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Grand Cayman and its sister island Cayman Brac could not be more different.

While the former has a wall-to-wall stretch of hotels that can feel more like a tourist trap than a Caribbean escape, the latter is a sleepy, uncrowded, 14sqm hideaway that offers some of the most stunning vistas in the archipelago. 

But “the Brac” (Gaelic for bluff), as locals call it, was not always so tranquil. In the 17th and 18th Centuries, pirates stopped regularly on the island to take shelter from storms and to stockpile water, wood and food -- especially turtles, which they nearly wiped out.  

According to Marina Carter, author of Pirates of Cayman, the Brac was located along the Spanish galleon trade route from the New World to Europe. Each year, Spain sent ships to bring back gold from mines in Lima, Potosi and Mexico. “A successful attack on one of these treasure ships was like winning the lottery for a pirate,” Carter said. “The galleons were well-protected, but there was lots of other commercial traffic in the Caribbean which pirates could prey upon.” French and Spanish pirates sometimes attacked Cayman Brac because the British governor lived on the island and it was considered the seat of the British government. The Cayman Islands remain a British overseas territory today.

Located just 90 miles northeast from Grand Cayman (a half hour flight), the Brac now attracts divers, hikers, rock climbers and birders. English is widely spoken and US dollars are accepted as readily as Cayman dollars (though they are worth 20% less because of the exchange rate).

Unlike other Caribbean destinations where high crime rates plague tourism, Brac locals do not even lock their doors because of the island’s safety, efficiency and by-the-book religious conservatism. The less than 2,000 friendly residents actually celebrate the island’s pillaging past every fall during Pirates Week, with events like underwater treasure diving, fireworks and costume contests.

Running the length of the island, Cayman Brac’s namesake limestone bluffs have been used as a navigational landmark since Christopher Columbus’s heyday. The craggy grey rock is pocked with caves and sinkholes, and rises to a 140ft sheer cliff at its eastern end. Local lore claims that Blackbeard and other buccaneers hid their treasure in these caves, and a few of them are open to the public.

Despite its name, the Bat Cave does not always have fruit bats hanging around in it, and limestone cracks allow sunshine and various vines, underbrush and trees to flourish inside. Rebecca’s Cave is named after an 18-month-old girl who died inside it during a hurricane in 1932. People still leave flowers at her gravesite.

The Great Cave is the hardest to access, but its multi-hued stalagmites and stalactites make it the most striking. Peter’s Cave overlooks Spot Bay and the south side bluffs and can be reached by trails from above or below. The hauntingly desolate Lighthouse Footpath, home to flocks of brown boobies, is an eerie mix of palm trees, spiky scrubs with bright flower buds and jagged lunar-looking boulders. Customized guided nature and cultural tours can be arranged for free by emailing the Cayman Islands Department of Tourism.

When prodded, guides may tell the island’s most infamous tale of pirates’ booty, discovered in an area called Slaughterhouse on the southeastern coast of the island. Local historian and fisherman, 73-year-old Tennyson Scott said that when he was 14, he set out to find buried fortune with a friend. “We were kids,” he recalled. “You want to believe you could find treasure.” They came across a boulder with a skull etched into it and found an easy place to dig. After getting knee-deep, Scott hit something hard -- what he assumed was the island’s limestone foundation. A few years later, someone came by with a metal detector and the machine went off at the same spot. Scott had struck a large flat stone placed on top of a buried chest. The treasure trove was filled with coins, silver and paper money -- at least, that is how the story goes. The chest was never turned into authorities and was reportedly traded for cash. Other plunder found on the island, according to Carter, include Spanish silver coins and a clock made in Barcelona in 1729.

Once you grow weary of treasure hunting, hit the sandy beaches along the Brac’s southwest coast, where most of the hotels and vacation rentals are clustered. They will most likely be blissfully deserted. Locals joke that when a family sees another group picnicking on southside’s Public Beach, they leave for a less-populated stretch of sand.

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