The Gem Trophy memorializes the ideals of long-time club member, the late William Ziegler, III, an accomplished sailor who frequently raced his yacht named GEM at Block Island Race Week with young sailors, some of whom were recruited off the dock on race day. The trophy will be presented to the best yacht with at least 70 percent of its skipper and crew, male or female, younger than 25 years of age. Donated by Steve and Heidi (Ziegler) Benjamin.

2015 - Ranger - Dax Ansley
2017 - Night Moves - Colby Thim
2019 - Summer School - Mudratz Offshore
2021 - Beagle - Willets Meyer
2023 - Mad Blue - MudRatz