- St. Augustine, Florida 32084
- Call us: 904-829-0648
For four decades, St. Augustine Sailing has been helping people cast off their lines, catch the wind, and discover a passion for life on the water. As we mark this incredible milestone, we invite you to celebrate with us—past, present, and future sailors alike. From dockside festivities and special anniversary sails to personal stories from each chapter of our journey, this page is your home base for all things #SailInto40. Explore our calendar of events, watch our four-part video series, and dive deeper into our legacy through the 40th Anniversary blog. Let’s honor the past and sail into the next adventure—together.
EVENT HIGHLIGHTS – SATUDAY, AUGUST 2 ALL DAY
6:30 – 8:30 PM at the docks
Join us for a laid-back dockside BBQ with:
The story of St. Augustine Sailing begins with Doug Crane, Sr., a prominent figure in the Northeast Florida marine industry with a deep passion for sailing and a strong commitment to doing things the right way. Doug came from a powerboat business background, but it was sailing—and the people drawn to it—that truly captured his heart.
As his son, Doug Crane, Jr., recalls in our anniversary video series:
“Dad always had this powerboat business mentality, but he loved sailing more. He loved seeing people out there, enjoying it. People who sail become yachtsmen—they learn boating, and they learn it properly. That’s what he wanted—yachtsmen, not just boaters.”
Doug’s approach to selling boats was refreshingly honest and focused on long-term satisfaction. If someone came to him wanting to buy a sailboat but didn’t seem ready, he wouldn’t push the sale. Instead, he’d suggest they go through sailing instruction first and revisit the decision with confidence.
“I think people really appreciated that about him,” Doug Jr. adds. “He was honest and straightforward—he wanted you to love it and be prepared for it.”
Doug founded St. Augustine Sailing in 1985 as both a sailboat dealership and sailing school—knowing that education was the key to creating lifelong sailors. For him, it wasn’t just about putting people in boats. It was about preparing them to thrive on the water and fall in love with the sailing lifestyle.
His contributions went far beyond his business. Doug Crane, Sr. was an influential leader in the local marine community, deeply involved in the Jacksonville Marine Association and known for championing boating safety and access throughout the region. In recognition of his service, the Douglas C. Crane Boat Ramp in St. Augustine was named in his honor—a lasting symbol of his legacy.
And of course, he almost always had a sailboat of his own.
Doug laid the keel for what would become St. Augustine’s premier sailing school, charter company, and community. His values of honesty, excellence, and education are still at the heart of everything we do.
“He loved sailing, and he loved the people who loved sailing,” says Doug Jr. “That’s where this all started.”
In 1997, the helm of St. Augustine Sailing passed to James Royse, a man remembered not only for his dedication to the craft of sailing but, more importantly, for his devotion to family, integrity, and legacy. His decision to purchase the company wasn’t just a business move—it was a deeply personal one.
As his widow shared with Rose Ann, James was a man who believed in creating something lasting. His goal in taking ownership of St. Augustine Sailing was to build a legacy with his son, Adam—something they could run together, side by side, as a family. He didn’t just want to grow a business; he wanted to shape a future with his son that they could both be proud of.
“You could feel that everything James did was grounded in love—for his family, for sailing, and for the people who came through these docks,” Rose Ann said. “He saw this as more than work. It was purpose.”
Under James and Adam’s care, St. Augustine Sailing continued to flourish. They expanded charter offerings and worked to keep the school thriving, focusing on creating meaningful, high-quality experiences for every client. Their warm, welcoming approach made the business feel more like a community than a company—a place where clients felt like extended family.
“For my dad, it wasn’t about being flashy,” Adam reflected “It was about doing things the right way, and about enjoying something together—building something meaningful that we could share.”
Though they did not take on the yacht brokerage, the Royse family was instrumental in carrying the business through a period of growth and stability, staying true to the values that Doug Crane had built it upon—honesty, education, and a passion for the water.
James’s legacy lives on in the culture he fostered and the values he upheld. His love for family is woven into the very spirit of St. Augustine Sailing, reminding us all that the most enduring journeys are those shared with the people we love.
“His mark on this business may not have been loud, but it was lasting,” Rose Ann said. “And that’s the kind of legacy that truly matters.”
After years in the corporate world, Alan Bossenger was ready for something different—something more connected to passion, people, and the sea. So in 2003, when the opportunity arose to purchase a respected sailing school in one of the most beautiful coastal cities in America, he took the helm.
“After a corporate career, I wanted to sail more,” Alan shared. “And what better way to do that than to buy a sailing school that already had a great reputation?”
That school was St. Augustine Sailing. And under Alan’s leadership, the business entered a new era of professionalism, structure, and educational excellence.
Fortunately, Alan didn’t have to start from scratch. A seasoned team of captains was already in place, several of whom had been with the company for years. Among them was Chuck Points, who Alan credits as the driving force behind a major leap forward.
“Chuck was instrumental in ensuring that all of our captains were licensed by the U.S. Coast Guard and certified as ASA Instructors,” Alan recalls. “That kind of leadership brought more structure and professionalism—and it elevated the skill of our entire team.”
During his tenure, the sailing school became an affiliate American Sailing certified school, Alan also introduced the SailTime® Northeast Florida program, giving members regular access to beautiful, modern sailboats without the need for ownership—another example of his commitment to making sailing more accessible.
But for Alan, the most rewarding moments weren’t just in the big initiatives. They were in the quiet breakthroughs—those deeply personal moments between instructor and student.
“Some of the most enjoyable times were when a student was struggling to grasp one of the fundamental aspects of sailing. And then—you’d see the lightbulb come on. There was always that moment when it just clicked. That always brought me a lot of joy.”
Alan’s time at St. Augustine Sailing helped lay the foundation for many of the systems and programs still in place today. With a thoughtful approach to leadership and a heart for teaching, he ensured that future generations of sailors—and instructors—would thrive long after his chapter closed.
Long before he was co-owner of St. Augustine Sailing, Chuck Points was one of its most respected captains—a leader known for his deep experience, calm demeanor, and unwavering commitment to doing things right. He didn’t just sail boats—he built sailors.
When Alan Bossenger took ownership in 2003, Chuck was already a cornerstone of the team. Alan credits him with being the driving force behind ensuring every captain at St. Augustine Sailing earned their U.S. Coast Guard Captain’s License and achieved ASA Instructor Certification. Chuck knew that with the right foundation, the company could grow stronger while also lifting the skill level and confidence of every instructor.
“He really set the tone,” Alan said. “Chuck brought structure, consistency, and pride to our training program. That kind of leadership changed everything.”
In 2012, Chuck and Rose Ann were newly married and searching for a new path that would allow them to work together and stay close to the water. Chuck encouraged Rose Ann to tap into her years of sailing experience—having lived aboard a Morgan Out Island Ketch with her children—and start selling boats. The spark caught quickly, and the two built a successful yacht brokerage from the ground up.
Then one day, while discussing putting a boat into the SailTime fleet, Alan simply asked them:
“Why don’t you just buy the business?”
It was a moment that changed everything. In 2018, Chuck and Rose Ann officially took the helm of St. Augustine Sailing. With Chuck’s operational expertise and training background and Rose Ann’s vision and passion for people, the business began a new era of growth, creativity, and community-building.
Chuck remained a hands-on leader, continuing to captain charters, mentor instructors, and manage the growing fleet with precision and care. But more than that, he helped shape a culture that values respect, humility, and learning.
“Chuck’s the kind of leader who never asks someone to do something he wouldn’t do himself,” one team member shared. “He leads by example, and you always feel safe when he’s at the helm.”
Whether he’s running a sunset charter, training a new captain, or fixing something below deck, Chuck’s presence has become synonymous with the quiet strength and high standards that define St. Augustine Sailing.
He doesn’t seek the spotlight—but his influence is everywhere.
St. Augustine Sailing Enterprises, 3076 Harbor Drive,
Camachee Cove Yacht Harbor, St. Augustine, Florida 32084
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Join us for an exciting two-day celebration at St. Augustine Sailing!
May 3 explore our In-Water Boat Show featuring both new and pre-owned vessels, attend free marine workshops like Diesel 101, Medical Preparedness at Sea, Air Conditioning Maintenance, and more.
Enjoy a special Keynote Presentation by Tracy Edwards, renowned sailor and trailblazer.
On May 4th, don’t miss the One-Design Race – sign up to crew or hop aboard the spectator boat and cheer on the action!
Everyone is welcome – come be part of the fun!