One of Florida’s most iconic sailing institutions is celebrating a milestone that has been four decades in the making. On Saturday, Aug. 2, St. Augustine Sailing will mark its 40th anniversary with an all-day celebration, complete with dockside festivities, treasure hunt sails, live music and a special look back at the people who turned a dream into a legacy.
From its humble beginnings in 1985 as a small sailing school and brokerage, to its current incarnation under the leadership of Chuck and Rose Ann Points, St. Augustine Sailing has become a vital part of the city’s waterfront identity and St. Augustine’s tourism.
“This isn’t just a celebration of 40 years of business,” says co-owner Rose Ann Points. “It’s a tribute to the legacy of sailing in our community, the families who’ve come through our docks and the thousands of people who discovered the magic of the wind and sea with us. We look forward to sailing these waters for many more years to come.”
St. Augustine Sailing was founded in 1985 by Doug Crane, a local boating icon who dreamed of connecting yacht sales with hands-on education.
Since its inception, each owner has added their own unique touch. Father-son duo James and Adam Royse began offering public charters. Alan Bossenger forged a partnership with the American Sailing Association (ASA) and introduced SailTime, the company’s membership-based sailing club.
The Pointses took over ownership of St. Augustine Sailing in February 2018 and have continued to elevate the sailing experience. They have increased the ASA certification programs to more than 500 students annually, with many traveling nationally to learn; launched their popular Crew & Women on the Water (WOW!) programs; and added luxury private charters with onboard chefs, elopements, corporate team-building events and much more.
“This company isn't just about sailing; it's about people,” said Chuck Points, co-owner of St. Augustine Sailing Enterprises. “It's about creating something meaningful for our crew, our clients and our community.”
To celebrate its 40th anniversary on Aug. 2, St. Augustine Sailing is hosting a mix of sailing and shoreside fun, including:
For more information, go to sta-sail.com.
