[4] His brother was Richard Drake (1535–1603) of Esher, an Equerry of the Stable and Groom of the Privy Chamber to Queen Elizabeth I and a Member of Parliament.
He did not participate in any overseas ventures, however, so far as is known, until 1585, by which time he had joined with Raleigh and Humphrey Gilbert's brother, John, in activities connected with the Roanoke Island Colony, in present-day North Carolina.
Teaming up with Raleigh-associate George Raymond, he took several Spanish traders around the Azores carrying sugar, wine and ivory, as well as a French vessel bearing gold.
A couple of months later, the surviving Portuguese prisoners, whom Drake had had imprisoned in Exeter Castle, were put on trial, the charge perhaps being mutiny.
Within little more than three weeks, the judge, eleven of the twelve jurors and eight justices of the peace, who had been exposed to the prisoners, died from an infection caught from the Portuguese.
A monument was erected by his son, John, in St. Michael's Church, Musbury, which shows three generations of family patriarchs at prayer, each kneeling with his wife.
He died the Xth of April 1586 and Dame Garthrud his wief was here bured the XIIth of Februarie 1601 unto the memorie of whome John Drake Esqr.