When some ninety-nine persons, led by Hugh O'Neill , Earl of Tyrone and Rory O'Donnell, Earl of Tyrconnell, sailed from Rathmullen County Donegal on 14 September 1607, it was destined to be probably the most momentous event in the history of the island of Ireland. The flight paved the way for the plantation of Ulster which introduced into that province Scots Presbyterians a sectarian division which still after four hundred years, defies the best efforts of the British and Irish governments to resolve.

Spain from where it was hoped a new expedition would be launched, was the destination of the Earls, but bad weather forced them to land in France, from where they headed towards Flanders, then a Spanish dependency. They wintered in Louvain where they heard the bitter news that Spain no longer wished to receive them. Eventually they were obliged to settle for Rome where they could expect little more than bulls and benedictions.

When they arrived in Rome they had covered almost 4,000 Kilometres, 1,200 at sea and the rest on horseback. The journey took them almost five and a half months passing through 109 towns, seven different countries, France , Spanish Flanders, Germany, the Swiss Cantons, the churches of Lorraine, Parma, Milan and the Papal State. The flight was to end in tragedy with the sudden deaths of Rory O'Donnell and his brother, Cuchonnacht Maguire, O'Neills son, the Baron of Dungannon and others, from malaria only a year after they left Ireland. O'Neill himself the last to survive, died in 1616, pleading in the end for help from Spain to return to Ireland at the head of an expedition but all in vain.