A FAMILY AFFAIR
For Rose Ann Points, sailing isn’t just a family activity – it’s a family business. That’s because when you book a luxury sailing experience with St. Augustine Sailing, you’re in the capable hands of a family that has lived and breathed the salt air for most of their lives. After years of making her family at home living on boats, Rose Ann has built that strong family bond into her business.
“It wasn’t until my mid-twenties that I started spending time on boats,” says Rose Ann, co-owner, Captain, and broker at St. Augustine Sailing. “At first, it was a 27-foot Bayliner Cabin Cruiser that my kids and I would take out on the weekends when we lived in Vancouver, Washington.” Then, when Rose Ann was 30, the family decided to sell everything they owned and buy a sailboat to live the life of adventure. They purchased a 41 Morgan Out-Island ketch (a double-masted sailboat) named Tranquility and moved aboard for 13 years. She says, “They loved it. It was just the most wonderful time, giving my kids that connection to the sea. And we’ve never looked back!”
Rose Ann’s children are all actively involved in the business. Her daughter Toste serves as the main point of contact for passengers looking to book an excursion. Her two sons also help man the helm, so to speak. Derk is a photographer and videographer who documents the myriad momentous occasions on board. Lance manages St. Augustine Sailing’s extensive fleet of sailing yachts, keeping them afloat and in tip-top shape. Lance’s wife, Amberle, creates the delectable bites on-board, curating an extensive menu of options including lush charcuterie boards and perfectly-paired beverages. And speaking of spouses, Rose Ann’s husband, Chuck Points, is not only the co-owner of St. Augustine Sailing. He’s a steady, solid presence, overseeing all sailing operations and serving as the business’s main delivery Captain. Chuck is also an award-winning ASA instructor who has guided numerous individuals on their path to becoming sailing instructors.
“Chuck actually came in to rent a boat, before I was involved with the business,” chuckles Rose Ann. “He got to talking to the previous owners and it turned out he had a Captain’s license and a whole lot of experience on the water. He’s sailed all over the world – the breadth of his knowledge is so impressive! So they hired him. And that’s how we met – I walked through the door and there he was. It makes this business even more meaningful for us because it’s part of our love story.”