On Thursday, May 26, 2005, Holloway and 124 fellow graduates of Mountain Brook High School, located in a wealthy suburb of Birmingham, Alabama, arrived in Aruba for a five-day, unofficial graduation trip. The graduates were accompanied by seven chaperones. According to teacher and chaperone Bob Plummer, the chaperones met with the students each day to ensure nothing was wrong. However, Jodi Bearman—the chaperone who organized the trip—has stated, "the chaperones were not supposed to keep up with their every move".