This study explores an innovative Civil Rights program, one that brings together students from two Midwestern high schools, a majority Black public charter school and a majority white Jewish private suburban school. Students participating in this program culminate their study of the Civil Rights Movement by boarding a chartered bus and traveling together for eight days through the Deep South. During the eight-day journey, students visit seminal Civil Rights locations and learn about the Civil Rights Movement first-hand. This unique experiential learning opportunity resulted in students gaining valuable knowledge about the Civil Rights Movement, but it also challenged students in ways that they did not anticipate as tensions emerged regarding differences in cultural backgrounds and experiences. Ultimately, these rather unexpected challenges resulted in students learning about themselves and each other.