A maritime tradition that has become a hallmark of Boston’s summer calendar traces its origins back more than three decades to an unexpected conversation at a holiday gathering. In the late 1980s, then-Massport executive director Dave Davis learned of plans for a 1992 regatta commemorating the 500th anniversary of Christopher Columbus’s voyage. Seeking to involve Boston in the celebration, Davis approached Dusty Rhodes, founder of the event planning company Conventures, to lead the initiative.

Rhodes, whose experience with nautical events was limited, took on the challenge of organizing the city’s participation. While tall ships had previously entered Boston Harbor during the nation’s bicentennial in 1976, this effort marked a new chapter managed solely by Rhodes. Despite encountering considerable obstacles, including internal disputes and public controversy, she succeeded in launching the inaugural Sail Boston in 1992. A contemporary newspaper dubbed her the “unsinkable Dusty Rhodes,” a moniker that has endured throughout her ongoing stewardship of the event.

Last weekend, more than 50 tall ships once again made their way into Boston Harbor for the latest iteration of Sail Boston, a celebration that runs through Thursday. This marks Rhodes’s fifth time directing the event, underscoring her enduring commitment at age 77. Speaking from the event’s command center near Northern Avenue, she emphasized the community’s enthusiasm and the joy the spectacle brings to attendees.

Beyond her personal involvement, Rhodes’s lasting contribution may lie in the organizational framework she has established. The team and infrastructure supporting Sail Boston have been built with an eye toward sustainability, ensuring the event’s continuity well beyond her eventual departure from leadership. While she remains reluctant to speculate on how much longer she will continue at the helm, Rhodes’s impact on Boston’s maritime cultural scene is firmly secured.