The Winthrop Fleet was a group of 11 ships led by John Winthrop out of a total of 16 funded by the Massachusetts Bay Company which together carried between 700 and 1,000 Puritans plus livestock and provisions from England to New England over the summer of 1630, during the first period of the Great Migration.

John Winthrop was an English Puritan lawyer and a leading figure in the founding of the Massachusetts Bay Colony, the second major settlement in New England following Plymouth Colony. Winthrop led the first large wave of colonists from England in 1630 and served as governor for 12 of the colony's first 20 years. His writings and vision of the colony as a Puritan "city upon a hill" dominated New England colonial development, influencing the governments and religions of neighboring colonies in addition to those of Massachusetts.