The Bolles School is an American private college preparatory day and boarding school in Jacksonville, Florida. It has a lower school (including pre-kindergarten), a middle school, and a high school, spread across four campuses around the Jacksonville area, and enrolls about 1,800 students a year. The school was founded in 1933 as an all-boys military academy. It dropped its military focus in 1962 and became coeducational in 1971. Itsathletics program has been noted by Sports Illustrated magazine and the Florida High School Athletic Association.
 
The school was founded as an all-boys' military academy in 1933 by Agnes Cain Painter, a friend of philanthropist Richard J. Bolles. The original campus, now known as the San Jose Campus, was founded in a former hotel on San Jose Boulevard near the east bank of the St. Johns River. Bolles announced that it would drop its military status in 1961 and the graduating class of 1962 ended the military era. It began admitting girls in 1971. Today, the ratio of males to females is close to 1:1.
International students have enrolled at Bolles since the late 1930s, and the school maintains separate boys and girls boarding facilities for 90 students from other states and 22 foreign counties.The school also has an active Student exchange program with other schools in Japan, France and Spain. Participants live with the host family while attending school.
Upper School (grades 9-12) - San Jose Campus (Jacksonville)
Middle School (6-8) - Bartram Campus (Jacksonville)
Lower School (pre-kindergarten-5) - Ponte Vedra (Ponte Vedra Beach) & Whitehurst (Jacksonville) Campuses
 
In 2005, Sports Illustrated named Bolles's athletic program the ninth best in the country, and second best in Florida. Of the top twenty-five schools, Bolles was the only one with an Upper School enrollment of under 1,000 students. Bolles has received the Florida High School Athletic Association's Dodge Sunshine Cup/Floyd E. Lay All-Sports Award (given to the best overall athletic program in each school type/size classification in Florida) for eleven consecutive years. The school has recently won state championships in baseball, cross country, football, soccer, swimming, tennis, track and field, crew, volleyballand wrestling.
During football season, this billboard in front of the school is used to display the team's next opponent

The swim team, which established prominence under Coach Gregg Troy, who now coaches at the University of Florida, is highly successful. Bolles' boys and girls swim teams have been state champions every year since 1984, usually sweeping most events at state meets. The girls team has won the National Championship nine (9) times, while the boys team has won or been runners-up for the National Championship eleven (11) times. The school's swimming facility has its own offices, weightroom (not separate from the weightroom that the rest of the school uses), and two swimming pools (one Olympic-sized). Bolles has had at least one alumnus or student competing in every summer Olympics since 1972. In recent Olympics, up to two dozen Bolles students and alumni have swum for their respective countries. The Bolles Sharks, Bolles's club swim team, compete and practice year-round.
The school's football team is coached by Charles "Corky" Rogers, the all-time winningest Florida high school football coach, and has won eleven state championships, ten under Coach Rogers. For the 2009 season, the Bulldogs went 12-1, losing only to Cocoa High School, 44-37 in overtime. They defeated Tampa Catholic in the state championship game on December 12, 21-7.