Host Faruq Tauheed looks back at memorable moments, including a relative who gave John F. Kennedy the keys to Mexico City, a connection to downtown Havana, Cuba, and an African American ancestor who owned land in Tennessee before the Civil War.

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.

Host Faruq Tauheed takes father and daughter Paul and Kalina to the Civil War battleground in Port Republic, Virginia, where they discover that Paul's great-grandfather Austin D. Springer was a drummer boy for the Union Army. At the battlefield, Paul and Kalina learn that Austin was taken prisoner by the Confederate Army but escaped and hid in slave huts until he made his way back to the Union Army. Paul, a Vietnam veteran, connects his own experience and believes that being a combat vet is in his genes.

Host Faruq Tauheed takes uncle and nephew Al and Jr. on an ancestral trip to Havana, Cuba, where Al learns that his grandfather Joseph Barlow owned and developed 34 blocks of downtown Havana, including the now-famous suburban neighborhood Buena Vista. But due to an unfortunate turn of fate, Joseph Barlow lost his riches in a political coup. As the two men connect over their own entrepreneurship, they learn where their family's resilience came from.

Aunt and nephew Tammy and Julian go on an adventure in Brooklyn to learn their relation to undertaker John Baisley, who helped bury the city's dead in the 1856 epidemic, and to James Howell, who was an integral part in building the Brooklyn Bridge.

Mom and son duo Sharee and Davone travel to Nashville, Tennessee, where they learn that their fourth great-grandfather Larkin Ford was a part of an 1840s landmark Tennessee case in which he was awarded the farm that he worked on as a slave.

Grandpa and grandson Evan and Scott travel to Montana to learn that Evan's great-grandfather was an integral part of the 1862 U.S. western states expansion and that two of his uncles were prisoners of war in WWII, both receiving Purple Hearts.

Host Faruq Tauheed takes half-siblings Michelle and Rob to Mexico City, where they discover their relation to a famous Mexican political family and learn that their second cousin Ernesto gave the keys to Mexico City to President John F. Kennedy.