Key West's Islander Drive-in Made Famous by Jimmy Buffett

Drive-In’s were a big part of our lives from the 50’s to the 80’s, whether we were taking a date to smooch or sneaking through the gate in the trunk.

“In our old Chevy wagon we backed in so me and my brother could lay in the back with a blanket, buttered popcorn and a Coke. Years later on Friday nights we would take a date, with either Boones Farm country quencher or Mad Dog 20/20”. 

The Islander Drive-In was built by Joe Sirugo and opened on February 28, 1953 with “The Cimarron Kid” starring Audie Murphy, with the largest screen in Florida, and parking ramps for 650 cars with in car speakers. 

This was not your typical drive in theater since it was built on an island out over the water on Cow Key channel, where you could fish for snappers and groupers while watching the flick. In fact, there was a place in the back where you could fish from both sides of your car. Generations of kids learned math by counting fish and beer cans there. 

You can see why this place had a major influence on Jimmy Buffett’s life.

The Islander Drive-In lives on in Jimmy Buffett’s song “Grapefruit, Juicy Fruit”, which is about “committing a little mortal sin, it’s good for the soul” where they mixed up cheap Gilby’s gin with Welch’s grape juice to create “purple passions” and then had a good go at it. 

In fact, the drive in is even featured as the backdrop in his music video. “Take Another Road”.

You have got to remember this was Florida and on hot summer nights you had to keep the windows rolled up to fight the mosquitoes. 

As drive-ins declined in popularity, it was closed in 1984 and after sitting vacant for nearly two decades the property was redeveloped in the early 2000’s into Islander Village Townhomes.