Uncle and nephew Al and JR revisit their journey to Havana, Cuba, where they explored the 32 blocks of downtown that their ancestor helped develop and share how the journey allowed them to reconnect in ways they couldn't have imagined.

Siblings Ashley and Elliott reminisce about their trip to Martha's Vineyard, Mass., where they sailed on a boat much like the one their ancestor was taken prisoner on during the Revolutionary War and visited an inn with special family ties.