Early European settlements in the islands were tenuous. The Virgin Islands, like the rest of the Caribbean, were the stage for European battles for supremacy. Alliances and enemies changed quickly; depending on your perspective, marauding ships were either pirate or patriot. Disease, war, and economic uncertainty made life difficult and unpredictable.

From 1493 until the late 1500s, settlements in the Virgin Islands were actively discouraged by the Spanish, who had established a colony on nearby Puerto Rico. Some historians say that the Spanish established a small mining outpost on Virgin Gorda in the first half of the 16th century, further discouraging other European powers.

By the beginning of the 17th century Spanish supremacy was fading, and other European powers grew intent on settling the islands. There is evidence of Dutch and English settlements on St. Croix as early as 1625. In the British Virgin Islands, there are records of English settlements in 1640 and 1646, and a French settlement in 1648. Early settlers were a hardy bunch, drawn by the lure of adventure, possibility of profits, and, in some cases, desperation.