He dared the extremity of his political fortunes by writing on a pane of glass which the queen must see, "Fain would I climb, but fear I to fall." And she replied with an encouraging--"If thy heart fail thee, climb not at all." The queen's favor developed into magnificent gifts of riches and honor, and Raleigh received various monopolies, many forfeited estates, and appointments as lord warden of the stannaries, lieutenant of the county of Cornwall, vice-admiral of Cornwall and Devon, and captain of the queen's guard.
The manner in which Raleigh went about the work of colonization showed remarkable forethought and system.

In order to enlist the active cooperation of the court and gentry, he induced Richard Hakluyt to write for him, in 1584, his _Discourse on Western Planting_, which he circulated in manuscript.[5] He not only received from the queen in 1584 a patent similar to Gilbert's,[6] but by obtaining a confirmation from Parliament in 1585 he acquired a national sanction which Gilbert's did not possess.[7] In imitation of Gilbert he sent out first an exploring expedition commanded by Arthur Barlow and Philip Amidas; but, warned by his brother's experience, he directed them to go southward.

They left the west of England April 27, 1584, and arrived upon the coast of North Carolina July 4, where they passed into Ocracoke Inlet south of Cape Hatteras.

There, landing on an island called Wokokon--part of the broken outer coast--Barlow and Amidas took possession in the right of the queen and Sir Walter Raleigh.[8] Several weeks were spent in exploring Pamlico Sound, which they found dotted with many small islands, the largest of which, sixteen miles long, called by the Indians Roanoke Island, was fifty miles north of Wokokon.

About the middle of September, 1584, they returned to England and reported as the name of the new country "Wincondacoa," which the Indians at Wokokon had cried when they saw the white men, meaning "What pretty clothes you wear!" The queen, however, was proud of the new discovery, and suggested that it should be called, in honor of herself, "Virginia." Pleased at the report of his captains, Sir Walter displayed great energy in making ready a fleet of seven ships, which sailed from Plymouth April 9, 1585.