It's been a year since Olivia Grayham, a child of the hotel business, struck out on her own as an event planner. It's been a struggle but she's finally poised for a major career boost thanks to her best friend Alexandra, who is taking her wildly popular YouTube lifestyle series onto the high seas for a Caribbean cruise. Tasked with organizing a multifaceted event for the fans onboard and online, Olivia has plotted the journey down to the last detail and planned for every possible contingency, or so she believes. She's no sooner onboard than she faces her first curveball: the ship's longtime cruise director has been reassigned and instead she will be working with his second-in-command, Tony Rieves, who has already begun putting his stamp on the ship's activities. With no option but to adjust to each unexpected development that comes her way, Olivia realizes that there are some things that simply can't be planned or anticipated like falling love.