Barbados Sailing Week 2026

The Caribbean racing season begins in mid-January with the Round Barbados Sailing Week. There is an electric party vibe throughout the island as the regatta coincides with the celebration of the birthday of Barbados’ first Prime Minister and co-founder of the Barbados Cruising Club. Not only that, but Errol Walton Barrow is also known as the ‘Father of the Nation’, so it’s easy to see why Barbadians have much to celebrate at this time of year.

Although the first official race of this week-long regatta began in 1936, the tradition of racing around the island dates back much further. Way back in the 19th century, when prizes for cargo arriving before rivals’ ships could command a massive premium, traders would earn bragging rights for having the fastest schooner into port. However, there was also a consolation prize for the slowest ship. This prize became so coveted that they had to stop awarding it after two ships deliberately loitered at sea for days to win. The prize? An entire barrel of Mount Gay Rum—hardly surprising they were tempted!

These days, a new tradition rewards anyone who breaks one of the 20 current records with their skipper’s weight in rum. As if anyone needed an excuse to overindulge during the festive season, this race is certainly not one for a skinny skipper!

This is a unique regatta as there isn’t a marina near the yacht club, meaning we rely on our dinghy to shuttle us back and forth from the mooring ball.

With three training days, two coastal racing events, the prominent Mount Gay Round Barbados Race, and lively after-race parties—plus the incentive of your skipper’s weight in rum—what are you waiting for?