When a young shipwrecked immigrant named Viola takes a chance on the "wet foot, dry foot" policy of the mid-nineties and washes up amidst the shore of glitzy Illyria, Florida, she finds herself a stranger in a fabulously strange new land. Thinking her twin brother has drowned, Viola throws herself more...
into a new gig as assistant to Orsino, a wealthy Floridian with a serious case of love sickness for a wealthy lady, Olivia. Having disguised herself as a boy to become Orsino's right hand man, Viola (now Cesario) is tasked with delivering his adoring valentines. But as Viola woos in her boss's name, she falls head over spiky heels for the man himself, while Olivia turns her affections to the intriguing young messenger boy, Cesario (also Viola).