Humphrey Gilbert was the first Englishman to make a serious proposal for settling a colony in North America. Queen Elizabeth finally granted him a charter in 1578. A dozen years earlier, he had drafted A Discourse of a Discoverie for a New Pasage to Cataia, proposing the exploration of the Northwest Passage to Cathay (China, or "Cataia"). However, his proposal was in conflict with the Muscovy Company's exclusive rights to trade between England and Russia.
The Muscovy Company had already searched for a Northeast Passage across the northern edge of Russia, to facilitate the fur trade between Europe and Siberia. Discovering a Northwest Passage to Russia might provide great benefit to England in general... but the stockholders of the Muscovy Company first wanted to be sure that they in particular would benefit. Their claim interfered with early proposals by other English capitalists to settle the eastern coast of North America, but that company also provided an economic model for the financing of the initial settlement in Virginia.
The Muscovy Company, chartered 50 years before the Virginia Company that financed settlement in Virginia, was the first joint-stock company in Elizabethan England. No single family could finance those high-risk explorations, but the joint-stock company allowed enterprising individuals to pool a portion of their capital and "adventure" those funds in hopes of getting rich. The kings and queens of England depended upon the private sector to finance the expansion of the country's economic and political power through discovery. In the United States today, however, inter-planetary space exploration is financed almost exclusively by the government rather than by venture capitalists who expect to make a profit.
Gilbert risked more than his money. He personally led the exploration to the New World in 1583, after a 1578 attempt was forced by bad weather to return almost immediately to England. Gilbert landed on Newfoundland, but no permanent base was established. He died when his ship disappeared on the return journey. His half-brother, Walter Ralegh, obtained a renewal of the charter or "Royal Patent " in 1584 and sought to settle a colony further south. Ralegh's last attempt to "plant" a colony on Roanoke Island in 1587, on what we now call the North Carolina coast, was also a failure. Those colonists disappeared, and the settlement is still described as the "Lost Colony."
By the time Jamestown was settled in 1607, the Europeans had the same sort of familiarity with the coastline of North America as we do today of the moon. Some areas they knew well from multiple visits, while other locations were totally unknown. There was no DeLorme Atlas and Gazetteer of Virginia sold in stores at that time, of course. Non-existent kingdoms where the streets were supposedly paved with gold, such as "El Dorado," and non-existent features were hypothesized either by over-optimistic explorers - or, if you prefer the cynical perspective, primarily to justify continued funding of their explorations. The explorations revealed the obvious characteristics of the land to the European visitors, but only year-round settlement would expose the skills and resources required for a colony to survive.