Josh tells himself he’s the luckiest guy in the world. Living on his sailboat and taking tourists on occasional chartered trips, he’s not tied down to routines and responsibilities. He even named his sailboat Solitude, because that’s what he enjoys much of the time. Danae works at a boat company, and she just got promoted—sort of. To keep her dream job, she must get her opinionated coworkers to all agree on a marketing plan. Her boss directs her to set up a week-long sailing tour with them as a work trip and a bonding experience. At first, Danae isn’t completely on board with Josh’s laid-back approach to the excursion. But during visits to quaint New England towns and seafaring adventures, she and Josh start to see one another’s true colors...and Josh begins to question his solitary life.