The Flight of the Earls refers to the day of September 14, 1607 when Hugh O’Neill and Rory O’Donnell left Ireland for exile in Spain.
A decade earlier, in a final attempt by the old order to reverse the tide of English power, an army had been organised by Hugh O'Neill, chief of Tir Eoghain, and Red Hugh O'Donnell, beginning a series of battles with the English which came to be known as the Nine Years War. After losing the battle of Kinsale, and waiting in vain for assistance from the Spanish Armada, O' Neill and O' Donnell had no hope of prevailing against the English and made their way to Spain. In fact, stormy weather prevented them from reaching Spain - they made landfall in France, precipitating a diplomatic crisis among the English, French, and Spanish governments. As a compromise, the Earls took up residence in Rome, where they died several years later.
The departure of O' Neill and O' Donnell was one of the immediate contributing factors leading to the Plantation of Ulster in 1608.