SailTime Northeast Florida proudly celebrates its 20th anniversary, marking two decades of inspiring confidence, connection, and community on the water. Founded in 2003, the base has become a cornerstone of St. Augustine’s maritime culture—helping sailors of all experience levels embrace the sailing lifestyle through education, shared ownership, and expert guidance.
Under the ownership of Rose Ann and Chuck Points, SailTime Northeast Florida has grown into a dynamic, full-service hub for boating education and access. The base operates in partnership with St. Augustine Sailing, an American Sailing certified sailing school, and All Points Yacht Sales, the regional Jeanneau dealer and brokerage. Together, these three organizations form a seamless ecosystem supporting sailors from their first lesson to yacht ownership and beyond.
A Legacy Built on Strong Foundations
Originally launched by Alan and Becky Bossenger in 2003, SailTime Northeast Florida was created as an extension of their already successful business, St. Augustine Sailing, which has served the sailing community since 1985. When the Points purchased the SailTime base in 2018, they inherited not only a strong foundation of professionalism and community but also an opportunity to evolve the model into something even more integrated and client-focused.
“As avid sailors, we were drawn to SailTime because it perfectly aligned with our personal passion and professional vision,” said Rose Ann Points, Managing Member of SailTime Northeast Florida. “Many of our yacht brokerage clients dreamed of owning a boat but weren’t quite ready. SailTime allowed them to enjoy the lifestyle immediately while gaining experience, confidence, and community along the way.”
A Seamless Journey from Learning to Ownership
What began as a challenge—integrating multiple business lines into one cohesive client experience—has become SailTime Northeast Florida’s signature strength. Members can learn to sail, gain real-world experience through SailTime memberships, and eventually transition into yacht ownership, often within the same trusted network.
“The synergy between St. Augustine Sailing, SailTime, and All Points Yacht Sales creates a natural pathway for people to live their dreams,” said Points. “We’ve watched countless sailors start from scratch, become confident captains, and ultimately purchase their own yachts. It’s deeply fulfilling to see that transformation.”
This integrated approach has also encouraged members to contribute back to the program. Several have placed their new boats into the SailTime fleet in St. Augustine, allowing them to enjoy ownership while helping others discover sailing for the first time.
A Location Like No Other
Operating from Camachee Cove Yacht Harbor, SailTime Northeast Florida enjoys one of the most versatile sailing environments in the region. St. Augustine’s Intracoastal Waterway and nearby inlet provide protected conditions for beginners and direct access to offshore adventure for seasoned sailors. The area’s mild climate ensures year-round sailing, and its historic waterfront offers a scenic backdrop rich with maritime heritage.
From day sails and river cruising to weekend voyages to Cumberland Island or Amelia Island, members experience the flexibility to grow at their own pace while surrounded by dolphins, manatees, and the charm of America’s oldest city.
Fleet and Future
As the Jeanneau dealer for Northeast Florida, All Points Yacht Sales and SailTime Northeast Florida maintain a modern fleet of performance-oriented sailboats, currently featuring two Jeanneau 349s with expansion plans including the Jeanneau 350, 380, and 415. This ensures members and students always have access to contemporary vessels that reflect the latest advancements in design, safety, and comfort.
“Our members gain hands-on experience with the boats they may one day own,” said Points. “It’s an exciting and confidence-building part of what makes SailTime unique.”
A Culture of Community
Beyond sailing and education, the base is known for fostering camaraderie through events like the annual Ladybug Event, a three-day celebration of sailing, seminars, and community. The annual Ladybug Event coincides with the Seven Seas Cruising Association’s Spring GAM, further expanding opportunities for education and fellowship.
Stories of Transformation
Every SailTime Northeast Florida member has a story, and many share a common thread—discovering confidence, joy, and a renewed sense of purpose on the water.
- James joined to gain the experience and education needed to sail anywhere. His journey led him from beginner to confident cruiser. Watch his story
- Florentino sought not only to learn to sail but to master vessel maintenance in preparation for his retirement afloat. Watch his story
- Ray and Lorraine wanted to spend more time together entertaining friends and enjoying the St. Augustine waterways. Watch their story
“Watching members progress from dreaming about sailing to confidently skippering their own boats is what keeps us inspired,” said Points. “SailTime gives them access, structure, and a community that truly supports their goals.”
The People Behind the Helm
The People Behind the HelmChuck Points’ lifelong connection to sailing began at age twelve, cleaning boats at a yacht club—a start that led to a lifetime at sea, spanning the North Atlantic, Caribbean, Mediterranean, and Pacific Oceans. A Vietnam veteran, Chuck later became an American Sailing Instructor of the Year, known for his calm presence and guiding philosophy: sail to the comfort level of the least experienced person aboard.
Rose Ann’s journey took a different course. She didn’t grow up around boats but spent thirteen years living aboard a Morgan Out-Island Ketch, an experience that shaped her resilience and perspective. After years of global travel in emergency management, she rediscovered sailing as a student at St. Augustine Sailing—where Chuck was her instructor. The two later formed both a personal and professional partnership, combining their expertise to expand sailing access in Northeast Florida.
“Sailing gave me more than skills—it gave me confidence, community, and purpose,” said Rose Ann. “Those lessons are the heart of how we lead today.”
The couple now owns a Jeanneau 410 and continues to mentor sailors at every level, helping them progress from ASA courses to cruising the world.
Looking Ahead
As SailTime Northeast Florida enters its third decade, Rose Ann and Chuck remain focused on thoughtful, sustainable growth—expanding opportunities for education, mentorship, and community engagement while preserving the personal, high-quality experience their members have come to love.
“We’re not just teaching people to sail,” said Rose Ann. “We’re helping them build the skills, confidence, and mindset to live their dreams—on their own terms.”
About SailTime Northeast Florida
SailTime Northeast Florida operates from Camachee Cove Yacht Harbor in St. Augustine, Florida, offering fractional sailing memberships, ASA-certified instruction, private charters, and yacht brokerage through All Points Yacht Sales. As part of the global SailTime network, the base provides innovative, cost-effective access to modern sailboats while fostering education, confidence, and community on the water.
For more information, visit SailTime Northeast Florida or info@staugustinesailing.com.