On the turquoise waters of Anguilla, there's a heartbeat older than the resorts and more enduring than the trade winds: the thrilling pulse of boat racing. This isn't just a sport—it’s the national pastime, a deep-rooted tradition woven into the cultural and historical fabric of the island. A Legacy Born from Necessity Long before boat racing became an island-wide celebration, it was born of practicality. Anguillians were master boatbuilders and seafarers by necessity. In the early 20th century, small wooden sloops crafted by hand carried men to nearby islands like St. Thomas and St. Kitts in search of work. These same vessels would later become the foundation for a proud competitive tradition. When these men returned home, they began racing their boats for sport—often with bragging rights and a bottle of rum on the line. Over the decades, the pastime evolved into a national obsession, one that defines Anguilla's identity as fiercely as its beaches and its cuisine. More Than a Race To the uninitiated, a boat race might seem like a simple contest of speed. But in Anguilla, it's something closer to theater. Each race day is a full island affair—villagers stake out the best vantage points, music spills into the streets, and bars run dry by sunset. Crew members train with the intensity of elite athletes and boats are backed by passionate sponsors, sometimes entire villages. Each boat has its loyal following, its own color, name, and mythology. There are heroes and rivalries, bitter defeats and legendary comebacks. The races are often marked by cheering from the shoreline and the high-pitched whistles of fishing boats following close behind, turning the sea into a stadium. Race Days to Watch The racing season kicks off around Easter and continues through Carnival in August, with several key races throughout the calendar. The August Monday boat race—held during the island’s biggest summer festival—is the crown jewel, drawing crowds from across the region. Other notable events include the Whit Monday Regatta, Queen’s Birthday Race, and Champ of Champs, each a high-stakes, high-energy spectacle filled with pageantry, party, and national pride. Where to Experience It If you're visiting Anguilla during race season, check local listings and head to Sandy Ground, Meads Bay, or Island Harbour—depending on where the race is being held. Join a crowd of passionate spectators, grab a drink from a roadside stand, and experience this living tradition for yourself. You’ll walk away with more than just sun on your shoulders. You’ll carry a little of Anguilla’s soul. Anguilla Day Premier’s Cup - May 30th, 2025 Light & Peace 2. Real Deal 3. De Wizard Early May - De Wizard captured a major early-season win at Sandy Ground, earning 13 points in the A-Class rankings—followed by Real Deal and Light & Peace.