"[6] As a college-preparatory institution, Isle of Wight Academy has courses emphasizing readying its students for a college education.

Isle of Wight Academy has a number of extracurricular activities for Upper and Lower School students.

IWA offers half-credit courses in fine arts, such as Upper School Band, Chorus, and Audio Visual Technology.

[10] The Upper School participates in the Association of Virginia Academies (AVA) Forensics and Fine Arts competitions, where many students place high in their respective categories.

[14] During his time at IWA in the mid-late 2000's, Daniel Brown was a three-sport athlete (basketball, football, and baseball).