Successfully establishing a viable colony for England in North America was a daunting undertaking. Plundering Spanish treasure ships when they returned to Europe from America was far easier. At the least, a colony in North America would give the English a naval base for use against its archenemy Spain. Sir Humphrey Gilbert (c. 1539—1583) had claimed Newfoundland for England in 1583, but his ship sank on its way back to England.

The next serious attempt at colonization was in 1587. After establishing the Roanoke colony in mid-1987, its governor, John White, sailed back to England. He had planned an immediate return, but a major war erupted with Spain. Upon returning in 1590, the English found the word CROATOAN carved on a tree. To this day, nobody knows what happened to the Roanoke colony.

Jamestown was founded in 1607 and it nearly failed, too. But Jamestown was fortunate because it received regular supplies by ship; it was not cut off from England for three years. In spite of this, the survivors decided to abandon the colony in 1610. As the weary colonists set sail for England in 1610, a relief force with supplies arrived.

In summary, the key difference between the two was that Roanoke did not get any help by ship, whereas Jamestown sometimes did.