Born in 1692, Montague Garrard Drake was the son and heir of Montague Drake (MP of Shardeloes) and Jane Garrard (daughter of 3rd Baronet John Garrard). Drake matriculated at St John’s College, Oxford in 1706 aged only fifteen and was awarded an MA in 1709. Following his studies Drake embarked on a Grand Tour of Europe. Upon his return, he was unopposed as Conservative MP for Amersham in the 1713 general election, and was re-elected in 1715. In 1722 he decided to sit for Buckinghamshire until the constituents became exasperated with him and he returned to his Amersham seat in the 1727 election. In 1719 Drake had married Isabella Marshall (daughter of a merchant) and their son William was born in 1723. William would also go on to become an MP for Amersham.

Though the Grand Tour was becoming customary for young graduates, Drake’s trip is peculiar in that it began when he was eighteen, before he was considered to have come of age. On the first page of his diary Drake names his companions, Mr Osbaldeston and Mr Waddell. William Osbaldeston (1688-1766), son of Sir Richard Osbaldeston, became MP of Hunmanby in 1735. It is unlikely that Drake and Osbaldeston met at Oxford as Osbaldeston cannot be found in the Alumni Oxonienses 1500-1714. Richard Osbaldeston, William’s brother, graduated from St John’s College, Cambridge in 1714 and became a Fellow of Peterhouse, which could provide an explanation for how Drake’s travel diaries came to be located in Pembroke’s archives. George Waddell was a Scottish non-juring minister who travelled to Italy at least four times. Little information can be found on Waddell but considering his many returns to Europe it is possible he acted as chaperone to Drake and Osbaldeston.