Pirates and Plundered Treasure: A Tour of Key West’s Old Town

In the sun-scorched heart of Key West, pirates didn‘t just seek treasure, they demanded it.

On this stroll through Key West‘s historic Old Town, you‘ll retrace the steps of famous pirates, treasure hunters and ‘wreckers‘, as the sailors who braved the merciless sea in search of wrecked cargo are known. If you dare to venture to the places where legends were forged in cutlass and flame – from the Cuban hangouts of famous pirates like Blackbeard, to gravestones in saloons, and the haunted homes of ship captains – you‘ll get the chance to sip rum and reawaken the history buried beneath the soil.

Starting in Mallory Square, you‘ll be guided by Captain William Shade, the eccentric and unconventional ghost of an 1800s pirate ship. From there, you‘ll make your way to the Key West Historic Memorial Sculpture Garden where I’ll tell you how Captain David Porter transformed the sleepy fishing village into a thriving naval station. You‘ll then venture down Duval St, hearing about the ghouls that linger in the now lively street‘s shadows, as you make your way to the oldest residence in southern Florida, the Oldest House Museum & Gardens Key West. You‘ll also see Captain George Carey‘s House which was transformed in the 1900s into a local hub that hosted Gloria Swanson, Tennessee Williams, and Ernest and Pauline Hemingway. By the time our tour ends in front of the Key West Shipwreck Museum, you‘ll have met the legendary characters that left their mark on this island city.

On this tour, you‘ll get a chance to:

• Duck into El Meson de Pepe‘s Restaurant and Bar for a riotous throwback to the days when the only law was the pirate code and every night was a treasure hunt, where the rum flows freely and the salsa never stops
• Stumble into the infamous Capt Tony‘s Saloon, where the spirits aren‘t only in the bottles, and the property‘s grim history includes a hanging tree and several tales of the departed
• See the Oldest House, also known as the den of the wreckers, now a museum and time-travelers ticket to an age when ‘finders keepers‘ could mean anything from a barrel of rum to a ship full of gold
• Discover Audubon House and Tropical Gardens, a gateway to Key West‘s wild, untamed past
• Dive headfirst into Mel Fisher‘s Maritime Museum, the holy grail for armchair buccaneers and would-be treasure hunters where you‘ll hear about history‘s most daring underwater heists that seem to prove the old adage, “fortune favors the bold”
• Stand before the old Custom House, where straight-laced customs agents once tried to tame the wild tides of Key West

This isn‘t your grandmother‘s stroll down memory lane. Steel yourself, my friends. By following Captain William Shade‘s ghost through Key West, you‘re not just retracing history, you‘re awakening it.