The love of boatracing, the tradition, the boats themselves and the rules of the race are unique to the island of Anguilla.



Boatracing is Anguilla’s national pastime and national passion, each boat with its fans, each captain and crew with its strategy, and each contested finish with its arguments.

As a spectator, there is no other sight that compares to the traditional schooners taking leave of the shore on the bright turquoise water. Oversized white sails like giant wings against the blue. With a formal heritage that harkens back to the early 1900’s, boat racing is both an event and a tradition – as alive today as ever.

A century ago, when the failure of an Anguillian plantation economy was apparent and economic conditions became increasingly severe, the men folk of Anguilla took to the sea for employment on neighboring islands, in particular the cane-plantation rich Dominican Republic. On the return, trips home became fierce competitions in speed. Schooners would battle the weather, the sea and each other to Road Bay for the glory of being the first to arrive home.

In the 1930’s a race of historic proportions took place. The Warspite and the Ismay, two of Anguilla’s most famous schooners, were returning from the D.R. along with several other boats bound from home. On board between the fleet, three to four hundred men, all hungry for the shores of their home.

One Sunday morning, after five days of hard sailing, the schooners were sighted just west of Dog Island, racing toward Road Bay. All the while, church was in session at Bethel Methodist atop of the hill that surrounds Road Bay. As the boats came “hard lee,” tacking away from each other just to the leeward side of Dowling Shoal near Sandy Island, the excitement of the parishioners watching from the church windows became unbearable. Eventually everyone, including the Minister, left their sermon to cheer on their boats from the brow of the hill, leaving the church empty. So began the spectator sport that accompanies boat racing.

The Warspite, Anguilla’s most famous ship. 75 feet long, built in 1902.
Photo: The Anguilla Archeological and Historical Society

Today, boats are still built by hand but are now built using the WEST (wood epoxy saturated) technique introduced by David Carty, rather than carved from the white cedar trees. Size determines whether they are A, B or C class. Class A is the largest and most popular, able to carry 14 men with hundreds of pounds of ballast.

Races are held at various times throughout the spring and summer, beginning around Easter week and culminating in the Champion of Champions, a round-the-island race held in August at the end of Boat Racing Week. Landracers, as the enthusiastic spectators are now called, line the beaches, roads and hilltops to cheer on their favorite boat.

Boat racing events are always accompanied by barbecues, music and dancing – these are “don’t miss” island events that are exciting, beautiful and cultural.

The big 50: Anguilla Day Boat race 2017
Photo: Rudy Webster

Check out David Carty’s documentary Nuttin’ Bafflin’, to learn more about Anguilla’s sailing and boat racing traditions.

And you can view Anguilla’s boat racing calendar of events here.



Anguilla’s thriving tennis culture is due in no small measure to the Anguilla Tennis Academy (ATA), which has been providing tennis service to the island of Anguilla as well as other neighboring countries since 1966. The ATA is a non-profit grassroots program with a mission to empower young people by using tennis as a vehicle for social transformation.

Anguilla Tennins Academy Summer Camp
Photo: The Anguilla Tennis Academy

Founder Mitchelle Lake, an Anguillian tennis star and successful entrepreneur, was determined to not only expose Anguilla’s youth, regardless of economic status, to the lifelong sport of tennis, but also to facilitate educational opportunities, as he was himself the beneficiary of a tennis scholarship.

Over its 21 years of existence, the Anguilla Tennis Academy has helped teach tennis to more than 4,000 kids aged 5 to 17, and some of its most elite athletes have gone on to win athletic scholarships at American universities.

The state of the art tennis facility now hosts the island’s premier tennis event in November, the Anguilla Cup, offering locals and visitors alike the opportunity to enjoy a week of world-class tennis.

Anguilla’s state of the art tennis facility

The Ronald Webster Park, located in The Valley, is home to two public tennis courts.



Competitive road biking is a big sport on the island as fairly flat terrain, quiet side roads and one main road make it easy to cycle around. The eastern end of the island in particular, being quieter and less developed, offers high vantage point views and amazing ocean views.

In July each year the Anguilla Cycling Association ( hosts the John T. Memorial Cycling Race, which is one of the Caribbean’s biggest cycling events.

Cyclists at the Annual John T Memorial Race 2017
Photo: Anguilla Amateur Cycling Association

Road and Mountain Bikes are available for rental from most hotels and local outfitters.



The game of Dominoes is a Caribbean passion, and Anguilla is no exception. The game can be played anywhere, often out on the street in the evening or under a spreading mango or tamarind tree with a tot of rum or a beer. The slam of the tiles hitting the table is a familiar sound, and has even inspired artists.

View Anguilla Art: Domino Tones 4

Though most definitely a social event, Dominoes is also played competitively; the Anguilla Domino Team competes in the World Council of Dominoes tournaments played bi-annually across the region.

Locals playing Dominoes