Surprisingly, of the 103 Mayflower passengers, only two are known to have had portraits made.  The first, and best authenticated, is the portrait of Edward Winslow.  The artist who painted the portrait is unknown, but the painting was done in London in 1651.  The original is currently in the possession of the Pilgrim Hall Museum in Plymouth, Massachusetts.  Edward Winslow came on the Mayflower at the age of 25, and was elected governor of Plymouth on several occasions, including 1633, 1636, and 1644.  Edward Winslow returned to England on colony business on several occasions as well, and in 1646 he returned to England permanently, where he took various positions in the government of Oliver Cromwell, following the English Civil War.  In 1651, he sat for the portrait, when he would have been 56-years old.  Three years later, he went as commissioner to the West Indies on an expedition to capture the island of Hispaniola.  He died at sea of a sudden fever, and was buried at sea between Hispaniola and Jamaica.

The other known portrait belongs to Myles Standish.  Standish was the militia captain at Plymouth, responsible for the colony's security and defense.  When he came on the Mayflower, he was in his mid-30s.  The portrait was "discovered" in a picture shop in Boston in 1877, so its authenticity has been debated.  The portrait was dated 1625, and was labeled "M. Standish," age 38.  The portrait's current owner or location is unknown--what exists are two late 19th century portraits that were based off the original.  From the two line drawings, noted portrait and maritime artist Mike Haywood, at my request, painted a full-color portrait of Myles Standish.