Skip to main content

Everglades Challenge: An Insane Small-Boat Race Down Florida

The gun sounds at 0700 and immediately dozens of crews, both single- and doublehanded, begin dragging their boats across the beach into the water. Welcome to the start of the annual Everglades Challenge, the only event I’ve sailed where the SI’s contain the following warning: If you are not an expert paddler and/or sailor, do not enter this race. Even if you are a well-prepared expert you may DIE—yes, you may DIE…
  • Author:
  • Updated:

The gun sounds at 0700 and immediately dozens of crews, both single- and doublehanded, begin dragging their boats across the beach into the water. Welcome to the start of the annual Everglades Challenge, the only event I’ve sailed where the SI’s contain the following warning: If you are not an expert paddler and/or sailor, do not enter this race. Even if you are a well-prepared expert you may DIE—yes, you may DIE…

Dragging your own boat into the water is only one of the primary qualifications for anyone wishing to take part in the adventure that lies ahead—a 300-mile rowing, sailing or paddling marathon down Florida’s Gulf coast.

Your boat must also have a mast that can be easily lowered for going under bridges, minimum draft for negotiating extremely shallow water, and be capable of being rowed, paddled, poled or sailed. Because certain parts of the various routes contestants may follow are exposed to the open Gulf of Mexico, you need a reasonably seaworthy craft that can be reefed down in a blow. Finally, because few entrants finish the course in under four days, you should be able to sleep on your boat and drag it up on the beach for camping.

A Race Like No Other

Every year on the first Saturday in March, an eclectic collection of small boats gathers on the beach at Fort Desoto Park just south of St. Petersburg on Tampa Bay, bound for Key Largo, some 300 miles away around the southern tip of Florida. Steve Issacs is the “chief” of the Watertribe, the organization that sponsors the race, and everyone who enters the EC, as it’s called, must join the tribe and take a tribal name. Mine is “Sawhorse.” Many tribe members band together during the race, even though that means limiting their speed to that of the slowest boat in the group.

The main goal of everyone entering the EC is simply to finish. Anyone who completes the course in eight days or less is entered into a hall of fame, and given a shark tooth necklace and ceremonial paddle. Historically, only half of the fleet finishes each race. In 2012—a bad weather year—only 17 of the 84 starters made it to Key Largo within the eight-day limit. In 2014 the weather was ideal, but there were still only 80 finishers out of 140-plus starters.

By any measure, the EC is a serious challenge, both mentally and physically, making it difficult for the average person to get properly prepared. For experienced sailors, even tough sailing events offer only a portion of the real preparation needed to face this race. It is different from any other boat race.

Perhaps this is also one of its attractions, especially among world-class sailors. In 2014 multihull legend Randy Smyth, Rolex Sailor of the Year Jeff Linton, Naval Academy sailing team head coach Jahn Tahanski, Hall Spars founder Phil Garland and North Sails’s Dan Neri all competed in the race. I suspect in years to come many more will take on Watertribe’s challenge.

The start this year was the biggest ever, with more than 140 boats divided into six classes, each comprised of doublehanded or singlehanded entries.

Class 1 is for paddlers and often attracts world-class contestants in single and double expedition-style kayaks and canoes. Class 2 is similar, but allows for the use of small downwind sails. With light winds this year, seven of the top 20 finishers overall came from Classes 1 and 2.

Class 3 is for sailing canoes with leeboards and stabilizing floats. The mast, beam and floats must be capable of being dismantled and secured either in or on the canoe to facilitate efficient paddling. I finished first in this class aboard my 17ft 8in outrigger canoe Voyager and was 17th overall. I was also the fifth singlehander to finish overall.

Class 4 is the largest class, with 22 entrants, and is for any monohull sailboat that can be launched off a beach. Typical entries are popular one-design sailboats, such as the Flying Scot and Lightning. Jeff Linton and Jahn Tahanski came in first in this class in a heavily modified Flying Scot with hiking racks, a bowsprit and a rig carrying 1,200 square feet of sail.

Class 5, which is for multihulls, had 14 entries this year. Three were purpose-built for the race. The rest were modified one-designs, such as Tornados and Hobie 18s. Leading the development effort was Randy Smyth in his 22-foot trimaran, Sizzors, which he has been working on for the past five years. This year he got it just right, and with perfect weather set a new course record for a singlehander, crossing the finish line in just one day 6 hours.

The only one-design class in the race is sponsored by Hobie Cat and includes three types of their ama-supported designs in both double- and singlehanded versions. The lighter winds favored the two Hobie Cat doubles this year, as they made good use of their auxiliary pedal power to finish in the top 20.

Smooth Sailing

This was Voyager’s first race and I was pleasantly surprised to see, right from the outset, that she is one fast sailing canoe. There are three checkpoints in the EC where everyone must stop, get out of their boats and sign in. The first is at Cape Haze Marina, just north of Gasparilla Island on the Intracoastal Waterway. With a following northwest wind on the first day, the fleet moved south quickly and most made the 60 miles before midnight.

This was the most exciting part of the race, with the fleet all bunched up and everyone’s adrenaline pumping. However, I knew from past experience that this hotdog all-out effort would diminish over the next 24 hours, as sleep deprivation began taking its toll. Early on there were boats everywhere, but by evening the fleet began to stretch out. I checked in at a respectable time, 1820, and proceeded on to Boca Grande, where I found a nice beach and shut down for the night. I watched as many boats passed by, knowing most would sail all night and leave me well behind.

The next day I got underway at 0500 and had a fast ride in favorable winds in the gulf around Sanibel Island down to Marco Island. I saw not a single competitor and assumed I was hopelessly behind, but I had a great sail until the wind died around 2300. By this time I was getting tired, so I threw out the hook to anchor about five miles from Cape Romano and shut down in the open gulf for the night.

I awoke in the morning to the voices of a doublehanded crew sailing a Hobie 18 catamaran, which renewed my hope that I wasn’t totally out of it. Better still, as the day progressed I began to reel in some of the boats that had passed me earlier. That afternoon, I cleared the second checkpoint at Chokoloskee—a challenging landfall in the heart of the Everglades’ 10,000 Islands. After that it was on to Cape Sable with another favorable wind that allowed me to reel in several more boats before I threw out the hook in three feet of water off Everglades National Park. The next morning I passed the beaches off Cape Sable in light air that eventually got me to East Cape. This is the lowest point in Florida before one turns east into Florida Bay to reach Checkpoint 3, which is in Flamingo.

This last leg of the race, across Florida Bay, is the one most feared by all contestants. The water is very shallow, and while the rhumb line from Flamingo to the finish at Key Largo runs only 34 miles, sailors may cover twice this distance coping with wind, adverse tides and numerous obstacles.

The smart sailors go around the west side of the bay and hook into the Intracoastal Waterway, but that adds at least 20 extra miles, which is where the paddlers made out this year—they went the short route, dead to weather in the 10-20 mph southeast winds. This is also where Voyager did well, as her 54-inch-long leeboard and long skinny floats allowed me to sail well to weather in as little as a foot of water, making me one of the few sailors to attempt the short route, which moved me up dramatically in the overall standings.

While many of my competitors were seriously sleep-deprived by days three and four, I was well rested and able to keep Voyager sailing to the max right up until the finish. Before committing to the race, I had set some guidelines for myself to accommodate my age and associated needs. First among these was getting a minimum of five hours of good sleep per day. I also wanted my minimum hoped-for passage of four days to be as comfortable and pleasant as possible.

I probably got more sleep than anyone else, shutting down every evening for seven to nine hours. Every night I cooked a good supper before retiring to what I call my “magic chair,” which can be reclined as quickly as an easy chair on shore. Voyager also carries a modified bivy that can be entered from a slot in the back, as well as a tent if I get weathered in.

Even after spending over 100 hours in my magic chair, I had no aches or pains. This was due to many years of trial and error I’ve spent developing features such as an adjustable backrest and gimbaled seat that can pivot up to 8 degrees, so I can sit level when heeled. Add to this some New Zealand long-haired sheep’s wool upholstery, and I was well supported.

At the finish, after four days and seven hours underway, I was a happy camper. I could have done better, but it would have detracted from a wonderful passage, something I am coming to treasure as much as the racing itself. In fact, I couldn’t have had a better time cruising the west coast of Florida through some of the most exotic scenery that state has to offer. I’m already looking forward to the next challenge in 2015!

Meade Gougeon is co-founder of Gougeon Brothers Inc., the maker of West System epoxy. For more on the Everglades Challenge, visit

Photos by Dana Clark; Courtesy of Gougeon Brothers; Map by AMR



Boat Review: Dufour 470

Annapolis may be the sailing capital of America, but if you looked around the United States Sailboat Show last fall, you would have no choice but to conclude most sailboats are now built in Europe. The Dufour 470 is a good example of a modern French performance cruiser. DESIGN & more


Close Encounters: Captain Sarah Schelbert

I met Captain Sarah Schelbert back in 2019 while on the boat trip from hell aboard a seaworthy but poorly run Triton 28 in the western Caribbean. I was trying to help the owner sail his boat back to Florida from the Rio Dulce, in Guatemala. Outbound from the river basin, we had more


Raising Their Voices

Many of us who are cruising sailors have been sailing mid-ocean or walking along a perfect beach in the middle of seemingly nowhere, only to be appalled at the amount of plastic trash we find. Few of us, however, have taken that disheartening reality and turned it into a more


IC37 North American Championship

This past weekend saw 20 IC37s off Newport, Rhode Island engage in fast and furious one-design racing with the win going to Peter McClennen’s Gamecock. “It’s huge,” said McClennen of the win. “I think of the one-designs of this club going back to the New York 30 [built in more


South Pacific Storm Prep

Having set ourselves the task of transforming our recently purchased Open 66 ex-Vendée Globe racer, NV, into a performance family cruiser, my partner, Timo, and I found ourselves (extremely) high and dry as cyclone season approached. The favorite cyclone strategy in Fiji is to more


Cruising: Find Your Own Adventure

Whether they’re at the end of their collegiate career or after aging out of a summer sailing program, a lot of young sailors have a hard time finding a way to continue sailing as adults. Some of the barriers to sailing, including location, finances and time, can be hard to more


Heavy Hitters on Heavy Weather

“What’s the joke about heavy weather? You know it when you see it.” Figure 8 singlehander Randall Reeves drew laughs from the Cruising Club of America (CCA) sailors attending the forum “Heavy Weather Sailing: Bluewater Perspectives” as part of the CCA’s centennial celebration in more


Best Boat Nominees 2023

The more things change, the more they seem to stay the same. Some of it is timing. Some of it is just the way of the world. Either way, it can be fascinating to see the evolution of the boatbuilding industry over the years, as has been evident in SAIL magazine’s annual Best Boats more