Offshore Sailing School
Travel ArrangementsFlorida, United States11-50 Employees
Offshore Sailing School is a Sarasota, Florida-based provider of sailing education within the travel arrangements sector. Founded in 1964, it emphasizes hands-on instruction, safety, and the idea that sailing is both a skill and a mindset, with a focus on accessibility and eco-conscious operations. The program relies on certified instructors and modern learning systems to offer hands-on training for sailors at all levels and to support ongoing fleet and program modernization. Led by Brian Crotty, the school is expanding its offerings while preserving its heritage. In 2023 it introduced a combined catamaran and monohull cruising course, reflecting diversification of its sailing experiences, and it announced leadership changes including Dana Matthews's promotion to executive vice president and CFO.