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.