Upper School students are enriched and challenged by a diverse curriculum that offers regular, honors, and Advanced Placement (AP) courses, often with opportunities to receive college undergraduate credits for these college-level courses. In addition to the more traditional academic offerings, many students are involved daily in courses dedicated to the visual and performing arts. The Upper School puts on major theatrical productions, musicals, ballets, short plays, and concerts. Sixty-three faculty members, most of whom hold advanced degrees in their subject areas, teach the curriculum.

The academic day at Pine Crest usually consists of six courses or their equivalent during a nine period academic day.

A typical freshman schedule consists of: English I, World Civilization II, a modern language, science, mathematics, the Enrichment Sequence, and Physical Fitness/Health classes, for a total of seven hours. A lunch period and one study hall occupy the remaining two periods of the day. The Enrichment Sequence, which consists of trimester offerings of Ethics, Basic Communication, and either Fundamentals of Art or Principles of Drama may be satisfied in different ways. Students interested in Forensics may take that course in lieu of Basic Communications. Students interested in fine arts may take Band, Chorus, Drawing and Painting, or Sculpture and Ceramics to satisfy the arts component, or they may delay the Enrichment Sequence or portions of it until the sophomore year. All freshmen take Physical Fitness/Health, but they may take Ballet/Health in its place. Freshmen who elect to take ballet may not use the credit to satisfy a segment of the Enrichment Sequence.

The academic load for sophomores, juniors, and seniors, who have satisfied the Enrichment Sequence and Physical Fitness/Health requirements for graduation, is six courses, or their equivalent in hours. Students who take advanced placement courses that meet more than five periods per week must compute the daily load. A course that meets a double period every day counts as two hours. A course that meets a double period every other day counts as one and a half hours. For example, a student who takes AP Biology (two hours), Calculus AB (one and a half hours), and AP Psychology (one and a half hours) has already accounted for five of the required six hours, even though they have taken only three courses.