Prince Rupert of the Rhine: Pirate Prince of the Caribbean #17thCentury #StuartAge

By Unidentified painter – Public Domain

One of the most dashing and iconic figures of the War of the Three Kingdoms is Prince Rupert of the Rhine. The son of Frederick V, Elector of Palatine, and Elizabeth Stuart, daughter of King James VI of England, he fought for King Charles I’s against Parliament. The force and swiftness of his cavalry charge usually struck terror in the Parliamentarians (although it could have been more disciplined). To this day, portraits of Rupert still causes hearts to flutter. 

While Rupert is mostly known as a Royalist cavalry commander, he did enjoy a brief sojourn as a Pirate Prince, sailing through the West Indies with his fleet, capturing Parliamentarian ships as prizes.

One of the perks of setting Severed Knot in the Caribbean was the opportunity to include Prince Rupert in the story. Though he played a very small role (scaled down from earlier outlines), he still managed to add a certain dramatic flair. No matter what part he played in history or in fiction, Prince Rupert was nothing short of memorable.


The War of the Three Kingdoms, also known as the English Civil War, was a bloody dispute between King Charles I, who fought for his divine right to rule, against Parliament, who fought for the rights of Parliament and religious reforms. The conflict lasted between 1642 – 1651, with King Charles II picking up the reins for his father in the final couple of years. In 1648, when Charles I was held as a prisoner of Parliament and Royalist armies disbanded, Rupert took to the seas with a stolen Parliamentary fleet and harassed English in the Mediterranean. He also skipped over to Ireland to support the Irish Royalists for a time. While Rupert sailed in the West Indies briefly in 1651 before returning to the North African coast, it was the period between May 1652 and December 1652 when he effectively turned pirate.

Prince Rupert’s journey: By Akhristovderivative work: Hchc2009 (talk) – A_large_blank_world_map_with_oceans_marked_in_blue.svg, Public Domain,

Travelling the West Indies

When Prince Rupert left the North African coast and Cape Verde on May 9, 1652, he had in his fleet a total of six ships: the Swallow, his flagship; the Defiance, commanded by his brother, Prince Maurice; the Honest Seaman, captained by a man named Craven; the John, the Sara, and a Cape Verde prize (name unknown). 

It had been Rupert’s intention to seek Barbados, but their navigation was off, and on May 29th, they landed instead in Saint Lucia. There, his fleet were able to restock their water supplies and take on ample fresh meat in the form of wild hogs and wild goats. Over the next days, they sailed northward along the Leeward Isles, and ended up in Martinique, where they received the poor news that Parliament was in possession of Barbados. Good thing he didn’t go there! 

The problem, Rupert quickly realized, was that during the time that he spent exploring the African coast, Parliament had moved to establish their presence in the West Indies and shore up control of their the colonies, especially those, like Barbados, who had Royalist leanings. Where he expected to be welcomed by fellow Royalists, he found himself in hostile waters. This made it harder for him to find safe harbour, and therefore, replenish supplies. But he wasn’t there for the beaches, so he resolved instead to be hunter instead of prey, a Prince Pirate of the Caribbean on the lookout for Commonwealth and Spanish ships. 

On the lookout for rich prospects, in the beginning of June 1652, Rupert’s fleet headed for Montserrat, an English colony known for its sugar plantations. Thanks to the sugar being in high demand, merchant ships were thick in the area. Rupert was like a shark streaming through waters teeming with fish. His strategy worked, and he managed to capture two English prizes, one loaded with a hold full of sugar. But it wasn’t without loss. During a heated exchange near Nevis, Rupert’s personal secretary was killed, as was the captain of the Defiance

A pirate prince couldn’t spend all his days ravaging the Caribbean without trying to make a few friends. Around June 8th, Rupert’s fleet arrived at St. Christopher’s (St. Kitts) where he attempted to trade with the Dutch merchants in the town, but the English settlers threatened retaliatory measures against the Dutch if they assisted Rupert, including the confiscation of their goods. In response, Rupert anchored in the French controlled harbour and traded there briefly.

Rupert’s fleet continued northward to the Virgin Islands where he finally found a bit of respite. There, he established a temporary base and spent the next several weeks outfitting his ships and fortifying the harbour against the Spanish. Food supplies were poor and everyone, including Rupert, were forced on mean rations. At the end of August, several men had enough of the conditions. The last anyone saw of them, they were sailing toward the Spanish colony of Puerto Rico on a stolen pinnace.

This put paid to Rupert’s sojourn. He had hoped to wait out hurricane season in a sheltered cove, but with the defectors heading towards his enemies, with full knowledge of where to find him, he pulled up anchor and headed for Anguilla.  

On September 13th, catastrophe struck in the form of a hurricane. This hadn’t been the first time that Rupert had encountered the power of a Caribbean hurricane. A year earlier, his fleet had been encountered a hurricane. After three days of trying to keep her afloat, his flagship, the Constant Reformation, was destroyed with the loss of all her crew (333 souls). Before she went down, Prince Maurice brought the Defiance close along the Constant Reformation to try to save his brother and as many crew members as they could, but conditions were too dangerous to launch a full-scale rescue. Rupert had resolved to stay with his crew and go down with his ship, and he would have, were it not for his men forcibly bundling him into the only boat and sending him across to the Defiance.  

Now a year later, another storm was coming down hard on them. This hurricane was an absolute beast. Rupert’s Swallow ran before the storm for four days. They could barely see one end of the ship to the other, and they lost their main sails. At the worst of the storm, the ship was being propelled toward jagged rocks, but in a last minute reprieve, the wind shifted and steered them clear of the rocks. They survived, barely. 

When the hurricane passed, Rupert realized the extent of the storm’s devastation: his fleet was lost, and most heart-rending for him, there was no sign of the Defiance. Rupert’s best friend, his brother Maurice, was lost at sea.

Prince Maurice of the Palatinate: By unbekannter Maler via Wikimedia Commons

Four days, on September 17th, the Swallow limped into St. Ann’s in the Virgin Islands, and took on fresh water and supplies, which were scarce because of the hurricane. Everyone was on reduced rations and starvation was a real threat. Over the next week, they sailed south looking for supplies. 

Rupert searched fruitlessly for word of his brother and the rest of his fleet. For years, rumours circulated of Maurice being sighted across the West Indies, from Puerto Rico to Hispaniola, but they amounted to nothing. The Defiance was never heard from again. The Honest Seaman was also lost, but there were a few survivors. Several months later, Captain Craven turned up in France. 

The loss of his fleet spurred Rupert to recoup some of his losses. In early October, he returned to Montserrat and captured a small English prize and tried to pick off a Spanish ship but couldn’t catch her. 

On October 10th, Rupert arrived in Guadeloupe where he received word that the English Commonwealth was now at war with the Dutch Federation over a trade dispute. More tantalizing, he learned that there were rich prizes in Antigua, another English colony. 

 At the end of the month, the Swallow arrived in Antigua, but instead of sailing into Five Island Harbour, he approached with uncharacteristic caution. Rupert sent an advance party of fifty men, led by Captain Holmes, to scale the hill where an embankment of guns protected the harbour. 

Holmes and his men spiked the guns then gave the signal for Rupert to sail into the harbour to capture the two English ships anchored there. The Swallow fired on one of the ships and crippled her, but the other surrendered without resistance. For the next couple of days, while the English soldiers created barricades on the beach to prevent a Royalist landing party, Rupert plundered the crippled ship then set sail with his prize.  

Rupert would stay only another month in the West Indies. On December 12,1652, the Pirate Prince of the Caribbean closed off this chapter of his life and headed back to Europe with far less than he had hoped to return with. But at least Rupert would live to see another adventure. 

This article originally appeared on the English Historical Fiction Authors Blog.


  1. Sally Johnson

    Thank you for this … I LOVE Rupert. He spent his life enabling other kings to be successful, and I don’t think he gets his due (and nor does Maurice). I was hoping Harry and Megan would name their baby Rupert — maybe next time!

    Liked by 1 person

    1. I love Rupert too, and I absolutely agree with you. I also loved how close he was to Maurice.


  2. Excellent post. While (as you know) Rupert is no favourite of mine, one must admit the man has dash and depth – and an amazing quantity of derring-do. I loved how you had him pop up in your latest book. Actually, I loved the entire book 🙂

    Liked by 1 person

    1. Thank you so much on all accounts! I had originally planned for Rupert to show up earlier but alas my characters had other plans. 🙂


  3. Wow a fascinating read, thanks. Poor old Rupert didn’t have much luck did he, between the hurricanes and the politics in the Caribbean.,

    Liked by 1 person

    1. Thank you very much! The poor man did indeed have a rough time of it those years. He did a great deal to support his cousin.

      Liked by 1 person

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