War with Spain had become official, and the crown desired that all ships be made available for naval warfare, for the Spanish Armada was extensive and formidable. Eventually, the queen allowed for two small ships to be dispatched to relieve the colonists, but in 1588, when sailing under the authority of the crown, captains of even smaller ships apparently could not resist the siren call of the sweet trade, and therefore engaged in piracy, or privateering as it was called when sailing under the auspices of a king or queen. The ship carrying Governor White seemed in no hurry to get him back to his family, for its captain set about preying on vulnerable ships throughout European waters, and eventually his ship fell prey itself, suffering a cannon volley and being boarded by the French. Reportedly brutal fighting took place upon her decks, and Governor White was lucky to have survived. Eventually, the ship returned to England, as did the other ship dispatched to bring the colonists aid.

The Anglo-Spanish War raged on throughout that year, and indeed the Spanish, at one point in 1588, reconnoitered the island of Roanoke and saw the British fort and settlement, seemingly still intact and inhabited. They planned to return and attack the colony but, as far as Spanish historical records show, never actually did so.

Meanwhile, back in Britain, White struggled to put a new fleet together. Even after the war was officially won, merchant ships were held in port against Spanish attack. Not until 1590 did White manage to get permission for a merchant privateer to carry him back to the colony, and even then the merchantman who owned the fleet refused to take any other passengers or even any supplies, as his chief interest was the taking of ships and cargo as prizes while abroad.

It had, however, been two and a half years since White had seen his daughter or granddaughter, and it is therefore understandable why he would take any opportunity to reach them, even if it meant returning alone and empty-handed. After crossing the Atlantic, the merchant fleet spent months in the Caribbean, privateering, and one can only imagine the impatience and frustration White must have felt: the longest leg of his journey complete and once again back in the New World, and they tarried south of Florida, occupying themselves with their depredations.

Finally, almost five months after leaving England, they reached Virginia and the island of Roanoke. The waters they had to cross in boats were tumultuous, and one of the fleet’s captains drowned with six other men when their boat overturned. White and others in two boats approached at night, saw a distant light and rowed toward it, blowing a trumpet and singing in English to announce their arrival in the darkness. They heard no reply. In the morning, they found that the light they’d seen had actually been a number of trees that had mysteriously been set on fire. They crossed through the burning forest and followed the beach to the settlement White had left in 1587, and as they crested a hill to approach the colony, they found a tree the letters “CRO” carved into it. On to the settlement then, and they found a palisade of tree trunks that had been placed as posts to form a wall around the dwellings, a fortification against some danger, but the dwelling places themselves, within the walls had been dismantled, and there was no sign of the settlers. One can imagine White calling out, shouting for Eleanor and Ananias, for little Virginia Dare, and receiving no answer.

They searched the settlement. Finding no one, White sought out some chests that he had buried 3 years earlier and found them exhumed, ransacked, their contents, including his maps and artwork, spread over the ground. Continuing his search, likely in mounting desperation, he looked for some sign, an indication of what might have happened to the settlers and his family. Before White departed in 1587, arrangements had been made for the colonists to leave a sign if they decided to or were in some wise forced to move inland: a Maltese cross was to be carved somewhere as a message. Eventually, a clue was discovered. On a post in the palisade, the word CROATOAN had been carved, but no Maltese cross.