St Augustine Sailing Celebrates 40 Years
For four decades, St. Augustine Sailing has been the heartbeat of maritime adventure in St. Augustine, Florida. From our home at Camachee Cove Yacht Harbor, we’ve shared the joy of sailing with countless dreamers, adventurers, and families. As we mark our 40th anniversary, we invite you to join us for our 40 for 40 Celebration on Aug. 2, 2025 — a day of sails, smiles, and stories that honor our past and set the course for our future. Below, we dive into the event details and trace the remarkable journey of St. Augustine Sailing, from its founding to its vibrant present, through the visionaries who made it all possible.
40 for 40 Celebration: Join Us on Aug 2nd
We’re pulling out all the stops to celebrate 40 years of sailing excellence! On August 2, 2025, at Camachee Cove Yacht Harbor, we’re hosting a day packed with adventure and festivity. Here’s what’s in store:
- 40% Off Private Sails: Book any private sail and enjoy a 40% discount, making it the perfect time to experience luxury on the water.
- Treasure Hunt Sails: Set sail on one of two thrilling treasure hunt sails for just $40 per person—a nod to our adventurous spirit.
- Themed Photo Booth: Capture the moment with fun, nautical-themed photos to commemorate the day.
- Evening BBQ & Celebration: Starting at 6:30 p.m., join us for a delicious barbecue with beverages, live music, and our 40th anniversary cake, all for $40 per person.
Don’t miss this chance to celebrate with us! Book your spot now online or call (904) 829-0648. This event is more than a party — it’s a tribute to our community, our passion, and the sea that connects us all.
Doug Crane, Sr.: The Founder Who Set the Course
In 1984, Doug Crane, Sr. launched St. Augustine Sailing with a vision as vast as the ocean itself. A seasoned mariner, Doug honed his expertise at Beach Marine in Jacksonville Beach, eventually rising to President. His experience in boat sales and instruction fueled his dream to create a full-circle sailing experience in St. Augustine. As a Pearson sailboat dealer, Doug didn’t just sell boats — he built a community by offering lessons and charters that sparked a lifelong love for sailing.
Doug’s impact extended beyond the business. As President of the Jacksonville Marine Association and a Commissioner of the Florida Inland Navigation District, he championed improved access to Florida’s waterways. His legacy endures in the Douglas C. Crane Boat Ramp, a fitting tribute to a man who made sailing accessible to all. Doug’s son, Doug Crane, Jr., reflects fondly: “My father’s goal was simple — to make a life on the water possible for everyone.” That vision remains the wind in our sails.
James & Adam Royce: A Father-Son Bond Strengthen by the Sea
The next chapter of St. Augustine Sailing began when James Royse acquired the company, driven by a desire to share his passion for sailing with his son, Adam. Focusing on charters and the sailing school, they upheld the company’s reputation for quality instruction and warm, welcoming service. For James and Adam, running the business was as much about building memories as it was about sailing.
Adam recalls, “We weren’t just teaching sailing. We were living it — together.” Their father-son partnership strengthened not only their bond but also the company’s foundation, ensuring that St. Augustine Sailing remained a beacon for aspiring sailors. Their era set the stage for the professionalization and growth that would follow, keeping Doug’s legacy alive while charting new waters.
Alan & Becky Bossenger: Professionalized Sailing
When Alan Bossenger retired from his corporate career, he sought a new adventure — one that led him to St. Augustine Sailing. Drawn to the company’s strong reputation and values, Alan immersed himself in its operations, bringing a strategic mindset and a deep love for the sea. Alongside Captain Chuck Points, he ensured all skippers were licensed as U.S.C.G. captains, elevating the company’s professionalism.
A pivotal moment came when Alan transformed the sailing school into a certified American Sailing Association (ASA) training center, a milestone that solidified St. Augustine Sailing’s commitment to excellence. In 2006, Alan and his wife, Becky, expanded access further by acquiring the SailTime Northeast Florida franchise, allowing locals to sail regularly without owning a boat. Their contributions laid the groundwork for a more accessible and professional sailing culture, setting a high standard for the future.
Chuck & Rose Ann Points: Passion, Purpose & Family
In 2018, Chuck and Rose Ann Points took the helm, bringing a shared passion and a family-centered vision to St. Augustine Sailing. Rose Ann’s maritime roots run deep, having lived aboard a Morgan Out Island Ketch with her children for 13 years, sailing from Maryland to the Caribbean. Chuck, a lifelong sailor since age 15, has navigated waters from Lake Superior to the South China Sea, holding a USCG Masters 100 GT Captain License and earning ASA Outstanding Instructor awards.
Their journey began in 2012, when the newly married couple sought a new path together. Rose Ann’s boating experience and Chuck’s suggestion—“Well, you know boats”—sparked their venture into yacht sales through All Points Yacht Sales. When Alan suggested they buy St. Augustine Sailing, they embraced the challenge, uniting their family in the mission. Rose Ann’s children—Derk (photographer), Toste (guest services), and Lance (maintenance), along with their spouses, Pablo (dock hand) and Amberle (the ultimate “Girl Friday” who helps with everything) all joined the team, turning St Augustine Sailing into a truly all hands-on deck family affair.
Under their leadership, St. Augustine Sailing flourished with innovations:
- Crew Program (2020): Keeps students engaged with ongoing skill-building.
- Women on the Water (2022): “WOW!” empowers women to sail with confidence.
- High Tea Adventure: A heartfelt sail serving tea from heirloom teapots, honoring Rose Ann’s mother, Dora. “Through tea, I share a piece of my mother’s heart,” Rose Ann says.
Rose Ann’s philosophy — “I can’t do everything, and I’m not meant to. That’s why we build a team who leads with heart” — defines their approach. Today, the company offers luxury charters, ASA-certified lessons, weddings, corporate outings, and culinary sails, all delivered by U.S.C.G.-licensed captains and a passionate crew.
What Makes Us Unique
At St. Augustine Sailing, we pride ourselves on offering luxury at an affordable price. Our fleet is the newest and cleanest on the water. Our fanatical commitment to customer service ensures every guest leaves with magical memories. Whether through our SailTime membership, All Points Yacht Sales, or specialty sails like the High Tea Adventure, we tailor every experience to your dreams.
Rose Ann sums it up: “It’s about helping people make their sailing goals a reality.” For Chuck, it’s simpler: “You’re out sailing, and the people are great.” Join us to discover why St. Augustine Sailing is the premier choice for on-water adventures in Florida.
A Heartfelt Thanks
As we celebrate 40 years, we reflect on a journey built on passion, community, and the sea. To our team, students, and guests: your support has made these 40 years unforgettable. As we look to the future, we remain committed to sharing the sailing lifestyle through our newest yachts, exceptional service, and customized experiences that create lifetime memories. The wind is steady, the horizon is bright, and the adventure continues.
Our 40 for 40 Celebration on Aug. 2 is our way of saying thank you — to our founders, our team, our community, and you, our guests. Join us for discounted sails, treasure hunts, and summer BBQ eats at Camachee Cove Yacht Harbor. Book today or call (904) 829-0648.
Here’s to 40 more years of wind, waves, and unforgettable adventures!
For more information and to stay updated, visit www.sta-sail.com and follow them on social media @StAugustineSailing.
