the most of the challenge, becoming expert shipwrights, boat-builders and seafarers in the process. Salt, then phosphorus, catalysed a new era of trade with Nova Scotia and New England, bringing not only a much-needed economic lift but also better shipping technology and expertise. By the time of the early 20th-century rise of the sugar industry in the Dominican Republic, Anguillian shipwrights were building vessels, large and small, capable of navigating the region, bringing trade and survival to the tiny island.

We head out of Sandy Ground around 5pm for what the captain tells us will be a “3 hour tour.”…wait, what? My brain starts doing the thing that brains do when trying to reconcile old memories to present experiences. In this case, it was a popular 60’s TV show theme song. A three-hour tour…a three-hour to…

“Coming about!” roars the captain, waking me from my daydream. I then take a second to survey our crew: I see Laurie Gumbs, our seasoned captain, with his sun-bleached blonde hair and sun-tanned dark skin. Laurie hails from a nautical lineage – before becoming Chief Minister of Anguilla, his father, Sir Emile, was captain of the famous schooner Warspite and owner of the smaller Sagaboy, a racing boat.

Deborah Vos, first mate, has circumnavigated the Atlantic Ocean. In fact, that voyage had been her first major sailing experience: one day, the Alberta, Canada native hopped aboard the Nova Scotian tall ship Picton Castle and stayed there for nine months, living with a crew of trainers and trainee sailors. Talk about jumping in at the deep end. Finally, there was Brennan Gumbs (no relation), the deckhand. A quiet, calm exterior belies a knowledgeable sailor who already has a few years of sailing under his belt.

I felt comforted. This was no S.S. Minnow; our crew had serious pedigree.

Squeeaaal! A shrieking shatters the silence. A passenger had just made use of the “head”, the boat’s lavatory. The sound was a result of a misbehaving plumbing vent, I was told. In any event, we were fortunate – the men who set off to cut sugar cane in the Dominican Republic had no such luxuries. Hanging overboard sufficed.

In those days, men got by on a single meal per day. When we dropped anchor in Little Bay and settled in for some hors d’oeuvres, we had an absolutely lavish spread in front of us: brie, goat cheese, strawberries, wine. This was positively regal.


The night sky was beautiful, which meant Deb couldn’t help but be romantically nostalgic about her circumnavigation, where, during her regular night watches, she felt like a part of the sky. It was easy to understand, with clear night sky above us, I could see all the constellations I knew how to name.

Our dining now finished, we raised anchor and start making our way back. It was a much quicker journey, as the wind was at our backs.

“Are we there yet?” asks one passenger. Somehow, I doubt he’d have lasted the trip back from Santo Domingo. The journey over would have been a nice, snappy affair – a couple of days sailing downwind. The trip back could last up to two weeks if the wind was poor. To help with the monotony, passengers would bet on which boat would return first. Those on shore would also eagerly await the men’s return, ready with wagers of their own. This led to fierce competition between boats as dozens of Anguillians returned after the sugar harvest. The birth of modern Anguilla’s boat racing is credited to these races.

One legendary race in the 1930s was between two of the most famous schooners: the Ismay and the Warpsite. The race was so heated that people in church on that Sunday morning abandoned the sermon to cheer the men home. The Ismay won, not that it mattered, because the seeds of the national sport had been sown.

The rise of outboard motors led to the slow death of sailing for necessity. Now, we sail for fun, and sport. Local holiday boat-racing helps keep the spirit of these pioneers alive. Anguillans still wager on these races, but village pride and bragging rights are what’s at stake. I’m still not fully immersed in it, sadly, but maybe that will change now.

Vrooom! The engine roared and, again, broke the silence. It was dark when we got back, and no crowds of women and children awaited us in Sandy Ground: just the dark silhouettes of other boats. Back on land, I walked with the kind of swagger that only earning your sea legs can provide. I could now boast of being a seafarer.

If motorboats are our way of conquering the ocean, then sailing is our way of showing it respect – it is man connecting with the sea in the most basic and primal manner. Yeah, sailing is different.IMG_6001-1



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