THIS second Thursday in January is a perfect Florida winter morning, the sort of weather the local chamber of commerce dials up regularly—a light easterly breeze barely ruffling the shallow, pristine waters of Sarasota Bay. Along the beach that fronts the busy Sarasota Sailing Squadron, there is commotion; like every early Thursday morn from September through May, several dozen seasoned gals known as the Luffing Lassies, almost all with their diverse and accomplished working lives in the rearview mirror—and none of whom will be remotely mistaken for college kids—are rigging up their prams, 420s and Sunfish for their weekly fix of sailboat racing. This particular Thursday, however, is somewhat different: It is the running of the 24th Annual Lilly Kaighan Memorial Regatta, so named for the Lassies’ founder, the somewhat…
