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Oracabessa is a small town in St Mary, Jamaica 10 miles (16 km) east of Ocho Rios. Its population was 4,108 in 2009.

Lit in the afternoons by an apricot light that may have inspired its Spanish name Oracabeza, or “Golden Head”, it is a friendly town with a covered produce market and a few shops and bars. The main street is a pleasant and graceful promenade with a number of well-maintained buildings in the early 20th century Jamaican vernacular tradition. To the immediate west of Oracabessa is the village of Boscobel, home of Ian Fleming International Airport, Jamaica’s newest international airport.

One of Oracabessa’s most well-known residents is artist Richard Von White, grandson of W.E. White a self-made man, baker, planter and Oracabessa’s leading citizen in the early 1900s. Von’s brilliantly hued, evocative canvasses reflect the tropical flora that is the source of his inspiration. Other notable residents of Oracabessa include legendary music producer Chris Blackwell and bestselling author Colin Simpson. Blackwell owns Goldeneye villa, original home of author Ian Fleming, who wrote many of the James Bond novels while living in Oracabessa. Simpson owns Golden Clouds villa and is the great-great grandson of renowned slavery abolitionist James Phillippo.

The history of Oracabessa dates back over 500 years to the year 1502 when Christopher Columbus sailed into Oracabessa Bay, and bestowed the name Santa Maria island on the idyllic island located in what is now Goldeneye estate. At the time, the area was populated by a small number of Taino and Arawak Indians and the Spanish established a small supply post named Oracabeza, or “Golden Head” for the magnificent sunsets viewed from the cliffs of the colony. Oracabessa remained a Spanish settlement until 1655, when the British captured the North Coast of the island.

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