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The monastery on Ynys Byr (Caldey Island) was founded around AD 525, by Pyr, a disciple of St. Illtud. The name Caldey is a Viking phrase meaning, 'Keld-ey' meaning Spring-Water Island.

Caldey's most famous son was St. Samson who became a monk here after leaving Llanilltud Fawr.  He was made its Abbot after the unexpected death of Pyr and instigated considerable reforms to the enclave during his three years in office.

The present monastic buildings date from the 11th century and include a fine modern stained glass window depicting St. Illtud and King Arthur.  Of chief interest to scholars of the Dark Ages is the so-called 'Caldey Stone' now affixed to the wall. It has bears an incised cross and has both an Ogam and a Latin inscription. The Ogam appears to say, "Magl Dubr" translated as 'Prince Dyfrig' and presumably referring to the great 6th century Bishop of Glywysing & Gwent, St. Dyfrig, who was wont to  spend lent on the Island. The Latin, however, may be a later addition as it reads, "And I have fashioned this with the Sign of the Cross of Jesus. I ask all who walk in this place to pray for the Soul of Cadwgan."

Today, there is also a modern monastery on Caldey, famous for its chocolate and perfume.