In 2011, Linda Jackson and her husband walked away from their Northern California routine and committed to living full time on the water. It was not a short escape or a retirement fantasy put off for later. For them, the ocean became home, and the boat became the place where everyday life happened. Jackson says the idea was years in the making, shaped by a moment when she knew she needed a different path.
That turning point came back in 2001, when the dot-com bubble burst and the aftermath of 9/11 left her craving a reset. She had loved boating since college, and she and her husband decided to take a year-long sailing break. On a 34-foot performance cruiser, they traveled from Northern California to Zihuatanejo, Mexico, and back again. Somewhere between the long passages and the new coastline, they realized this was more than a one-time adventure, it was the life they wanted to build.
Making it permanent took a decade of deliberate choices. Jackson left her sales and marketing executive role and started her own consulting firm, creating a way to work with more flexibility. The couple bought a 50-foot live-aboard vessel, then spent about a year fixing it up before it even touched the water. They also began stripping down everything they owned, digitizing documents and photos and refusing to keep a storage unit as a backup plan.
When they finally set sail in 2011, they had to learn how to live independently at sea. Over time, Jackson and her husband, whom she affectionately calls the Captain, developed the skills needed for an autonomous life on the water. They sometimes sailed with a small crew of one to four people in addition to themselves, pulling from friends, family, and people they met through online crew sites. The practical realities were constant, but so was the thrill of living in motion.
In 2019, they upgraded again, buying an 80-foot yacht in Florida called SV Duende. They took her through the Panama Canal and up the west coast of Mexico, then spent years improving the boat for major ocean voyaging. Their most recent journey began in April 2025, crossing from Mexico toward Tahiti, then spending around 90 days exploring islands in French Polynesia. After that came a milestone, a long voyage across the South Pacific to Fiji with only the two of them handling the boat.
Jackson admits the lifestyle is not for everyone, but she loves the unexpected perks, like anchoring near Bora Bora’s famous overwater bungalows that can cost around $5,000 a night. For years, she kept her experiences private in a diary she calls the Shellphone Chronicles, using it as a creative outlet while at sea. After a client mentioned Substack and a friend encouraged her to go public, she began sharing the journal with readers, and she says the response has been surprising. More than anything, she credits the years afloat with turning her into someone braver than she ever expected to be.
Would you trade a traditional home for a life at sea, or do you prefer your adventures to stay on shore? Share your thoughts in the comments.
