Andrew has inherited a great deal of money from his father, but it came with some unusual stipulations. The first of these is to organize a private cruise for fifty people, all over the age of fifty. While it's a challenge for Andrew—a thrifty homebody bordering on curmudgeonly—it's nothing new for his wife, Abigail—a bossy extrovert who loves to plan a party. Andrew and Abigail choose to invite family and friends to join them as they cruise the Channel Islands off the California Coast. The cruise is full of vibrant people, including Hank, Abigail's sweet, hard-of-hearing father; three spunky women in their 90s who like to hula; and Cousin Olivia, who just may have it in for Abigail. The group comes face-to-face with the different stages of aging as they enjoy and survive adventures and misadventures on the islands while experiencing the vacation of a lifetime.