St. Augustine Sailing Celebrates 40 Years
ST. AUGUSTINE, Florida (July 2, 2025)— One of Florida’s most iconic sailing institutions is celebrating a milestone that has been four decades in the making. On Saturday, August 2nd, St. Augustine Sailing will mark its 40th Anniversary with an all-day celebration, complete with dockside festivities, treasure hunt sails, live music, and a very 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 passionate 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 Rose Ann Points, co-owner of St. Augustine Sailing Enterprises. “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. Chuck and Rose Ann Points took over ownership of St. Augustine Sailing in February of 2018 and have continued to elevate the sailing experience. The Points have increased the ASA certification programs to over 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,” shares Chuck Point, co-owner of St. Augustine Sailing Enterprises. “It's about creating something meaningful for our crew, our clients, and our community."
ABOUT ST. AUGUSTINE SAILING: St. Augustine Sailing Enterprises offers a luxury adventure experience, providing a variety of sailing excursions to suit any occasion and budget. They offer public and private charters that can be customized to create a unique experience. St. Augustine Sailing also offers sailing lessons and membership in SailTime®, a club allowing members to rent a boat at franchises nationwide. Photos may be found here. For more information on their programs, visit sta-sail.com. Follow along on social media @StAugustineSailing
