Rose Ann Points had never so much as stepped a Sperry onto a sailboat when she and her then husband made the bold decision in 1996 to uproot their comfortable family life in Oregon and travel the Caribbean aboard their own vessel. But as wild as the idea may seem, Points needed little convincing when her husband spontaneously suggested the adventure: She had grown up in a small town in Oregon with a dream to see the world, and aspired to a career as a flight attendant.
So she agreed (despite a ferocious propensity for seasickness) and before she knew it, she and her children—daughter Toste and sons Derk and Lance, then just twelve, ten, and nine, respectively—were packing the single two-by-two box they were each allocated for their belongings. She still treasures the memory of “watching each of them go through their possessions and debate what to put in the box,” Points recalls. Toste chose some of her porcelain dolls, while Lance packed his collection of rocks and one pair of underwear (a move she had to help him amend).
The family then drove to Florida and boarded their newly purchased forty-one-foot Morgan Out Island ketch (a double-masted sailboat) named Tranquility and moved aboard for what would become thirteen years. Those first few weeks, though, brought trial and tribulation, as each person worked to find their sea legs and hone their sailing skills, down to learning how to tie proper sailors’ knots. “We knew nothing about sailing,” Points says. “We had not taken any classes or studied any books. It was true on-the-job training.”
The family’s strength as sailors would be tested within only months, when they docked at Allen Cay in the Northern Exuma Islands as a hurricane approached. They anchored the boat in what they believed to be a protected place, but as the swirling winds shifted, it became a literal all-hands-on-deck moment—each child took on the rather grownup tasks of steering the boat and raising the anchor while Points and her husband, in a dinghy, unmoored the boat so they could safely move out of harm’s way.
As the years progressed, Points came to appreciate most the ability to teach her children to appreciate different cultures and different ways of life. The family would stop at smaller, less populated islands where the few people who did reside there would greet them. Days were spent learning the local customs, cooking indigenous foods, and exploring the land. In between, Points boatschooled the kids; this was before widespread use of computers, so she relied on the natural surroundings to teach them subjects including biology, math, and geography, with the onboard atlas serving as the primary schoolbook. For a brief stint following a hurricane, they lived with a family in George Town on Great Exuma to help with recovery efforts while the kids attended a local school.
Plenty of funny stories emerged from life on the water, too, like the time Lance needed to make his way back to the boat after exploring an island, but didn’t want to walk the long way along the shore. Instead, he found an old wooden drawer in some debris and, using a stick of wood as an oar, made his way back across the water. Or the day Toste surprised the family with a homemade carrot cake, using only the ingredients she had on board—which did not include carrots, but satisfied everyone’s sweet tooth just the same.
Stopping on islands gave the family an opportunity to stock up on provisions like sugar and flour, but while at sea, they relied on what they could catch for food. “My kids ate things they would never eat today,” Points says. “We would walk the rocks and pop off cockles and boil them. We would eat anything we found.” To this day, her children rarely eat lobster after so many years of living on it as a staple. One of her fondest memories took place on Grand Bahama, when Points learned how to make crab mac and cheese from one of the local women, who fed watermelon to her caged land crabs to make the meat sweeter.
As Points’s daughter approached high school age, the family made the decision to drop anchor in the Florida Keys so the kids could attend school and get a more traditional education. Every holiday and school break, though, they were back out exploring the sea.
Years later, when the kids had gone off on their own, Points decided to hone her sailing skills even further by taking lessons at St. Augustine Sailing, in St. Augustine, Florida. Within a year, she became a partner in the business with her new husband, Chuck Points. Today, her three children are active in the company, too, and are still avid sailors who are now raising their own children on the water.
Looking back, Points credits this decade-plus of experience with giving her tenacity and grit, along with an immense self-confidence that would go on to help her achieve her business goals. To empower other women in the same way, she created Women on the Water, an organization designed to enhance the lives of women by teaching them to sail with confidence—including how to perform maintenance, to navigate, and to race—ideally giving them skills they can use to overcome adversities and boost their mental health. After all, “My life has been filled with adventure and experiences,” she says, “but it’s the people we encountered along the way who have really made it fulfilling.”