Round Barbados Sailing Week

The very beginning of the Caribbean racing season starts from 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 you can probably see why Barbadians have something to celebrate at this time of year.

Although the first official race of this week long regatta began back in 1936, the tradition of racing around the island dates back much further into history. Way, way back in the 19th century where prizes for cargo arriving before rivals’ ships could raise a massive premium, the traders could declare bragging rights for being the fastest schooner into port. There was however, a consolation prize for the slowest ship. This prize was so esteemed that they had to stop handing out a last-to-finish prize after 2 ships loitered at sea for days with the intent of winning. The prize was an entire barrel of Mount Gay Rum so I can certainly understand their motives.

These days, there is a new tradition where if you break any of the 20 current records, then you can win your skipper’s weight in rum. As though anyone needs an excuse to over indulge in the festive season, this race is not one for a skinny skipper!

This is a very unique regatta as there simply isn’t a Marina near the yacht club, therefore we are reliant on our Dinghy to shuttle us back and forth from the mooring ball.

Made up of four training days, four coastal racing day events and after race parties with the incentive of your skipper’s weight in rum, what are you waiting for?

*** Barbados Sailing Week 2025 has been confirmed for Jan 17th – 22nd, however, the exact schedule has yet to be released. We do not believe the dates below will be altered, but please occasionally check this page as we will be updating it as soon as the full official schedule is released.