St. Augustine Sailing reflects owners’ love of life on the water

Business a major sponsor of Race Week


St. Augustine has a long and distinguished sailing tradition going all the way back to the 16th century. So it’s no surprise that some of today’s most dedicated sailing enthusiasts have decided to drop anchor here.

Among them: Rose Ann and Chuck Points, owners of St. Augustine Sailing and Yacht Sales by Rose Ann – both major sponsors for this year’s St. Augustine Race Week.

At the helm

The couple have been boating and sailing most of their lives.

Rose Ann Points, a native of Oregon, began her boating life cruising the Columbia River and fishing for sturgeon with her family aboard a 27-foot powerboat. In 1996, she moved to Florida and lived aboard a Morgan Out-Island ketch with her three children for 13 years. During that time, she sailed along the East Coast from Maryland to Tortuga, spent nine months traveling throughout the Bahamas and visited several locations in the Caribbean.

Later, while working as a consultant in Orlando, she wanted to vacation aboard a sailboat in the British Virgin Islands and needed to get certification. So, she came to St. Augustine, where she met the man who would become her husband and business partner.

Chuck Points got his start sailing when he was 15. He lived near a yacht club, the members of which were always looking for crews. So, signing on, he began an adventure that would chart his course through life.

He served with the U.S. Marine Corps in Vietnam, after which he returned to the sailing life. He sailed in Asia and Europe and a variety of environments from Lake Superior to the South China Sea.

He came to St. Augustine in 2004 to rent a boat and, when it was discovered that he had a captain’s license, he was offered a job. And that’s where he was when the future Rose Ann Points walked through the door.

The couple married in 2012 and, in 2017, they purchased St. Augustine Sailing from the previous owners. Their passion for sailing, boats and the water made the business a natural fit for them.

On the water

Under the Points’ ownership, the business has thrived.

St. Augustine Sailing Enterprises has been described as a luxury adventure experience that accommodates different budgets. The secret of its success may lie in the variety of its offerings.

Its private, captained charters sail from Camachee Cove Yacht Harbor. These are a popular choice for family outings and special occasions and are completely customizable. They can be booked for durations between two hours and overnight.

Specialty charters often include catering. There’s a brunch sail, an afternoon reception-style sail, sunset sails and full-dinner sails with a private chef on board.

Themed sailings add some drama to the experience. The Tuxedo Tuesday Cruise features an Agent 007 James Bond impersonator who shakes and stirs drinks. The Thirsty Thursday Sail Away includes a selection of wine and cheese. Once-a-month Sip & Sail Saturdays incorporate tastings of five seasonal wines with discussion by a knowledgeable sommelier.

There are also a number of land and sea packages.

Coming up are two months of special events: one for the ladies in May and the other for guys – though women are welcome, too – in June.

The first pairs brunch and mimosas with a sail aboard a yacht. The second allows customers to chart a course with the captain, sail it and then sit down with the captain afterward to enjoy a beer and get some professional feedback.

Beyond the cruises, St. Augustine Sailing offers sailing lessons and membership in SailTime, a worldwide sailing club that allows members to rent a watercraft anywhere there is a franchise.

Rose Ann Points said what she likes best about her business is helping people to fulfill a dream they’ve had for a long time.

“I love getting to know (the customers),” she said. “For me, it’s all about the experiences. It’s about the adventure. So, getting to know them, finding out what it is that they want and then helping them find a path to fulfill that dream and make it a reality for them.”

For Chuck Points, it’s all about getting out on the water.

“You’re out sailing quite a bit,” he said. “It’s quite enjoyable, and the people are great.”

The fleet of 10 yachts is always kept fresh; none of the boats is older than three years.

Aside from the excursions and other services offered by St. Augustine Sailing, Yacht Sales by Rose Ann handles the sales of these watercraft.

Race Week

The fifth annual St. Augustine Race Week, hosted by the St. Augustine Yacht Club, was held Friday, April 16, through Sunday, April 25. The eight-day celebration included parties, food, music and, of course, sailboat racing.

The event raises funding for the John Daniel Meehan Youth Sailing Scholarship Program, which sends kids ages eight to 18 to summer sailing camps.

The week kicked off with the two-day Youth Sailing Regatta, in which junior sailors up to age 18 raced in Matanzas Bay between the Castillo de San Marcos and the Bridge of Lions. The race was sponsored by Yacht Sales by Rose Ann.

Winners were:

First Place: Thomas Schuerger, Cheyenne Dooley

Second Place: Grace Jones, Jack Allen

Third Place: David Vinogradov, Justin Trebon

The two-day Inshore Racing Series was held April 20 and 21. These races were held on the Tolomato River north of the Francis & Mary Usina Bridge near Vilano Beach.

Winners were:

First Place: Tim Tucker (Fireball)

Second Place: Paul Hellings (Girl Dog)

Third Place: Brett Staples (Easy Button)

The “big boats” took to the Atlantic on April 22-24 for the Offshore Racing Series. There were four classes. Performance Spinnaker Class and Performance Non-spinnaker Class were sponsored by Pusser’s Rum. Cruiser Spinnaker Class and Cruiser Non-spinnaker Class were sponsored by Meehan’s Irish Pub.

Winners were:

Cruiser Non-Spinnaker

First Place: Brianne Petit-Muller (Veria)

Second Place: David Hightower (Stray Dog)

Third Place: David Locy (Sage)

Cruiser Spinnaker

First Place: Norman Church (Obsession)

Second Place: Carl Kennon (Flamingo 2)

Third Place: Eddie Evans (Naut-on-Call)

Performance Non-Spinnaker

First Place: Mark Dixon (Pura Vida)

Second Place: Robert Newsome (Snowgoose)

Third Place: Henry Korous (Morgana)

Performance Spinnaker

First Place: Tim Tucker (Rockstar)

Second Place: Bradley Stowers (Hillbilly)

Third Place: Bubba Futch (Cheetah)

For further information about St. Augustine Sailing and Yacht Sales by Rose Ann, go to

For information about Race Week, go to