Earlier this week, Caught in Southie featured South Boston native Jane Matthews, who is making waves as the only woman aboard the racing yacht Lynx in the 2026 Newport Bermuda Race. As it turns out, there’s another impressive Southie sailor heading to Bermuda this year, too.

Abby Gwynn, 23, will be the youngest and only woman aboard Starflight, a Swan 48 based out of South Boston, as it competes in the iconic 636-mile ocean race from Newport, Rhode Island, to Bermuda.

Abby’s sailing journey began at just 8 years old through programs at Harry McDonough Sailing Center and South Boston Yacht Club. A graduate of Boston Latin School, where she captained the sailing team, Abby has since participated in numerous races, boat deliveries, and sailing projects while also pursuing a career in nursing.

For the past three years, Abby has served as director of the South Boston Yacht Club Junior Sailing Program, helping young sailors develop their skills and passion for the sport. She is also a member of a Massachusetts Bay Sailing Association committee dedicated to expanding sailing opportunities for youth across the state.

Abby credits both South Boston Yacht Club and Savin Hill Yacht Club for helping her grow as a sailor and connect with the broader sailing community.

Now, she’s preparing to add the Newport Bermuda Race to an already impressive sailing résumé. We wish Abby fair winds and following seas as she takes on this incredible challenge!