Organized and structured event planner Olivia gets a game-changing opportunity to organize logistics for a major event: an Internet lifestyle series set on a luxury Caribbean cruise ship, hosted by her best friend, cooking and wellness star, Alexandra. Olivia meets her match in the charming Tony, who is on a trial run as Cruise Director and puts his personal stamp on the cruise experience, but they must work together to make the cruise go off without a hitch, for the sake of their careers and friendships, as Olivia realizes that some things can't be anticipated or scheduled - like falling in love.