Brian and locals explore what Key West was like in the heart-stopping days of the Cuban Missile Crisis. Then, he heads to New Orleans to relive the swashbuckling story of notorious pirate Jean Lafitte in the early 1800s.

Brian and locals unearth two Kentucky traditions, horse racing and bourbon. They veer off the Bourbon Trail to the birthplace of the American beverage, then gallop back in time to bluegrass horse country for a visit with Secretariat.