In June 1746, Flora MacDonald, a 24-year-old woman staying on the Outer Hebridean island of Benbecula, set sail over the sea towards Skye. She travelled with several companions, including an Irish spinning maid whom the party called ‘Betty Burke’. Dressed in a calico gown, quilted petticoat and headdress, ‘Betty’ was in fact Prince Charles Edward Stuart, the figure known to history as Bonnie Prince Charlie, and Flora was risking her life to sail him to safety.


The second Jacobite uprising, popularly known as the ’45, had suffered its death knell at the battle of Culloden a few months earlier. On 16 April 1746, forces of the Duke of Cumberland had crushed the Jacobite army, bringing to an end the attempts to install Charles as a Catholic monarch of Scotland. Following the battle, and with his remaining supporters imprisoned or dispersed, the ‘Young Pretender’ fled for his life with a bounty of £30,000 on his head. He travelled about the Highlands in hiding, evading capture while seeking to escape abroad, and soon his manoeuvres took him to the Outer Hebrides.

Flora MacDonald (born 1722) might have seemed an unlikely ally – both her stepfather, Hugh MacDonald, and Allan MacDonald, the man to whom she was betrothed, were serving in the army of Hanoverian King George II. Yet a companion of the prince, one Captain O’Neill, had heard of Hugh, and that he harboured some Jacobite sympathies. Through O’Neill and her stepfather, word reached Flora that the Young Pretender sought help. Though she initially hesitated, she eventually agreed to aid the royal. A plan was laid that the prince would join her to sail “in Woman’s cloathes [clothes], as her servant”, and that she would “furnish cloathes for the young Pretender, as her own would be too little”.

The escape of Bonnie Prince Charlie

Using her family’s connections to the local militia, Flora secured permits for herself and her companions – the prince, O’Neill, and a crew of six men – and on 27 June 1746 they set sail for Skye. Landing on the island’s north peninsula at a place that is now called Prince’s Point, they travelled to the main town of Portree where arrangements were made for Charles to be picked up by a French warship. According to one story, Bonnie Prince Charlie gifted Flora a locket as they parted – sparking the suggestion in later years that it was a romantic gesture.

Bonnie Prince Charlie and Flora MacDonald
One story has Bonnie Prince Charlie presenting Flora with a locket as they parted. (Photo by The Print Collector/Getty Images)

However, no evidence exists to show that the pair were lovers or, indeed, had anything more than a fleeting encounter as she aided the prince and his men. Whatever their connection, Flora’s actions meant that within a few months of his journey to Skye, the Young Pretender had finally made his escape to safety.

More like this

Two weeks after making their journey, Bonnie Prince Charlie’s flight from Benbecula was discovered by English forces and, upon questioning of the boatmen, Flora MacDonald’s involvement was revealed. She was arrested and imprisoned, first at Dunstaffnage Castle in Oban and then briefly in the Tower of London. However, Flora’s impeccable behaviour during imprisonment earned her great respect. In an October 1746 letter, Earl Albemarle, who had served at Culloden under the Duke of Cumberland, wrote to the Secretary of State: “Her behaviour has been such during her Confinement, that Commodore Smith and General Campbell begs of your Grace, that when she arrives she may rather be put into the hands of a Messenger, than into any common Prison, this favour the poor Girl deserves, her modest behaviour having gained her many friends.”

According to one anecdote, Flora was later questioned by Prince Frederick, the son of George II, as to why she had helped the Pretender to escape. She is reported to have replied: “It was no more than I would have done for your majesty, had you been in like situation.”

This attitude, along with support from the public, led to Flora’s release in 1747. She returned to Scotland and married Allan MacDonald of Kingsburgh in 1750.

Flora’s role in Charles’s escape had ensured her legacy as a Jacobite heroine. In 1773, she was visited by literary duo Samuel Johnson and James Boswell on their famous tour of the Highlands and Islands. They concluded she was “a little woman, of a genteel appearance, and uncommonly mild and well bred”. However, that’s not the end of Flora’s story.

Flora MacDonald and North Carolina

In 1774, with her family in debt and their future uncertain, Flora emigrated with her husband and their children to the British colony of North Carolina. “Thousands of Highlanders,” writes Professor James Hunter for HistoryExtra, “mostly hard-pressed agriculturalists in search of land of the sort made available by North Carolina’s colonial administration to people willing to clear and cultivate it, had already made the same journey.”

There, in the country of the Cape Fear River, they purchased an established plantation and accompanying house, and quickly became embroiled in the politics of the colonies’ fight for independence. But, where Flora had once aided a cause in direct conflict with the British crown, this time she would be firmly allied with the royal cause. In 1776, as her new husband recruited fighters – many of them fellow Highlander emigrees – on behalf of the British government, Flora, it is said, pronounced a Gaelic blessing on the men. “She made a powerful address,” wrote JP McClean in his 2016 book The Two Lives of Flora MacDonald, “with all her power, exhibiting her genius she dwelt at length upon the loyalty of the Scotch, their bravery, and the sacrifices her people had made. She urged them to duty.”

Allan MacDonald served at the ensuing battle at Moore’s Creek near Wilmington in North Carolina in 1776, where the loyalists’ charge was cut down by heavy musket fire. More than 850 soldiers were taken prisoner in an easy victory for the North Carolina Patriots; Allan himself was taken into custody and the MacDonalds’ property was seized. Flora returned to Scotland in 1779, later joined by her husband after America won its independence in 1783.

An inscription on the monument marking the grave of Jacobite heroine Flora MacDonald
An inscription on the monument marking the grave of Jacobite heroine Flora MacDonald. (Photo By RDImages/Epics/Getty Images)

Flora MacDonald died in Skye in 1790, at the age of 68. Her grave can be seen today not far from the place where she is thought to have landed with the Young Pretender nearly 45 years earlier. In a final nod to the act that secured her name in history, legend has it that Flora was buried in a shroud formed of a bedsheet once used by Bonnie Prince Charlie.

Some have spotted parallels between Flora’s story and that of Claire Fraser in Diana Gabaldon’s hit series of Outlander novels. Indeed, there are many elements of Claire’s story that mirror Flora’s life; for instance, both are caught up in the Jacobite cause in 18th-century Scotland and later emigrate to the British frontier colony of North Carolina, where they are swept up in events that lead to the American Revolution. The television adaptation of Outlander even borrows its theme song from the 19th-century ‘Skye Boat Song’, which includes lyrics inspired by Flora’s actions to save the prince.

“Speed bonnie boat like a bird on a wing,
Onward the sailors cry.
Carry the lad that’s born to be King,
Over the sea to Skye.”


As well as being cited as a possible inspiration for Claire’s character, Flora MacDonald herself appears later in the book series, rallying loyalist troops to fight against patriots in the early days of the American Revolution.


Elinor EvansDigital editor

Elinor Evans is digital editor of She commissions and writes history articles for the website, and regularly interviews historians for the award-winning HistoryExtra podcast