The love of boat race, the tradition, the boats themselves and the rules are unique to the island of Anguilla.  As a sporting event, boat race is surpassed by no other sport, each boat with its fans, each captain and crew with its strategy and each finish with its arguments.

2016 Calendar of Boat Racing & Yachting Events


Date Event Location Class
March 2 Ronald Webster Day Sandy Ground to Island Harbour B Class
March 26 Easter Saturday Island Harbour B Class
March 27 Easter Sunday Island Harbour A Class
March 28 Easter Monday Sandy Ground to Sandy Hill A Class
May 6-8 Anguilla Regatta Sandy Ground
May 12 Regatta Race Sandy Ground B Class
May 16 Whit Monday Sandy Ground A Class
May 30 Anguilla Day Round the Island Race Sandy Ground A Class
June 13 Queens’s Birthday Sandy Ground A Class
June 19 Father’s Day Sandy Ground A Class
July 14 Bastille Day Marigot SXM B Class
July 24 SXM Fete Grand Case B Class
July 24 Peter Perkins Sandy Ground A Class
Anguilla Summer Festival Events
July 31 Heineken Warm-Up Sandy Ground A&B Class
August 1 Caribbean Beach Party August Monday Sandy Ground A&B Class
August 2 August Tuesday Sandy Ground to Island Harbour A Class
August 3 August Wednesday Sandy Ground to
Blowing Point & Back
A Class
August 4 ATB August Thursday Meads Bay A&B Class
August 7 Champion of Champions Sandy Ground A&B Class


As a spectator, there is no other sight in all of sports 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 race is both an event and a tradition – as alive today as ever.

Centuries 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 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 arriving home first.

In the 1930’s a race of historic proportions was had.  The Warspite and the Ismay, two of Anguilla’s most famous schooners were on return 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 race.

In 1918, according to Sir Emile Gumbs, the first organized boat race occurred as part of the celebrations marking the end of World War I.  The race, which was held in Crocus Bay, was open to all fishing boats and was won by “Repel” a boat built and owned Joe Hodge of Long Bay.  However, the first race and its winner are still disputed on Anguilla to this day.  What is not up for dispute is the passion for this sport and its continued tradition.

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 and 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 Champion race held in August at the end of Boatracing week.  Landracers, as the enthusiastic spectators are now called, line the beaches roads and hilltops to root their favorite boat in.

Boatrace is accompanied by barbecues, music and dancing, and is a “don’t miss” island event that is exciting, beautiful and cultural.

Follow us on


Nuttin Bafflin

Written by Anguilla's best-known boat builder, "Nuttin Bafflin" is a filled with the stories and anecdotes of our our island's boat racing history.