There are several theories about the island’s name, from claims of pre-Slavic origins, to the suggestion that Šipan is derived from the Greek word “gypana”, meaning “falcon’s nest”. In any case, the island’s modern name was first documented as early as 1371. In the Port of Šipan, the remains of a Roman villae rusticae can be found, but most of the traces of earlier life and historic architectural monuments there date from the Medieval Era.
Šipan has 34 churches, six of which are pre-Romanesque, a late-Gothic Rector's Palace and the ruins of archbishop's palaces that were built for the Bishop of Dubrovnik - the famous Italian writer, poet and theologian from the mid-16th century Lodovico Beccadelli. Among its ruins can be seen the remains of a stone frieze of portraits, one of which is the work of Michelangelo.
St. Marija’s church in Pakljena, built in the 13th century, was a well known Templars’ shelter, a monastic order that disappeared during the 14th century. The Templars there were directly involved with Rene Renato d’ Angio, who was banished in order to prevent him from becoming a king. In the village of Renatovo are the ruins of a small castle, believed to be Rene’s residence during the 15th century, where an emblem with an inscription Renatus rex justus was found.
Šipan is home to many beautiful 16th Century villas built by Dubrovnik’s nobility, which were meticulously designed in such a way as to be integrated with the surrounding landscape, as well as grand stone buildings built by wealthy merchants and sailors who were originally from the island.
The Sorkočević family, quite well known in their time, built a summer residence in Šipan’s main port during the 15th century which remains to this day.
The building of the Skočibuha family castle, which still dominates the town of Suđurađ, began in February 1563 and ended in December of the same year. The castle interior has a large square Renaissance fireplace with a nicely preserved plaster-decorated hood (which was an exception in the Dubrovnik area), an elegant Renaissance stone sink with reliefs decorating its edges and a rare example of the only preserved wooden balcony in the Mediterranean dating from the 16th century.
On a lighter note, Šipan is included in the Guiness book of records as the island with the greatest ratio of olive trees to human inhabitants considering its total surface area.