Cubbie Roo's Castle, built about 1150, is one of the oldest castles in Scotland and was mentioned in the Orkneyinga Saga. It takes its name from Kolbein Hruga who was said to have lived there. In King Haakon's saga, it is mentioned that after the last Norse Earl of Orkney, Earl John, was murdered in Thurso, his killers fled to Wyre. They took refuge in the castle, which was so strong that the besiegers had to thrash out a deal with them to get them out.
References:Herceg Novi was founded (on a former small fishing village, existing since Roman Empire times) as a fortress in 1382 by first Bosnian King Stjepan Tvrtko I and was called Sveti Stefan or Castelnuovo. The Turks conquered Herceg Novi in 1482, and ruled for 200 years, until 1687. However, there was a short pause between 1538 and 1539 when it was held by the Spaniards before they were defeated in the Siege of Castelnuovo. Turkey ruled again until 1687, from then until 1797, the town was ruled by the Venetian Republic.
The Herceg Novi old town is amazing. It is on a fairly steep hill that leads all the way down to the sea. Wandering through the small stairways to the various plazas and fortresses is a many hour adventure.