Sailing the Florida Keys

Troop 116 charters a pair of bareboats to spend a week sailing the Florida Keys

Sailing a chartered bareboat though Biscyane BaySailing a chartered bareboat though Biscyane Bay

Somewhere on the far side of midnight, I awoke to the unexpected sensation of flying horizontally through the air. This was followed by the sensation of coming to an abrupt stop as I smacked into the cramped cabin's far wall, which had somehow managed to become the floor while I was sleeping.

The fair ship This Life let out a groan, the bilge water below gurgled alarmingly, and it slowly dawned on me that the tide must have finished going out. That would explain why our sailboat had suddenly keeled over at a 30-degree angle, leaving us high and dry on the Biscayne mudflats.

I shook the cobwebs from my head, vaguely wondering why I wasn't in much pain, seeing as how I had fallen out of my berth and slammed into the lumpy pile of junk that had accumulated against the cabin wall. That’s when the lumpy pile said, "Ow. That really hurt. You wanna get off me now?"

Stranded in Stiltsville

I don’t care what anyone else says, I maintain we merely committed an act of unintentional anchorage.

Sure, I was the one had who insisted we end our week of sailing the Florida Keys by racing the setting sun far enough north that we could cut over to Biscayne Bay through Stiltsville, a collection of decaying wooden houses built on pilings out in the middle of the water a mile south of Key Biscayne.

How was I to know we'd waste an hour hanging around off Key Largo waiting for the other boat our troop had chartered to extricate itself from a reef? (They eventually radioed us to go on ahead as they were going to have to wait for a tow.) How was I to know that the navigable channels through Stiltsville were so twisting, so poorly marked, and, as it turned out, so incredibly shallow?

More importantly, how did such a clearly inept group of Boy Scouts with only one actual sailor among them—a former scoutmaster and avid boater we'd coaxed out of retirement for the trip—manage to get their hands on such a fine pair of sailboats for a week?

All it took was about $2,000 per boat and a call to Captain Mike.

Chartering a Bareboat

The boys of Troop 116 learn (the hard way) that sea shanties are actually work songs designed to help keep cadence during group tasks like weighing anchor.
The boys of Troop 116 learn (the hard way) that sea shanties are actually work songs designed to help keep cadence during group tasks like weighing anchor.

Mike McKenney's parents gave up the 9 to 5 grind long ago to live aboard sailboats and later start Miami Beach's Go Native Yacht Charters (800-359-9808;

Before he let us take his boats, Capt. Mike treated us to an interminable and informative consultation session—recommending routes, stops, and anchorages—loaned us a sheaf of charts and tidal tables, and took us out for a test run.

Our primary objective that first day to get all the simplest things wrong at least once so that, by the time tomorrow rolled around, we would look like experts in front of the boys.

Capt. Mike's primary objective, as he gently corrected our mistakes, was to make sure his company wasn't chartering its boats to thorough incompetents.

Luckily, we proved only moderately incompetent, getting the battens caught on the wrong side of the stays as we hoisted the mainsail, attempting to haul out the jib by a sheet looped around the ropes holding a dingy to the prow, and otherwise getting hopelessly tangled up in sailing jargon.

Next day, we loaded up the boats with eight scouts and five heaping shopping carts worth of groceries. We sailed out of the harbor, turned south down the Intracoastal Waterway, entered the waters of Biscayne National Park, and began practicing our tacking, our jibing, and, once the boys realized they could do this, our stomach-lurching 180s.

At Sea

No, the photo isn't crooked--check out the horizon--but when you bury the rail at 18 knots like 13-year-old pilot Quinn Manwarring here, you tend to tilt thrillingly to one side.No, the photo isn't crooked—check out the horizon—but when you bury the rail at 18 knots like 13-year-old pilot Quinn Manwarring here, you tend to tilt thrillingly to one side.

The week was relaxing. We spent as much time at anchor as we did racing the other boat and trying to bury the rail at 18 knots. We'd stop for lunch and to snorkel the coral reefs, hang out on buoys under which silvery schools of ferocious-looking barracuda huddled, and swim back and forth between the boats to trade Jimmy Buffet CDs.

At night, we'd marvel at the starfield above and feel pity for the landlubbers on Key Largo way off to starboard, confined to their narrow roads lined by the sickly yellow glow of artificial lights. We only made it as far as Islamorada —not even halfway to Key West—before it was time to turn around. So we motored over to land for the first time in days and had a landlubbing evening of much-needed showers, roadhouse burgers, and a night spent tied to a public dock rather than bobbing in the current.

Next morning, we caught the Gulf Stream to zip back north, and turned back toward Biscayne Bay, at which point the crews of both boats used their week's-worth of collective sailing skills to commit, a few dozen miles apart, those acts of unintentional anchorage.

Sunrise over Stiltsville, with Key Biscayne on the horizon.Sunrise over Stiltsville, with Key Biscayne on the horizon.

Our ineptitude did grant us one unforgettable moment. After my tumble out of bed, I found a way to wedge myself into the tilted forward berth. I'd finally managed to drift off when, just before dawn, the boat let out another groan and suddenly righted itself, throwing us all to the floor again.

I staggered up onto the deck to wait for the incoming tide to put enough water under us so we could push back into the channel. As I watched, the slowly lightening horizon suddenly caught on fire, threw a glorious pink and orange sunrise across the sky above the rickety houses Stiltsville, and lit up the waters of the wide Atlantic beyond.

Tours Under $995 G Adventures

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This article was by Reid Bramblett and last updated in June 2012.
All information was accurate at the time.

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Copyright © 1998–2013 by Reid Bramblett. Author: Reid Bramblett.