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The strategic importance of the Island substantially increased with the development of Portsmouth as a permanent naval base. Henry VIII accordingly built additional fortifications on the island at Yarmouth, East & West Cowes and Sandown, sometimes re-using stone from dissolved monasteries as building material. Sir Richard Worsley, Captain of the Island at this time, successfully commanded the resistance to the last of the French attacks in 1545, at the time of the loss of the Mary Rose.

During the reign of Elizabeth 1, the Island was again threatened by invasion, this time from Spain. Sir George Carey, cousin of the Queen and Captain of the Island, took up residence at Carisbrooke Castle in 1583 and undertook repairs to the defences. Although the Armada was defeated in 1588, the Spanish threat remained, and the outer fortifications of Carisbrooke Castle were built between 1597 and 1602 in response to the invasion scare.

At the outset of the Civil War in 1642, the Parliament assumed control of the Island and retained their control throughout the conflict. In spite of this, King Charles 1 went to the Island on escaping from imprisonment at Hampton Court in November 1647. As a prisoner at Carisbrooke Castle, the King made several unsuccessful attempts to escape before being transferred to Newport in September 1648, where abortive negotiations with Parliament (known as the Treaty of Newport) took place. In November, the King was seized by the Army and taken to Hurst Castle and then to his trial and execution in London.

In the nineteenth century the Island was transformed by the coming of the railways. Queen Victoria took advantage of the island's new accessibility by using Osborne as her retreat. Affairs of the state soon followed her and the modestly furnished family home had to be enhanced with apartments where she could receive foreign heads of state. However, her children enjoyed many hours and a great deal of freedom at Osborne as a visit to Swiss Cottage will indicate. Queen Victoria's affection for Osborne added to the Island's attractions of climate and scenery, and Ryde, Sandown, Shanklin & Ventnor expanded from fishing villages to fashionable resorts.

Queen Victoria's youngest daughter, Princess Beatrice, succeeded her husband, Prince Henry of Battenburg as Governor of the Island in 1896, and regularly used Carisbrooke Castle as her summer residence. After her death in 1944 the office was left vacant until, at the request of the Island, a new Governor was appointed in 1957 - the seventh Duke of Wellington. He was succeeded in 1965 by Admiral of the Fleet, the Earl Mountbatten of Burma, a great nephew of Princess Beatrice. When the Island gained full County status under the Local Government Act in 1972, Earl Mountbatten was appointed the Island's first Lord Lieutenant as well. Since his death in Ireland in 1979, the Island has been without a governor.