Wihtwara was named, supposedly, after Wihtgar who, along with Stuf, was one of the two earliest kings of Wihtwara (recorded by St Bede in 512). Wihtgar and Stuf were supposedly nephews of Cerdic, the founder of the Wessex dynasty known only as the Gewisse (literally "Allies"). Some scholars have suggested that Wihtgar may have been fictitious: that is, the central figure of a founding myth invented retrospectively, to justify the name. The Anglo-Saxon Chronicle differs, however, instead claiming that Wihtgar and Stuf received the land from Cerdic's son Cynric in 534, with the death of Wihtgar taking place in 544. Subsequent kings are unknown until the final Jutish king, Arwald, who was probably born in the mid 7th Century. In 661 Wulfhere of Mercia conquered Wessex and gave the overlordship to his godson, King Aethelwalh of Sussex and forced the Islanders to convert to Christianity. After Wulfhere's departure the island returned to paganism. Arwald was reportedly killed resisting an invasion in 686 by King Caedwalla of Wessex (under the tutelage of St Wilfrid) together with his brother Mul of Kent. According to Bede, Caedwalla "endeavoured to destroy all the inhabitants" of Wihtwara and to replace them with his own followers. When Caedwalla died a few years later, wounds sustained in the fierce fighting at Wihtwara were reputedly responsible. The only recorded survivor from the alleged massacres at Wihtwara was Arwald's sister (whose name is now unknown); through her its ruling dynasty became ancestors of later Anglo-Saxon kings. Arwald's sister was married to King Egbert of Kent (at the time also a Jutish kingdom besieged by Caedwalla and his brother, Mul). Arwald's sister was therefore, apparently, the mother of King Wihtred of Kent and grandmother of Æthelbert II of Kent. Æthelbert was the grandfather of Egbert of Wessex, who was, in turn, the paternal grandfather of King Alfred the Great.

After the Norman Conquest the Isle of Wight was given to the de Redvers family in 1101 who were known as "Lords of the Isle of Wight". However the last of them was Izabel de Forz (also known as Isabella de Fortibus; 1237–1293), who was known informally as the "Queen of the Isle of Wight". Forz was visited shortly before her death by King Edward Longshanks (known later as Edward I), who said later that she had sold the Isle of Wight to him for 6,000 marks. The village of Queens Bower is said to be named after her. In 1444, Henry Beauchamp, Duke of Warwick a favourite of King Henry VI was given the title (or perhaps nickname) of King of the Isle of Wight. Beauchamp died shortly afterwards and the title was not used again. The closest existing title at that time - the Lordship of the Isle of Wight - was held by the uncle of King Henry VI, Humphrey, Duke of Gloucester, after being bestowed it in 1434.