A Chicagoan inherits an old yacht. He, his wife, daughter and son fly to a Caribbean island and hire a dubious Captain Ron to sail them on an adventure to Miami.
The arrival of wealthy bachelors in town causes an uproar when families with single daughters aggressively seek engagements, including the Bennet family, with five eligible daughters.
A man who seemingly has it all together, being smart, talented, funny, and popular, is secretly overwhelmed by expectations of himself and those of his parents, and suffers what is assumed to be a horrible accident.