John Rolfe departed England on the third supply fleet headed for the Jamestown Colony in May 1609. John Rolfe was a passenger on the flagship of this fleet, the "Sea Venture." John Rolfe was accompanied on this vessel by his wife, Sarah Hacker, and a small child named Bermuda. The "Sea Venture" was deliberately driven into the reef in Bermuda to prevent the ship from floundering. John Rolfe was in Bermuda (The Somers Isles, named after the Admiral of the Company, Sir George Somers) for ten months while two new ships were being built. Upon the completion of the ships, John Rolfe left Bermuda in May 1610, leaving behind his wife Sarah and the child Bermuda, who had both died. John Rolfe arrived in Jamestown on June 10, 1610 and began his work with tobacco.

John Rolfe departed England on the third supply fleet headed for the Jamestown Colony in May 1609. John Rolfe was a passenger on the flagship of this fleet, the "Sea Venture." John Rolfe was accompanied on this vessel by his wife, Sarah Hacker, and a small child named Bermuda. The "Sea Venture" was deliberately driven into the reef in Bermuda to prevent the ship from floundering. John Rolfe was in Bermuda (The Somers Isles, named after the Admiral of the Company, Sir George Somers) for ten months while two new ships were being built. Upon the completion of the ships, John Rolfe left Bermuda in May 1610, leaving behind his wife Sarah and the child Bermuda, who had both died. John Rolfe arrived in Jamestown on June 10, 1610 and began his work with tobacco.

John Rolfe obtained tobacco seeds from Trinidad and South America (even though Spain had declaired selling tobacco seeds to any non-Spaniard was punishable by death). The native Tobacco in Virginia was not liked by Europeans; so, Rolfe intoduced the seeds of the sweeter strains that he had somehow managed to acquire. In 1611, Rolfe is credited with being the first to commercially cultivate Nicotiana tabacum tobacco plants in North America; export of this sweeter tobacco beginning in 1612 helped turn the Virginia Colony into a profitable venture. Rolfe named his Virginia-grown strain of the tobacco "Orinoco", possibly in honor of tobacco-popularizer Sir Walter Raleigh's expeditions in the 1580s up the Orinoco River in Guiana in search of the legendary City of Gold, El Dorado. The appeal of Orinoco tobacco was in its nicotine, and the conviviality of its use in social situations.

John Rolfe obtained tobacco seeds from Trinidad and South America (even though Spain had declaired selling tobacco seeds to any non-Spaniard was punishable by death). The native Tobacco in Virginia was not liked by Europeans; so, Rolfe intoduced the seeds of the sweeter strains that he had somehow managed to acquire. In 1611, Rolfe is credited with being the first to commercially cultivate Nicotiana tabacum tobacco plants in North America; export of this sweeter tobacco beginning in 1612 helped turn the Virginia Colony into a profitable venture. Rolfe named his Virginia-grown strain of the tobacco "Orinoco", possibly in honor of tobacco-popularizer Sir Walter Raleigh's expeditions in the 1580s up the Orinoco River in Guiana in search of the legendary City of Gold, El Dorado. The appeal of Orinoco tobacco was in its nicotine, and the conviviality of its use in social situations.

In 1612, Rolfe established Varina Farms, a plantation on the James River about 30 miles (48 km) upstream from the Jamestown Settlement, and across the river from Sir Thomas Dale's progressive development at Henricus.