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El Morro, Old San Juan, Puerto Rico. Photo by Jeff Gunn on Flickr.

El Morro, Old San Juan, Puerto Rico. Photo by Jeff Gunn on Flickr.

Sure, the Caribbean pirates of yore were a cutthroat crew: They plundered, pillaged, and sent many a scurvy dog to Davy Jones’ Locker — then squandered their booty on rum and loose women.

But nearly two centuries after their last victims walked the proverbial plank, those swashbuckling scoundrels still command rock-star power.

Maybe it’s the devil-may-care attitudes flaunted by fictional pirates like Treasure Island’s Long John Silver, Peter Pan’s Captain Hook and Pirates of the Caribbean’s Jack Sparrow — hoisting their Jolly Rogers on the mainmast, unfurling their cryptic treasure maps, sporting their earrings and puffy shirts in an otherwise overstarched age.

Maybe it’s the colorful monikers of real-life pirate captains — Blackbeard, Calico Jack Rackham, Black Sam Bellamy — whose crimes reflected little of the Hollywood image.

Whatever the reason, if you’re hooked on the pirates of the Caribbean, we’re here to help you hang with them. Not literally, of course, unless you get a bit carried away with the rum and cutlasses.

No, we’re going to guide you through what were once some of the most pirate-plagued islands on the old Spanish Main. So ahoy, mateys! Pack up some pieces of eight and repeat with us: “Arrgh, me hearties — ’tis a pirate’s life for me.”

Today’s Pirate Tour: Puerto Rico

For hundreds of years, Puerto Rico was a stronghold of Spain’s colonial empire in the Americas, protecting treasure-laden galleons from the onslaughts of pirates and privateers. It’s now one of the Caribbean’s top cruise ship destinations. Before casting off, take the time to tour a pirate lair or two.

Arrgh -- 'tis a pirate's life for me, at least on vacation.

Arrgh — ’tis a pirate’s life for me, at least on vacation.

The beautifully restored colonial-era town of San Juan is just a short walk from the cruise ship docks, with hordes of passengers descending on it every week.

Back in 1595, San Juan was subject to another kind of assault, when English privateers Sir Francis Drake and John Hawkins tried to capture a fortune in gold and silver there. But even Drake’s fleet of 23 ships couldn’t take massive Fort San Felipe del Morro (El Morro for short), built atop a promontory overlooking the harbor. With its cannons, tunnels and towering walls, El Morro is now a World Heritage Site.

Legendary local pirate Roberto Cofresí was executed here in 1825. Before embarking on his pirate career, Cofresí grew up in the southwestern Puerto Rican port of Cabo Rojo, now sometimes dubbed El Pueblo de Cofresí.

Rincon Beach, Puerto Rico. Photo by Bulaclac Paruparu on flickr.

Rincon Beach, Puerto Rico. Photo by Bulaclac Paruparu on flickr.

Celebrated for splitting his loot with the poor, Cofresí may or may not have been the high-seas Robin Hood his admirers contend. But Cabo Rojo’s attractions are not in doubt: scenic beaches and cliffs, friendly little hotels, and atmospheric seaside restaurants. Try Cofresí’s favorite fish: barracuda for two.

Cofresí is rumored to have buried some booty in the cliff-side caverns around Rincón, a beach town on the northwestern shores of the island. English and French pirates also gathered here.

To nurture your own inner pirate, and perhaps seek some buried treasure yourself, drop anchor at the Villa Cofresí Hotel and Restaurant on Rincón Beach, where you can try a “Pirate Special” cocktail, served in a coconut.

If that doesn’t shiver yer timbers, you can also swim, surf, kayak, snorkel, fish and watch for whales.

Next Up: Jamaica

 

An earlier version of this piece appeared in EnCompass Magazine.

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According to government and private surveys:

  • Leading-edge baby boomers (born between 1946 and 1955) and seniors account for four out of every five dollars spent on luxury travel today.
  • Roughly half the consumer spending money in the U.S.--more than $2 trillion--is in the hands of leading-edge baby boomers and seniors.
  • Baby boomers (born 1946-1964) travel more than any other age group.
  • When asked what they would most like to spend their money on, baby boomers answered “travel” more than any other category, including improving their health or finances.

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