Bonnie Prince Charlie and the The Outer Hebrides aren’t immediately synonymous.

Culloden, his cosseted lifestyle, and his disputed claim to the British Throne usually feature first.

But the islands were pivotal in the fortunes of our romantic rebel.

So let’s retrace his Hebridean steps, in Jacobite sized chunks.

The Young Pretender

Born Charles Edward Louis John Casimir Sylvester Severino Maria Stuart on the 20th of December 1720, Bonnie Prince Charlie spent his early years in aristocratic Rome. 

His childhood was pampered but unhappy - he saw more of his maids than his parents, and was deeply affected by their acrimonious divorce. 

So he grew into a clever yet hot-tempered young nobleman, desperate for any opportunity to prove himself…


After a failed invasion in 1744, Bonnie Prince Charlie travelled to Scotland to reclaim the British throne. 

He landed on Eriskay, South Uist on the 23rd of July 1745 at a point now known as Prince’s Beach, before heading to the mainland.

Doomed Rebellion

Bonnie Prince Charlie sought highland soldiers. 

He went from clan to clan, finding some, but hardly legions sympathetic to his cause - once they realised he had few troops, fewer weapons and only a miserly amount of cash.

Despite some victories, Bonnie Prince Charlie’s progress was halted, still over 100 miles short of London. 

His involvement ended in a bloody, blundering defeat at Culloden. He escaped uninjured, but with a £30,000 bounty on his head.

Hebridean Hideout

“Speed bonnie boat like a bird on the wing. Onward the sailors cry.

Carry the lad that’s born to be king over the sea to Skye.”

It could be because the South Uist Clan Ranald had heavily supported the Jacobite cause that Bonnie Prince Charlie chose to return there after Culloden. 

Or maybe he’d scouted hundreds of hidey-holes when he first arrived in the Outer Hebrides.

Either way, Charlie spent months criss-crossing the islands, visiting places like Scalpay and Stornoway, ruthlessly pursued by government forces, before fate intervened.

Flora MacDonald took a trip to Benbecula. 

Flora’s stepfather ran the pro-government militia in Benbecula, and in an ironic twist, had never joined the rebellion.

And in another twist, one of Bonnie Prince Charlie’s companions, Captain Conn O'Neill, was distantly related to Flora. When he learned of her whereabouts, he reached out for help.

A legendary getaway was afoot.

Flora hoodwinked her stepfather to secure her group’s passage back to Skye, only this time Bonnie Prince Charlie joined them, disguised as an Irish maid called Betty Burke.

These clandestine scenes later inspired the iconic Skye Boat Song with its famous refrain, ‘Over the Sea to Skye’

Once safely deposited - Bonnie Prince Charlie travelled on, eventually returning to France. Flora was arrested and imprisoned in the Tower of London, before being released one year later.

Plan Your Escape

What followed wasn’t pleasant. For highland culture or the man himself. 

But let’s not dwell.

Escaping to the Outer Hebrides saved Bonnie Prince Charlie’s life. 

When you visit - you might just feel the same.

Follow our Bonnie Prince Charlie Trail to find out more.