Rose Ann Points, Owner of St. Augustine Sailing, and 40 Years of Sailing in St. Augustine

ST. AUGUSTINE, Fla. - Rose Ann Points could not swim and had never sailed when her then-husband came home one day and said he wanted to sell the house and buy a sailboat. She was not yet 30 and had three small children. Three decades later she owns St. Augustine Sailing, the 40-year-old charter company and sailing school at Camachee Cove Yacht Harbor, holds a 50-ton master captain's license and is about to run her ninth Nights of Lights season on the water.

The company's website lists four Nights of Lights packages for 2026-27, from a 75-minute dessert sail at $99 a person to a three-hour chef's dinner at $425 a person. The city's holiday light display switches on Saturday, Nov. 21, and runs through Jan. 18, 2027, according to the St. Augustine tourism bureau. The company says its boats sail every night of the festival, weather permitting, and usually sell out.

One box each

Points grew up in a small town in Oregon, where her family fished for sturgeon on the Columbia River from a 27-foot powerboat, she said in an interview published by the American Sailing Association. When her husband proposed moving the family aboard a sailboat in Florida, the house in Washington state sold in seven days. He then handed out four moving boxes, each about 2 feet square, one for her and one for each child, and told them that whatever they wanted to keep had to fit inside.

Her youngest son packed a Tonka truck, his rock collection and a single pair of underwear, she told the ASA. The family bought Tranquility, a 1977 Morgan 41 Out Island ketch, through a Fort Lauderdale broker and learned to handle it in Marathon in the Florida Keys. They went on to the Keys, the Dry Tortugas and then across the Gulf Stream to the Bahamas.

Points moved to Florida in 1996 and lived aboard the ketch with her children for 13 years, according to a 2021 profile by writer Shaun Ryan that the company republished on its site. In that time she sailed the East Coast from Maryland to the Tortugas and spent nine months in the Bahamas. "My kids grew up and decided to go to college and became landlubbers," she said in a 2025 interview with Flagler Broadcasting, so she came back ashore and eventually settled in St. Augustine.

Meeting Chuck

She was working as a consultant in Orlando and wanted to charter a boat in the British Virgin Islands, which meant she needed a sailing certification. She came to St. Augustine Sailing for the class, the 2021 profile says, and met Chuck Points, a captain who had come to the school in 2004 to rent a boat and been offered a job on the spot. Chuck Points started sailing at 15 and served in the Marine Corps in Vietnam.

The two married in 2012 and, according to the company's 40th anniversary history, started a yacht brokerage together at Chuck Points' urging. The school's owner at the time, Alan Bossenger, eventually asked them, "Why don't you just buy the business?" They did. The company's own pages give the year as 2017 in one place and 2018 in another, and the Points are the fourth owners since Doug Crane Sr. founded the school and sailboat dealership in 1985.

What she runs now

As owner, Points manages the company's member clubs, its SailTime Northeast Florida franchise, its American Sailing Association school and the brokerage, now called All Points Yacht Sales, according to the ASA, which named her a featured instructor. She founded Women on the Water, known as WOW, with a mission "to enhance the lives of women through education, practical application, and access to sailing vessels." She told the ASA her most memorable class was her first ASA 105 coastal navigation course with four experienced students, and that the school's team has certified more than 1,000 sailors.

Her youngest son, Lance Burkin, now maintains the fleet, she said in the Flagler interview, and the company's fleet page credits him with keeping the boats ready. That fleet runs from 21 to 45 feet and includes six charter yachts and three small boats used for lessons. The 2021 profile also quoted Points on what she likes most about the business: "For me, it's all about the experiences. It's about the adventure."

Nights of Lights by the numbers

The company's Nights of Lights page says its boats leave from the Camachee Cove marina at the St. Augustine end of the Vilano Bridge, which keeps guests out of the downtown parking crunch, and that parking at the marina is free. Every price carries a "++" mark, the charter-industry shorthand for tax and gratuity added on top. The starting prices below are based on a party of six.

• Glitter: three hours, a four-course dinner cooked on board by a private chef and paired with wines, with 4 p.m. and 7:15 p.m. departures, from $425 a person.
• Sparkle: two hours on the Matanzas River with a box of sweet and savory bites and a glass of sparkling wine, departures from 4:45 p.m., up to 10 passengers, from $129 a person.
• Twinkle: 75 minutes under the Vilano Bridge with a dessert and a festive drink, departures from 6 p.m., up to 10 passengers, from $99 a person.
• Shared tour: a seat on an open charter with other guests, a minimum of two and a maximum of six passengers, from $129 a person.

Points also runs an annual Ladybug Event, a spring weekend with an in-water boat show, workshops and a regatta. The third one, held March 6-8, 2026, with the Seven Seas Cruising Association, brought in Volvo Ocean Race skipper Lisa McDonald as keynote speaker. Admission was $100 a person for the workshops and seminars, according to the event page.

Learning the way she did

St. Augustine Sailing is a certified ASA training facility, and the entry-level ASA 101 Basic Keelboat class runs two days at the marina with two to four students on a Hunter 216, a Hunter 22 or a Pearson Ensign. The course covers terminology, points of sail, tacking, jibing, crew-overboard recovery and docking. The site does not list a price, and classes continue through ASA 106.

Points told Flagler Broadcasting the school takes people "from zero to hero," from first-timers to sailors learning celestial navigation and passage making. Reservations for Nights of Lights sails and classes can be made at sta-sail.com or by calling 904-829-0648. The office is at 3076 Harbor Drive at Camachee Cove Yacht Harbor.

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