Complex sentence: He traveled to England on two occasions, in 1584 and 1585, and was among those who sailed for the New World in 1587 along with Governor John White and his colonists, who founded the failed settlement later known as "The Lost Colony".
Split into simpler sentences: He traveled to England on two occasions, in 1584 and 1585. After staying there, he was among those who sailed for the New World in 1587 along with Governor John White and his colonists, who founded the failed settlement later known as "The Lost Colony".