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The municipality of Ceglie Messapica is halfway between Brindisi and Taranto, close to Ostuni and Martina Franca.
It was founded by the Messapians in the pre-Roman period, but its history is controversial. According to Herodotus, the founder was Japige, king of Crete, who named it Kailìa, while other authors attribute the name to the Pelasgians, a people from the East, who built the city walls and called them Specchie. The temples of Apollo and Venus were famous as a pilgrimage destination. It was the military capital of Messapia and fought vicious commercial and political wars with nearby Taranto. Upon its decline it was subjugated first to the Romans and then in the medieval period to the Longobards, who gave it the name Geglie del Gualdo.
Under the Spanish it became a centre of secondary importance. Later it was part of various baronages. For a time, it belonged to the Archbishops of Brindisi.
When Count Sanseverino took it over, the castle and its walls were extended. A Collegiate church and a few convents were also built.
During the Renaissance, it became part of the Kingdom of Italy, and saw a period of prosperity which made the construction of numerous works and monuments possible.