A letter from Mary Queen of Scots to the French ambassador in England is up for live auction next month.
The appeal from Mary to let Scottish nobleman, George Douglas safely enter France is in her own handwriting and has been estimated to raise £14,000-£18,000.
Mary wrote it in Carlisle Castle two months after she managed to escape from Lochleven Castle in Perthshire on May 2 1568.
She had to abdicate in favour of her baby son James VI just two months before and had been imprisoned in the castle for nearly a year.
Mary was hoping George Douglas would help to secure her freedom by interceding with the French king on her behalf.
Lyon and Turnbull will auction the one-of-a-kind letter on Wednesday February 2.
Cathy Marsden - their rare books, manuscripts and maps specialist - said: "It is rare for a document with Mary’s handwriting to come up for auction. Having custody of this fragile letter is quite special.
“There are 12 lines written by a secretary, and (an) additional six lines in Mary’s own hand.
"The letter is signed, ‘Votre bien bonne amye, Marie’, which translates as ‘Your very good friend, Mary’.
“Given Mary’s unique place in history, we anticipate a lot of interest in this sale.”
The detail in the letter requests the French ambassador to Queen Elizabeth I to lend George Douglas, the bearer, 300 ecus (gold coins) and negotiate with the French royal family to secure a trouble free passage for George.
Mary managed to escape from Lochleven with the aide of George Douglas and his cousin, William Douglas.
She was later imprisoned by Queen Elizabeth I for 19 years before being beheaded at the age of 44 in Fotheringhay Castle, Northamptonshire on February 8 1587.
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