The Island Boy
Rafael Antonio “Tony” Medina
Rafael Medina was born in Key West in 1979, the fifth generation of his family on the island.
His grandfather, Danny Acosta, was a sign painter — and the man who created the Southernmost Point Buoy, still the most photographed landmark in Key West. Rafael started painting at ten. He took the inspiration somewhere other than signs.
“Two things he taught me how to paint right away, palm trees and far away birds. And to this day, I’m painting palm trees and far away birds. They’re in every painting I do, just about.”
Surrounded by the land and seascapes of the Florida Keys, he painted what was in front of him — tropical scenery, island creatures, the people of Old Town. He was featured in local news and magazines while still young.
He is entirely self-taught. Without the years of technical training that usually build an artist, Rafael works with a natural command of composition, dimension, colour and light.
For years he sold paintings on the streets of Key West and at the nightly Sunset Celebration in Mallory Square, until demand outgrew what he could carry.
Later he pushed further, into abstract expressionism and the interactive pieces he is now known for — paintings that hide figures and faces inside the landscape, that reward the second look, that glow in the dark.
Today
Rafael’s work is carried by galleries and retailers across Key West and the mainland. The Island Boy Arts Studio Gallery sits in historic Old Town, where he paints live four to five days a week. The Island Boy Arts Fine Art Gallery at the Custom House Inn on Duval Street holds his most sought-after originals and limited editions.
In 2019 he showed in Wynwood, Miami during Art Basel. He has created four logos for the 7 Mile Bridge Run in Marathon, Florida. Keys Federal Credit Union features three of his paintings on their Visa cards — work that won Rafael and Keys FCU the National Diamond Award.
“Painting gives me ultimate joy, and the fact that it gives others that joy, too, makes us connected forever, we share the painting together, this is why I absolutely have to do this. It’s the connection.”