One Crazy Summer (1986)
In this cheesy 80s comedy, an aspiring cartoonist named Hoops McCann (John Cusack) goes with his best friend (Joel Murray) to Nantucket for the summer where he meets a young singer (Demi Moore) and must compete in a sailing regatta to win back her grandparents' house from greedy land developers. Much of the filming was done around Falmouth, MA with a few scenes shot on Nantucket Island.
The high school graduation scene was filmed outside the old Barnstable High School which is now Pope John Paul II High School at 120 High School Road in Hyannis Port, MA.
GPS Coordinates:
41.648401,-70.2846
"Generic Elementary School" is actually Hyannis West Elementary School at 549 West Main Street in Hyannis Port, MA.
GPS Coordinates:
41.650349,-70.316196
The car jump onto the ferry was filmed at the Woods Hole ferry dock which actually goes to Martha's Vineyard.
GPS Coordinates:
41.522222,-70.670025
The exterior of "Raymond's Army/Navy Store" where General Raymond (Joe Flaherty) works is now The Sunken Ship at 12 Broad Street on Nantucket.
Taylor (Taylor Negron) and Wilbur (Rich Hall) work at Mid-Way Garage at 981 Main Street in Osterville, MA which still looks very much the same today.
Hoops is seen passing out flyers at the corner of Main Street & Orange Street in Nantucket.
GPS Coordinates:
41.283088,-70.099252
The regatta starts and ends at Sesuit Harbor in East Dennis, MA.
GPS Coordinates:
41.757387,-70.154867
Google Map
(See attachment below)