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Jennifer and Meg Swift are two sisters who are very close despite living far apart. Jennifer is in Salt Lake City, running a successful restaurant she started with her late husband and raising her teenaged son Simon, Meg stayed in their hometown of Hazelwood, helping their parents run the local bakery.

Meet the Libner brothers: Marvin, the oldest, is a sergeant in the U.S. Air Force. Buddy, the middle child, is a timid dreamer. Bobby, the youngest, is a handsome rebel in reform school. As kids, they fought a lot and as adults, they barely speak. In the summer of 1963, their tough and eccentric father, Fred, gives them a task: to bring a 1954 Cadillac, bought for their mother, Betty, from Detroit to Miami. As the trip goes on, the three brothers fight and begin to reconnect with each other, while trying to keep the Caddy in mint condition.