Kaja Castle was first mentioned in 1196. In the late 14th century it was conquered by robber barons Johann and Heinrich Leipa who spread the terror in the surrounding villages. The castle was again conquered by Hussites in 1425-1427. Later Kaja castle fell on decay, today it stands partly restored.
First record of Kastelholma (or Kastelholm) castle is from the year 1388 in the contract of Queen Margaret I of Denmark, where a large portion of the inheritance of Bo Jonsson Grip was given to the queen. The heyday of the castle was in the 15th and 16th centuries when it was administrated by Danish and Swedish kings and stewards of the realms. Kastelhoma was expanded and enhanced several times.
In the end of 16th century castle was owned by the previous queen Catherine Jagellon (Stenbock), an enemy of the King of Sweden Eric XIV. King Eric conquered Kastelholma in 1599 and all defending officers were taken to Turku and executed. The castle was damaged under the siege and it took 30 years to renovate it.
In 1634 Åland was joined with the County of Åbo and Björneborg and Kastelholma lost its administrative status.