William Strachey writes a long letter describing the voyage to Virginia on the Sea Venture to a lady in London, thought to be Lady Sara Smythe, wife of Sir Thomas Smythe, Treasurer of the Virginia Company of London and organizer of the details of the expeditions to Virginia. He starts by describing sailing from Plymouth Sound on June 2, 1609, and the ships keeping in sight of each other until St. James Day, Monday, July 24, 1609. He says that Captain Newport reckons they are only seven or eight days from Cape Henry on the Virginia coast at the time. Strachey relates that, starting the night before, Sunday night, “the clouds gathered thick upon us, and the winds singing and whistling most unusually” cause them to cast off the small unnamed ketch they are towing.
On May 23, 1609, King James I signs the second charter of the Virginia Company of London, updating it. Among other changes, the territory of the Virginia Company of London is now 200 miles north and south of Point Comfort on the Chesapeake Bay.
On May 5, 1609, the Virginia Company of London sends Captain Samuel Argall to Virginia to explore a more direct route to Virginia instead of going south along the coasts of Europe and Africa and then sailing west to the Caribbean and then north up the Gulf Stream along the Atlantic coast of America. The traditional southern route is the one John Rolfe and the Sea Venture will take ten days later.
The rationale for trying a more northern route is twofold. First, despite the peace treaty of 1604 between England and Spain, the Spanish are attacking English ships in the Caribbean. For example, in 1606, the Richard, a ship of the Virginia Company of Plymouth which holds the royal charter for more northern lands, sails the traditional route to the Americas and is then to head up to Pemaquid on the Maine coast north of the Kennebec River, but it is captured by a Spanish ship and all hands are sent to Spain and imprisoned. The second reason is to see if they can find a faster route to Virginia.
The Virginia Company of London proclaims that Protestant English colonization of America is God’s will. They get ministers to preach that God wants a Protestant English colony in Virginia rather than a Catholic Spanish colony like Mexico, most of South America and Central America, and St. Augustine in what is now Florida. The Virginia Company of London also preaches that it is God’s will to evangelize and convert the native savages of Virginia to the Protestant religion. So Rolfe’s goals are in line with what today are called the three G’s of colonization, Gold (literally or figuratively), Glory (of self and/or King and country), and God.
Rolfe takes care of the money or investment needed for every entrepreneurial venture by buying shares in the Virginia Company of London. He thereby secures passage to Virginia for himself and his wife, and land for planting in Virginia.
John Rolfe sees an opportunity, he identifies a market need that people will pay for, to break the Spanish monopoly of the mild tobacco the English prefer. Rolfe’s goal in traveling to Virginia is to grow the mild Spanish tobacco in Virginia, cure it, and export it to England at great profit, thereby bettering himself.