The Ultimate Pirate Road Trip: 5 Ports to Gold and Glory
Batten the hatches, hoist the mainsail, and swab the poop deck! We’re about to embark on an adventure that will have you crossing cutlasses with Florida’s fiercest pirates and finding treasure in unexpected places.
Yup, you guessed it – we’re going on a pirate road trip!
So, I suppose it’s more like fill the gas tank, grab some snacks, and turn to your favorite radio station…
But don’t worry. While our mode of transport may be the 21st century, the rest of the adventure is strictly a dive into the swashbuckling past.
Pirates in Florida??
Before we head out, you might be wondering if there were actually pirates in Florida. After all, isn’t that sort of a Caribbean thing?
The answer is YES! There were pirates in Florida, including the infamous Blackbeard and the “Sea Dragon” himself, Sir Francis Drake! The Gulf Coast was a popular place for pirates to hide, as there were plenty of inlets, bays, and marshes where they could disappear from warships.1 There were also constant disputes among the countries vying for control of the region (Spain, England, and France), and employing pirates was a good way to get back at one another.
However, while we know pirates were in Florida, much of what we know about them is so tightly interwoven with legend, it’s nearly impossible to untangle the pure history. Perhaps this is unsurprising, as sailors’ knots are known for their resistance to being unraveled.
Nevertheless, there are a few things we know to be myths:
One is pirate talk. Without a written record of their vernacular, we don’t actually know if they said “arrgh” after every sentence. Treasure maps are also fictitious – pirates generally stole useful items rather than money, and what money they had was usually spent on liquor before you could bury it. And as for walking the plank…pirates were more efficient than that: they’d just throw you overboard, outright.2
Even stripped of myths, the pirate life is still rip-roaring and raucous – the perfect makings for our most entertaining Florida road trip yet!
The Ultimate Pirate Road Trip
On our pirate road trip, we’ll meet up with Florida’s most famous pirates. We’ll go from cityscape to long stretches of sand, and discover that the treasure lies in taking the journey…
Port #1: St. Augustine
Robert Searles and Sir Francis Drake
Our first pirate road trip stop (or “port,” in keeping with the whole sailing thing) is the illustrious St. Augustine. Known as The Nation’s Oldest City, this locale was also a hotbed for pirate activity.
And when we say “hot,” we mean the city got burned down by pirates – namely, by Sir Francis Drake.
At the time, St. Augustine was a Spanish city, and Spain was in a vicious rivalry with England. In the summer of 1585, it was England’s turn to retaliate, and Queen Elizabeth I had sent Drake out to “revenge the wrongs offered her.”3 So, by 1586, he had sailed across the sea and avenged his queen by turning St. Augustine to ashes. (Harsh!!)
St. Augustine was slowly but surely rebuilt…only to face off against another pirate: the dreaded Robert Searles. It was the dead of night, in summer of 1668, when Searles launched a raid, guns a-blazing.4
Silver? Stolen.
Daughters? Kidnapped.
City? Sacked.
It was a pretty bad deal. And St. Augustine had had enough – construction on the epic Castillo de San Marcos fortress began after this raid, and nothing has even gotten past those walls.
Today, you can still tour this astounding 300-year-old coquina structure and take in the wonderful ocean views from the top. It’s also fun to explore the cafes and shops along the historic city streets. Best of all, you can experience a slice of pirate life at The Pirate Museum! (Tours come complete with a scavenger hunt – I got a “jewel” as my booty!)
St. Augustine can be a few hours stop, or easily an entire day on your pirate road trip!
Port #2: Boca Raton
Edward Teach AKA Blackbeard
A surprisingly quiet visitor to Florida’s shores was the blood-thirsty Blackbeard! Known for blockading Charles Town, carrying three pistols slung across his back, and sticking lit matches into his hat to make himself look scary, it might be surprising to learn someone like him also appreciated some quality R&R.5
But rather than burning down or blockading Boca Raton, he simply harbored there between raids. It was a place of refuge, rest, and freshwater for the weary pirate. (And, legendarily, a place to bury his treasure.)6
Today, Boca Raton is still a relaxing getaway where you can soak up the sun, enjoy fine dining, and browse through upscale shops and family-owned boutiques. It’s a great place to rest – in style! – after a long day at sea.
Port #3: Biscayne National Park
Black Caesar
A legendary pirate (so legendary, in fact, some historians are unsure of his existence7), Black Caesar embarked on a life of piracy to attain the greatest treasure of all: freedom. Said to have been incredibly tall and cunning, Black Caesar and his friend escaped a slave ship during a storm that sank the vessel.
Together they created a foolproof con: pose as helpless, shipwrecked men and lure in ships from the reef – then attack and steal their goods!!8 These unconventional pirates were quite successful with this technique, and legend states they buried their bounty on Elliott Key.
While we can’t promise you’ll find any gold or jewels, you can take an incredible hike around Elliott Key! It’s the largest island within Biscayne National Park (a park that’s 95% water!) and includes campgrounds and roughly 13 miles of different trails.9
The 1.1 mile Elliott Key Trail is most popular for day-trippers, but with longer trails to explore and a place to sleep, you can make the Key a longer stay on your pirate road trip if you so desire!
While you’re in the area, we also recommend checking out Black Caesar’s Rock! This little island is also part of Biscayne National Park, along with the inlet called Caesar Creek. It was here that Black Caesar was said to have kept his harem of over 100 women, as well as a prison camp of his captives he hoped to ransom.10
There are so many stories about Black Caesar, and if there’s a grain of truth to any of them, he may have been the scariest scallywag of them all! Ironically, retracing his steps in the Florida Keys is a beautiful and peaceful endeavor.
Port #4: Sebastian Inlet State Park
Henry Jennings
Henry Jennings might not be the best-known pirate, but he lived out every pirate’s dream – to actually accumulate a bunch of wealth and retire with it. (The life expectancy of a pirate – a “career” generally sought by young men – was 26 years.)11
In 1715, a Spanish treasure fleet set sail from Cuba, ordered to come home to Spain (who was in desperate need of money). Unfortunately, it was hurricane season, and the ship was caught in a storm and sank – with all of the treasure – around Sebastian Inlet.
Jennings heard about the disaster and set out from Jamaica to profit from Spain’s misfortune. He found the Spanish already there, trying to salvage what treasure they could. Jennings attacked their camp and raided their storehouse, stealing over 340,000 pieces of eight. But, on the bright side, he didn’t kill anyone! What a nice pirate!12
Today, you can enjoy everything the stunning Sebastian Inlet State Park has to offer – including the McLarty Treasure Museum!!
This stop on your pirate road trip will mingle the beautiful great outdoors and sandy beaches with the amazing history of Spain’s lost treasure fleet. It’s the combo you never knew you needed!
Port #5: Tampa Bay
José Gasparilla
A pirate road trip wouldn’t be complete without some mention of the Tampa Bay Buccaneers. (“Buccaneer” refers to pirates who operated in the Caribbean!)
The most notorious Tampa Bay Buccaneer isn’t a quarterback or wide receiver – it’s legendary pirate José Gaspar – better known as José Gasparilla!
Now, like Black Caesar, there are doubts as to this pirate’s existence, but whether or not he really plundered ships around Florida, he is certainly a presence here now!13
Every year, “Ye Mystic Krewe of Gasparilla” (a club, of sorts) dresses up, brings a fully-rigged pirate ship into the harbor, and demands the mayor hand over the keys of the city. Thus begins the Gasparilla Pirate Fest!
We recommend planning your pirate road trip so you’ll be in Tampa Bay on January 29th – then you can watch invasion, the pirate parade, and jam out to the pirate concert as the sun sets. It’s an all-day celebration of sailing the seven seas!
If you have kiddos, you can head to Tampa early – on January 22nd – for the Children’s Gasparilla festivities!
Bonus Port: Orlando
Captain Hook, Captain Jack Sparrow, and Sebastian the Black
What sort of pirate road trip plan would be complete without at least a mention of our favorite Disney pirates?
They might be fictional, but if you want to include Captain Hook and Captain Jack Sparrow in your trip, then we’d recommend a day (or several) at Disney World! Soar through the sky and watch the sword fight between Peter Pan and Captain Hook on Peter Pan’s Flight, then join Captain Jack Sparrow’s crew on the Pirates of the Caribbean ride!
And if you want a true taste of the pirate life, we recommend an evening out at the Pirates Dinner Adventure! Enjoy a hearty meal and swashbuckling show as you witness the tale of nefarious Sebastian the Black!
With great food, beautiful locales, and enthralling history, a pirate road trip is the BEST kind of road trip!
Have you been to any of our pirate road trip ports?
Who’s your favorite pirate (fictional or real)??
Let us know in the comments below, and we’ll see you on the next adventure!
Cover Image
Photo: Unsplash
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