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Pine Island Sound Pirates

At World's End, where the law is scarce and the water is vast, pirates have always found their home. Florida from the 1600's into the start of the 19th century was just such a place, and the pristine waters of Southwest Florida's Gulf Coast were ideal pirate safe havens. Even when the Spanish and British Navies were chasing pirates out of the Caribbean, wise pirates like Black Caesar and Brewster Baker made their way up the Florida coast. While Tampa Bay is typically associated with the most famous Florida pirate--Gasparilla, in truth his legend is based 100 miles to the south in Charlotte Harbor. It was there and the waters of Pine Island Sound where most documented pirate history. If you're going to Do Florida Right, at some point, you'll have to commandeer a ship, hoist the colors, a set a course for the ghosts of pirates' past. 

Our pirate adventure took us to Bokeelia (originally Bojeelia) to Four Winds Marina, a stone's throw from where a lesser known pirate, Brewster 'Brew' Baker, led a community of pirates in the early 1800's. The fine folks at Four Winds Marina set us up with 4 pirate vessels (very nice new rental boats), and off we went. Our first stop took us 10 miles south to Redfish Pass. Redfish Pass is an infant in geologic time, only having been in existence for fewer than 100 years. It was opened by the Hurricane of 1921, splitting Captiva into two islands. More than 200 years ago, however, when there was only 1 Captiva, the island was used by two different pirates that called themselves Black Caesar and allegedly by Gasparilla as well. 

The next stop took us up to Captive Pass on south end of Cayo Costa. which is about as close as one can get to an unspoiled Florida barrier island. Cayo Costa looks very much the same today as it did when the likes of Brew Baker and Gasparilla were sailing around it 200 years ago, which can't be said for any other island for 70 miles in any direction. The state park at Cayo Costa has kept it from being developed while nearly all the surrounding islands, including some in the sound like Useppa and Cabbage Key, have been overtaken by the footprint of man. 

It's hard to complain about Cabbage Key, however. In fact, that was our next stop. We had to see what Jimmy Buffett had been singing about all these years. The Cabbage Key Inn and Restaurant was the inspiration for Jimmy Buffett's famous song. While the burger was good, it's clear that Jimmy was more taken aback by the island, not the burger. Cabbage Key is a beautiful small island with a 38ft Calusa Indian shell mound at the center. The staff at the restaurant was a bit surprised to see 30 pirates walk through the front door, but were accommodating nonetheless and found us all seats and good food. 

It was hard to leave paradise, but knowing that yet another idyllic location and more Florida history awaited, the crews were gathered and sails hoisted and off we went for the famous Boca Grande Pass. Today, Boca Grande Pass draws far more fame as the best tarpon fishery in the world, and had tarpon been edible and not so exhausting and time consuming to catch that may have been the case 200 years ago, but then it was all about one thing: deep water. Pirate ships need deep water, and Boca Grande is one of the deepest natural channels anywhere in Florida. What was best for pirates like Brew Baker was that the deep water quickly jumped to shallow water, and only those with a strong sense of the area could navigate it without running aground, which unfortunately is still true today even with fancy maps, channel markers, and GPS. Naval ships chasing pirate ships wouldn't enter the pass for fear of running aground which made the harbor a safe haven for pirates for hundreds of years. Florida's phosphate industry also took advantage of these deep water channels, and built railroad docks out into the middle of the pass where large barges could load up phosphate without worry of running aground. The skeleton of these docks are still there today. 

The day ended back where it began, at Four Winds Marina--but this time on the inside at the Lazy Flamingo. The remaining pirate crew, exhausted from a full day of plundering, recharged with some food while the captains finally treated themselves to a pint or two. It ain't easy being a pirate. Wait, yes it is. It's extremely easy. Let DoFloridaRight prove it to you--call (856) 220-1931 or email This email address is being protected from spambots. You need JavaScript enabled to view it. today. 

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