Shiver me timbers! 3 Swashbuckling pirate vacations

Do you often find yourself staring from the office window and fantasizing about adventures on the high seas?

And are you prone to affectionately referring to friends and colleagues as ‘me hearties’? Finally, are you fond of parrots (even if you don’t presently have one perched on your shoulder)?

If you’ve answered ‘aargh’ to all these questions, there’s a good chance you’re of a piratical persuasion.

And the good news is that there are still many vibrant global vacation destinations where you can walk in the footsteps of real buccaneers and steep yourself in pirate history.

To prep for your sojourn as a salty seadog, bring plenty pieces of eight, and pack a plastic cutlass, a tricorn hat and a couple of bottles of Caribbean Appleton or Cockspur rum.

Then be sure to book airport parking at to leave your trusty vehicle safely stowed until you return — they’ve got spaces everywhere from Seattle to the Spanish Main.

Now that you’re ship-shape, let’s set sail for three swashbuckling pirate vacations.

1. Port Royal, Jamaica

Port Royal is situated on the same Palisadoes tombolo as Kingston’s Norman Manley International Airport, so it’s a short hop from your airplane.

Once dubbed ‘the wickedest city on earth’, Captain Henry Morgan ruled the pirate roost here and was buried in the local cemetery until the site was washed out to sea in a massive 1692 earthquake.

With an old gaol, naval hospital, parade ground and a 17th Century fort, this destination deserves its place on your travel treasure map.

And you can also hire a boat at Morgan’s Harbor Marina to take you to Lime Cay — an uninhabited islet that’s perfect for a private pirate party.

Port Royal, Jamaica

2. Tortuga, Haiti

Tortuga is now part of Haiti, but in its pirate heyday in the mid-17th Century, it belonged to the province of Hispaniola.

And French pirates like Francois L’Ollonais used this 40km long island as a stronghold from which to raid nearby Spanish colonies.

Reserve Tortuga accommodation on Airbnb and sunbathe and snorkel on the breath-taking Pointe-Ouest beach, named by Conde Nast Traveler as one of the world’s most beautiful.

But first, you’ll have to charter a boat from Port-de-Paix on Haiti’s mainland to get there — if you’re dedicated to the pirate cause, it shouldn’t be too tricky to plot a course.

3. Aberdeen, Scotland

This civilized city in Scotland’s north east isn’t traditionally associated with piracy, but researchers from the University of Aberdeen have recently discovered that in the 15th and 16th Centuries, locals were up to their necks in stolen booty.

On one occasion in 1530, Scotland’s King James V intervened when owners of the Jhesus of Gdansk, a Polish merchant ship which wrecked off Cove, accused locals of plundering the cargo.

Modern Aberdeen is home to lively nightlife, great golf courses and an excellent soccer team — well worth a visit.

After visiting these pirate capitals, you’ll be swinging from the main sail and singing sea shanties — so take time to calm down and find your land legs before returning to normal life.

That’s our list! Add your favorite pirate destinations in the comments section.

Olivia Watson

Olivia is a world traveler who has been to 27 countries in just over 15 years. She loves to share her knowledge of traveling to help others travel safer, cheaper and have more fun.
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