Host Faruq Tauheed takes brother and sister Ashley and Elliott back to their grandparents' hometown of Martha's Vineyard, Massachusetts. During their trip, they get a sailing lesson and learn that their fifth great-grandfather Henry Osborn was taken prisoner on a boat in the Revolutionary War. While feasting on lobster, they discover that their third great-grandfather Samuel Osborn went from debtor's prison to owning a fleet of whaling ships. A surprise visit from their parents allows them to share their found history.