Phillip Winters is a computer guy with a dream to set sail. His lawyer wife Lucy only half shares his vision but begrudgingly follows Phillip to their first sailing class in the sailing capital of America, Annapolis, MD. She excels, while he falls behind. Setting out to find the perfect boat, whether his wife approves or not, Phillip finds a storm-ravaged boat and gets in over his head, much to his wife's disapproval. They move to Beaufort, NC, and fix up the derelict vessel without having the first clue of how to fix a boat or even how to sail for that matter. They quickly realize that it is a task they are ill-equipped to handle, and one which they lack the experience or know-how to tackle. Thankfully, like so many who have gone before them, they have the financial means to push forward, even if they should run away. A brief stay in a town that resembles a third-world banana republic and a run-in with what all Southerners affectionately call "water bugs", they manage to launch their dream boat and set sail after a rum-soaked christening in Oriental, the sailing capital of North Carolina. Bumping down the coast to Florida, hopping from port to port, the couple experiences the highs and lows of the live-aboard lifestyle, including surprise expenses, sweaty nights on the high seas, and morally questionable port adventures with fellow boat owners. The Sailboat is a cautionary tale about boat ownership and relationships and demonstrates to those who are dreaming of ditching their COVID cocoon by heading out on the high seas that the live-aboard life is rarely smooth sailing.