Raleigh would have liked to go on the Virginia voyage himself, but had to be content with sending Grenville as Admiral of the Fleet, and Ralph Lane to be Governor of the proposed colony.
The latter was a Northamptonshire man, second cousin to Queen Katherine Parr, about ten years older than Grenville, and one of Leicester's band of equerries to the Queen.
They sailed in April, 1585, from Plymouth with seven vessels, the largest being of 140 tons burthen. Thomas Cavendish was one of their number. Sailing by way of the Canaries to the West Indian Islands, they anchored in Mosquito Bay, in the island of Puerto Rico, within falcon-shot of the shore.
Sir Richard landed and gave orders for a fort to be built in an angle between the river and the sea, backed by woods. There he remained some days, felling the timber and building a pinnace, the Spaniards looking on from afar.
After some days a party of twenty horsemen showed themselves on the opposite bank of the river, carrying a flag of truce; two from either side met on the sands and discussed politely and courteously. When the Spaniards expressed some surprise at the English having built a fort in Spanish territory, they were told that it was only to procure water and food, which if they could not get by fair means, it was their resolution to win by the sword.
Upon this discreet answer the Spaniards made "large promises of all courtesy."
On the morrow, the pinnace being finished, Sir Richard marched some four miles up country, awaiting the Spaniards' performance of their promise to bring victuals. As they did not come up in time—what Spaniard ever does?—Sir Richard swore a little, called them perjured caitiffs, and fired the woods and his fort. Setting sail, he took next evening a Spanish frigate, which the Spaniards forsook at the sight of his squadron. The next night he captured another "with good and rich freight, and divers persons of account in her," whom he ransomed for good round sums.
One of these prizes was sent to Roxo Bay, where Ralph Lane built a fort, while the others busied themselves in stealing a shipload of salt from the Spaniards. After this they sailed for Hispaniola and anchored at Isabella.
The Spanish Governor came to the seaside to meet Grenville, each being very polite and very suspicious of the other; but polite demeanour prevailed. The English provided two banqueting houses, covered with green boughs—one for the gentlemen, the other for the servants; a sumptuous feast was brought in, served all on plate, while the drums and trumpets played lively music, wherewith the Spaniards were vastly delighted.
In return, the Spaniards sent for a great herd of white bulls from the mountains, and lent to each gentleman and captain a horse ready saddled, and then singled three of the strongest of the herd to be hunted.