Oyster describes the Rally as the only fully supported circumnavigation of its kind, and the structure explains why. The route is built around global weather patterns, aiming to keep big passages in the right seasons, then giving crews enough time at each stop to actually enjoy the place rather than rush straight back to sea.
This year’s fleet has a broad spread. Owners represent eight nationalities, including the US, UK, Australia, Canada, and several European countries. The boats range from 50 to 90 feet, with 15 described as new generation Oysters, including multiple 565 and 595 models, plus a flagship Oyster 885.
The support package is a major part of the pitch. Oyster says it helps owners prepare through a training programme developed specifically for the Rally, then backs the fleet on the ground with technical and logistics teams as the voyage unfolds.
Several of the yachts arrived in the Caribbean via the Atlantic Rally for Cruisers. Oyster points to an all Oyster top three in Cruising Class B, with Odisea, Alpenglow and Carina separated by 16 hours on uncorrected time.
A notable addition this time is Oyster’s Owner and Chairman, Richard Hadida, joining the Rally with his family aboard the Oyster 885 Lush. He describes it as a long held ambition, and a chance to experience the world at sailing speed, mile by mile, rather than by air.

With this edition underway and the 2028 Rally already close to full, Oyster’s circumnavigation programme shows no signs of slowing.
















