Anguilla is legendary not just for its exclusivity and world-class resorts – but also for its stellar sailing scene. In fact, sailing is a major defining characteristic of island, even moreso than the rest of the Caribbean. The deep and rich history extends back to the original inhabitants of the island, the Taino and Arawak people who’ve called Anguilla home for thousands of years. Long before pirate ships and British colonialism, the natives were sailing the waters with fishing as the goal but freedom and pleasure as the benefit.
The earliest historic reference to proper sailing, as separate to the locally constructed fishing boats, happened during the Napoleonic Wars at what is known as the Battle of Anguilla in 1796. This battle was a doozy, with French forces from St. Martin sailing in two frigates for an attack on what is now known as Rendezvous Bay. The British troops in Anguilla fought back hard and the scrap tumbled across the island. After a ship called for help, the French eventually surrendered to the Anguillian forces. Things didn’t turn out so well for the island, however, as it received an devastating amount of damage. In fact, due to the battle destroying the majority of plantations, the industrial agriculture economy basically collapsed shortly after. The carnage didn’t end there though, as the British-Anguillian forces massacred their French prisoners out of retaliation for the damage caused by the invaders. Harsh.
(It’s of note to mention that the ship that came to Anguilla’s rescue was called the Lapwing, which is now a favored name among Anguilla boats today – especially police force boats – and its original design was the forerunner for the modern racing boats).
In the decades that followed, the plantations were nearly completely eliminated yet subsistence farmers on the island still grew crops. They grew corn, pigeon peas, and other staples and the surplus of yields was shipped overseas in another aspect of Anguilla’s sailing history. However, being of a naturally arid climate, crops didn’t do too well and the locals turned to the old faithful maritime occupations. Fishermen, shipwrights, and traders flourished. After the American Revolution the USA banned trade with the British Colonies in the Caribbean like Anguilla so Canada stepped up to fill the gap. Schooners from Nova Scotia ran the route exchanging Canadian fish and timber with West Indian sugar, rum, molasses, and salt. Like Turks and Caicos, Anguilla was a major salt producer with its 270 acres of salt ponds perfect for raking the white gold.
Due to the presence of schooners and the cash flowing in from international trade, Anguilla was able to expand their sailing with cutting edge technology and techniques. By the start of the 20th century, approximately 4,000 Anguillians owned and operated a trading sloop or schooner, shipping for merchants from the wealthier islands. Anguilla had become a land of expert sailers.
The fishing ships were about 20 feet long and sailed in convoys of three or four boats. They’d embark before dawn to catch grouper, grunt, snapper, and hammerhead sharks. Lacking refrigeration, the early fisherman would have to return by midday to quickly sell their catch. The technologically imposed time limit led to the boats racing home. These impromptu competitions became the foundation for the modern Anguilla sailing races that are so well known today.
To supplement their income, many Anguillian fisherman were also smugglers by night, shipping contraband in the cover of darkness to avoid paying the exorbitant duties. This fired up an entire black market industry shipping rum, flour, rice and sugar to neighbouring islands beyond the reach of the tax-man. In order to smuggle more efficiently, stealthy racing ships were built to be quick and maneuverable. They had collapsable rigging to drop the sails at dawn to avoid detection by authorities and outwit the Revenue Officers. The smuggling boat has since evolved into the sloops used in modern racing.
Which brings us to the regattas. Anguilla hosts sailing regattas on national holidays, attracting locally designed and constructed boats to compete in these major events. One big difference between international sailing rules and those of the Anguilla regattas is the rule to right of way. Instead there is but one rule: the hard lee – which the captains call for to make both boats ‘tack’ regardless of advantage, instead of just politely giving way to the boat on the starboard side.
August Week is a huge time for racing in Anguilla, commemorating the Emancipation Act of 1834 that freed the slaves under British control. August Monday has been a big festival since that time with fishing villages competing against each other in sailing races. The annual Anguilla Regatta is held in May and features an assortment of races from 15 to 22 miles in length. It’s an exciting time not just for the racers but for the spectators, as the whole island gets pumping, especially in Sandy Ground. It’s the perfect opportunity for a party, and all the beach bars will be cranking tunes and serving drinks and people will be ‘mashing sand’ (as they call dancing in the Caribbean) and having a blast.
If you’re looking for a great time to visit Anguilla, we strongly recommend visiting during a sailing race. It’s the perfect way to soak up some authentic Anguillian culture. Raise your own proverbial sails, as it were, and may the wind be always at your back.