While Krieger was a boarding student at a private school called Menlo School in Menlo Park, California, there was study time at night that allowed him to teach himself to play the guitar. He began by first de-tuning a ukulele to the bottom four strings of a guitar and mimicking a record he had. Later, in the mid-1960s, scholar Frank Chin taught Krieger how to play the flamenco guitar. During a Christmas break, Krieger and two classmates took a vacation to Puerto Vallarta where he purchased a peg-tuned Ramírez guitar and took lessons for a few months. He bounced around genres, including flamenco, folk, blues, and jazz and played in a jug band—the Back Bay Chamber Pot Terriers—at Menlo.