Anguilla Experience, Caribbean Events

Sailing in Anguilla – The Undisputed Fever for Boat Racing

sailing in anguilla

Forget football, baseball, or basketball, the national sport of this exclusive and idyllic island is much more glamorous and adventurous.  Sun, wind, sea, and sails. That’s right sailing is the national sport of the Caribbean island of Anguilla.

All 35 square miles of Anguilla is completely surrounded by sparkling turquoise water. It’s no wonder the national sport became sailing, with little land mass and plenty of sea, seems like the obvious choice!

Except, sailing became the national sport for a less-than-obvious reason, a reason that is both fascinating, and exciting to hear.

It all started with sugar….

How Sailing in Anguilla Came to Be a Hot Sport

sailing in anguillaThe year is 1884, and the Dominican Republic is experiencing a slump in sugar prices, resulting in the farmers putting a freeze on the wages, causing a shortage in available local labor.

Anguillians to the rescue. They hopped in their crudely constructed schooners, sailed 450 miles west to the D.R., which took a couple of days.

It may have been a quick trip to the D.R., but it certainly was not a quick trip home. Due to intense winds, conditions were harsh, and the return trip could take up to two weeks. One meal a day, nowhere to sleep other than an exposed deck or ballast rock.

The rush to get home intensified as the journey continued, and once the ships near Anguilla, they began to race.

From that point on, the spirit of the of competition prevailed, and thus sailing became the national sport.

Ok, so that was the quick version, there were many more events between 1884 and now of course, but that’s how it all got started.

It wasn’t until 1940 when the very first August Monday boat race was held – which featured five different types of boats ranging in size.

The rest is history!

As David Carty says in his documentary about the journey of sailing on Anguilla, Nuttin’ Bafflin’:

“Within this island, lapped by the crystal blue-green waters of the Caribbean, lurks a fever for boat racing.”

Yes it’s true, Anguillians have it bad for boat racing.

sailing in anguillaThough the island may be small, it’s love of sailing is fierce. The biggest sailing event of the year takes place during the biggest festival of the year – Carnival. Carnival takes place the first week of August, and though you may be picturing sequins, dancing ladies, and a huge parade, it’s actually the sailboat races that takes the cake for biggest event of Carnival.

August Monday, the longest, and most exciting day of the year on Anguilla. From 5 a.m. through the next morning, Anguillians and visitors alike are celebrating to the fullest potential.

Anguilla boat racing is the lifeblood of the country, and nearly every local is passionately following the race, cheering on a specific boat.

For Anguilla, August Monday is their version of the Super Bowl. The passion and excitement extends way past the locals – vacationers, visitors, and neighboring islands all get swept up in the excitement, it’s impossible not to!

Anguilla plays host to many annual sailboat racing events and August Monday may be the biggest, but there are plenty of other events that keep the sailing spirit strong all year long:

  • Easter Monday Race
  • Anguilla Day – May 30th
  • Queen’s Day Boat Race in June
  • August Thursday (same week as August Monday)
  • Champion of Champions (Sunday following August Thursday)

There’s plenty of racing excitement to be had all year long, and when Anguillians aren’t racing, they’re practicing, preparing, and strategizing for the next race.

It’s truly a magical and exciting time to be on the island, and we highly recommend visiting during one or more racing events. Be sure to plan your trip well in advance, though, because the small island gets booked up quickly! For a private villa, private beach, and unparalleled luxury, seek out accommodations at Cap Juluca Resort, one of Anguilla’s finest.

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