The Virgin Islands Optimist sailing team competed in the St Thomas Yacht Club's Fall Regatta on October 9-10, 2026. The team consisted of Piper Bailey, Bobby Hensley, Sean Stacey, and Jervis Tucker-Davis.

Sean Stacey won one race and placed 3rd overall in the Green Fleet, while Jervis Tucker-Davis placed 5th. In the Championship Fleet, Bobby Hensley achieved 4th place three times, and Piper Bailey finished 7th overall.

The regatta provided valuable experience for the young sailors.