"[8] Though well-to-do in his own right through inheritances,[1][9] Henry tried one major business venture, traveling to live in Barbados to start a tobacco plantation,[1][4] but he was not successful.
[2][10][13][14] Eleven months after the marriage, Henry's father's flotilla of ships—the Winthrop Fleet—sailed west to create a "City on a Hill" in what would become the Massachusetts Bay Colony.
"[15] Henry was supposed to be in his father's lead ship, the Arbella, but he missed boarding due to helping to corral a herd of cattle.
"[18] With infant daughter Martha Johanna Winthrop in tow, Henry's widow Elizabeth sailed to the Massachusetts Bay Colony aboard the Lyon, arriving on 2 November 1631.
[19][21] Elizabeth would marry again to Lt. Robert Feake, and in the early 1640s, would move to an extensive property they acquired in Connecticut, encompassing what is now called Old Greenwich.
[22][23] Mary married John Willson "of Bedford, afterward of Rye,"[24] so their children continued the line of direct descent from Henry Winthrop in the American colonies.