Two rivals. One competition. Winner takes all. Olive spends her days taking awkward family photos. Her dreams of being a travel photographer are thwarted by a debilitating phobia. Ready to face her fears, Olive enters the Catalina Isle of Love contest where the winner will tour the world as staff photographer for a popular travel magazine. Olive’s biggest opponent is Gabby, who wins the competition every year and has a reputation for doing anything to succeed. Gabby manages her Italian family’s chain of pizza restaurants. She’s ready to break free from her large, overbearing family and live her secret dream of being a photographer. For Gabby and Olive, nothing will stand in their way of winning…except maybe love.