It isn’t easy being me. I try very hard not to be me at times. Perhaps that why I attempt certain challenges. Is tackling difficult expedition boating challenge’s me, or is it who I want to be? I do not feel I am particularly superstitious, yet, when it comes to boating, let’s say I take peculiar precautions. I adhere to things with some truth to them for sure. “Red sky in the morning, sailor take warning, red sky at night, sailors delight.” Further, I do not take bananas on the boat for reasons only the ancient Spanish mariners know. When I am in what feels like the middle of the Gulf of Mexico with the wind piping up, cause some damn fool nearby piped up the wind, I search the gray skies for the sharp edge wings of an Albatross for superstitious balance. You know, kinda like feng shui for small boat sailors.

I try hard at not believing in ominous warnings, that take on the feeling of dire predictions, which can, well, sink my very small ship. But superstitious behavior is in the mind of the beholder and if it’s true is it superstitious? I think not, young grasshopper.

You be the judge.

Our 2020 effort started about 24 hours after our EC 2019 finish, but let’s begin this discussion upon our departure from the homeport in Michie, TN on Wednesday before our Saturday scheduled start date.

It is a long single-day drive to our motel near St. Petersburg, Florida. This year we break it down into two shorter days to conserve energy for the pre-start events. It is a hard drive through heavy rainfall the first day to Dothan, Alabama. I am tired and happy to arrive at our hotel. We haul gear to our room and I return to the boat and trailer to perform a routine inspection as I do for every stop. The boat looks good and glistens in the rain. I pat it on its flanks as if it were an Arabian stallion. I walk the trailer, proud of the new waterproof LED lights and the hardening of the bunks and reposition bits and parts that make trailer stronger. I feel the passenger side wheel hub. It is cool and clean. I casually check the other hub and the wheel is tilted on the axle. The hub grease cover missing and grease slung over the wheel. Upon closer inspection, the outer bearing is missing and the wheel on the verge of falling off. The outer grease fitting is missing and the outer ring bearing is not there.

Really? This is Wednesday evening. The boat has to be on the beach Friday morning and I am in a strange town, in an unfamiliar city at 1700 hrs. with a wheel falling off my trailer?

The hotel staff is of little help. I call an auto repair I can see down the road. They suggest I call a marine shop. The marine shop says no problem, we can fix it next week. They suggest a person called Bob, not a company, who might be able to help. He would have this guy call me.

Yeah. Right. I am getting the brush-off. I hang-up and start scouring the internet on my phone seeking some insight into what I might do when the phone rings. Huh. Bob is calling, the guy who might help. He tells me to have my trailer at his shop at 0800 in the morning. I explain the wheel will fall off in about thirty feet of motion. He says call this towing company. I tell him I will need to call AAA, he repeats, ask them to call Eagle Towing. MMmmm. I am just going to let AAA handle it.

I call AAA and tell them what Bob said. They call me back and say that company is closed. AAA calls Phillips Towing who calls me and says he is on the way. but wait, don’t come now, come in the morning. He can store my boat and trailer overnight he says, I say, just come in the morning. Thanks and goodnight see you in the morning.


I need dinner and a drink. There is a Top Chef winning chef in Dothan who has a restaurant I want to visit that has a bar. We call an Uber so the boat and trailer can stay secured to the truck until morning and I can safely indulge.

We sit at the bar, the staff is fun and the barkeep wants me to try a special. It’s a Bourbon Margarita. Gee, that sounds hideous.
It’s wonderful! Keep them coming!

We order dinner and an attractive blonde sits next to me. Guess that the other guy is her husband. Come to find out she is a Director of Nurses at a local hospital and Zeb Owens works for trailer sales as in tractor-trailers. I explain my plight since he is in a slightly related trailer business. He replies, he can’t help but knows many people in the trailer business that can. I explain I have a name of a guy, Bob, with a no-name company in a field outside of town. He says, oh yeah, that’s my friend Bob Downey. He will take great care of you. We have a wonderful evening with our new acquaintances. They are nice people.

OK, smallish town, but not that small, not sure we are going to make the race start, but have no other options but to go with what we got.

Next morning. Eagle Towing shows up at 0800 loads boat and trailer on the wrecker. Wait. No! It’s supposed to be Phillips Towing, but this…is. Aw shit, just take the darn thing to Bobs. Thirty minutes later the Phillips Towing company, calls and says they are at the motel and cannot find the boat. Oh jeez. Thanks, AAA. I explain AAA has called two companies. He is a bit pissed. I tell him to take it up with AAA.

Now my boat is being unloaded in one of several old garages in what could be a Dothan, Alabama beanfield with a faded sign out front that says something like Computer Resales. Bob is very nice. He convinces me immediately he knows what he is doing and then proves it.

Bob explains his company, Wagon Works has been in the same spot for thirty years, doesn’t have or need a shop sign, does not advertise and is constantly busy with a variety of trailer work. None of it has to do with computer resales. One of the things he shared is his work on several Pro Bass fishermen trailers. They come in every two to three months for preventive inspection of wheel bearings.

While Bob is talking, two of his guys have both trailer wheels off and assessing the damage. Bob looks, consults and says, I want to do both wheels with new bearings to make sure. It is 0930 now. Come back at 1130 and you will be good to go.

Wow! He did, I did and he even shares with me a short cut out of town and a great place for lunch on the way.

I LOVE DOTHAN. Thank you, Bob, and thank you, Zeb.

Oh, yes. It rains and the wind blows hard as we make our way to Florida.

Part of my training this year, besides the rowing machine, is preparing and setting finishing goals. I am discontent with our Everglades Challenge finish 2019 when we did not arrive until late Thursday evening—six days underway. Yes, happy to finish, but embarrassed at being so late. This year I have a mantra laid out on paper I recite with every meal.

Saturday Checkpoint One-Englewood.
Sunday Checkpoint two-Chokoloskee.
Monday Checkpoint three-Flamingo.
Tuesday Finish Key Largo.

As it turns out drilling this into my head was a mistake, but first, let’s get to the starting line.

Our effort to set the boat on the beach goes extremely well with lots of help from colleagues. This is always a busy exciting time.

Busy in setting up the boat and exciting meeting old and making new friends and walking the beach looking at a hundred different shaped and sized vessels sitting above the high tide/starting line. I would be remiss if I didn’t confide that before the 1500 hr captains meeting that we have fresh, chilled oysters and beer at Billy’s Bar down the road. Pre-race oysters have become a superstitious indulgence for long life or simply staying alive during this event.

Saturday AM the start is a muddle. There is a three hours delay due to weather and we are given the choice of starting off the beach or moving across the bay to find a start. We elect to start with other sailboats off the beach even though there are high choppy seas in the Gulf and the formidable current in the shipping channel we must cross to get there.

We struggle with our boat rollers at the start.

There is a little dip and hill in the sand and the boat gets stuck there, but finally, we get the damn thing in the water. Kyle piles in, raises the sails while I hold the boat in place and he finishes adjustments. Inexplicably he and the boat start sailing off dragging me behind as I try to move my five layers of clothes and wet suit through the water to get a foot on the aft ladder. Kyle jerks my upper body hard and high enough that I finally get a foot on the ladder and heave the rest of me into the boat where I take the tiller and Kyle moves forward.

The first few minutes are rather a perilous period in heavy weather as it takes us a bit to get “settled” meaning get our shit together, get our collective heads in the game and become one with the boat. We trim the boat properly and try to settle into the boat. We are just about settled, but not quite when we decide to gybe and take up a more advantageous course.

Aside: Many sloop-rigged boats are hard and dangerous to gybe, however a Core Sound like ours with its cat-ketch sail system is much easier and less dangerous, so we have no particular fears in doing a controlled gybe in high winds in this marvelous little vessel, a move we have performed in high winds on the Tennessee River routinely.

Unfortunately, something goes amuck and to this day we have no idea what, and I am not going to speculate what may have happened and why we failed collectively to control the gybe effectively.

Our controlled gybe consists of throwing the helm over and the crew grabbing a fist full of mainsheet line below the sprit as the sail catches the wind on the backside and starts to pick-up force and fly over more than 180 degrees to the other side of the boat.

Now in real-time, the helm is thrown over to gybe and the next thing I know there is a loud pop as the sail comes to an immediate stop at the end of the mainsheet and lays hard against the loose running backstay. We are both startled by the pop but the boat is gybed and sailing—but sailing slower. We look around and find the top five sail slides have broken and the top of the sail is attached only by the halyard and the lower sail slides that remain in the track.


This is not good.

We attempt to return to the start beach which is directly into the wind. The boat will not point into the wind more than about 70 degrees with the broken sail and it is painfully slow going the mile or two back toward the island. We end up well down the beach where a ranger has seen us land. She does not bother to tell us we cannot land here, but rather works out a plan to get us back on a trailer and off the beach out of danger so we can do what we have to do. My four-wheel-drive truck puts the trailer into the water near the ranger station road. The boat floats on the trailer and as I pull it out of the water the trailer gets bogged down in a slight valley and the truck spins its wheels in the sand and gets stuck. More rangers come to our rescue each with a better idea leading to a ranger truck pulling my truck while we both run in four-wheel drive back to the start beach and the safety of the grass behind the beach.

This handful of rangers willingly went out of their way to save our effort and to make it much easier to recover and be on our way. I cannot thank these men and women enough for their help and wonderful attitude.

We get the boat back to grass and down rig it and then go in search of properly sized sail slides. Poor Kyle ends up going to three West Marines in St. Petersburg, Bradenton, and Sarasota to find the number of slugs we need going forth. Kyle then spends the evening, while at a party with local friends of ours, attaching slides to sail. The attachment is as good or better than the originals.

Sunday morning we launch from a small, little-used, county park which I will not divulge as I have used it twice now as an Everglades Challenge starting point. We sail out of Stump Pass into the Gulf after doing our SPOT check-in with Ckpt #1. We follow the coast as close as we feel safe to do while crossing Boca Grande channel and pull in closer to shore as the wind picks up. We reach the end of Sanibel and the winds and seas increase dramatically. We pinch up hard around the island hoping to seek the protection of the mainland south of Ft. Myers several miles distance. There is too much wind and nasty seas. We make no headway.

The wind is blowing 20 to 30 with four to five footers with the required occasional six-footer. We are double reefed and can make no forward progress. We find ourselves tacking back and forth in the same spot off Sanibel. We are beating ourselves up badly so we take shelter in the Gulf where we anchor up behind Sanibel licking our wounds. We pour a shot of whiskey and vow to try again later.

We plan to check the O’ dark thirty weather but do not bother as the wind increases. In the morning we haul anchor and try it again with the same results—back and forth, back and forth with no joy. Based on our calculations of predicted weather it will be Friday before we can get to Largo.

We talk.

Five broken sail slugs put us a day behind. We missed the north wind advantage that would carry us around Sanibel and into favorable coastal waters for the predicted east winds. We replay out loud the two days of rain and wind traveling to Florida. We talk of the trailer wheel falling off. We look at those things as a prediction of things to come. We mold those events until they feed into our superstitions We talk ourselves into calling the race and taking a DNF.

Our bailout option is singular. Sail back up the coast to a pass that is angled and deep enough to allow us to go a bit to windward. The choice is easy. Enter at Boca Grande and sail up toward the Boca Causeway swing bridge and find a channel we can sail up to reach a ramp or marina.

The trip north, double-reefed, on a reach, even sailing very close to the beach, the east wind coming off the land is brutal. We work hard to keep the boat on its feet. Our tools are a combination of turning up into the wind and relaxing our sails, over and over again. We take turns at the helm in an attempt to keep our concentration sharp. Even less than a mile from shore the seas are two to four feet.

We sneak into Boca Grande channel by rounding close to the point of Caya Costa and near reach toward the ICW on the west inside of Boca Grande. That sounds like a simple task–it was not.

We are pushed inbound rapidly on a flood tide while the screeching winds blow hard against the incoming tide. In the mouth of the deep Boca Channel, it forms standing waves that rise and fall almost in place, each like a monster attempting to rise from the sand in Dune. The first few monsters strike fear into the heart of men. But the work of keeping the boat going in a semblance of the right direction, turns the fear into a wash of determination and attention to working each wave, just so as not to get knocked down from one side or to flood the boat with water on the other. We spend an hour, that seems like a day reaching the far side of the pass well beyond our target. Fortunately, there is sheltered water deep enough to allow us to sail north and west back to the safety of the ICW.

In searching for our shore crew we get stuck between a bridge and a hard spot. We run into a large retired railroad bridge house while attempting to get through a narrow cut. The collision is hard, sliding the crew forward at least six inches in the cockpit, this, followed by a mayhem of tangling sails and lines on an ICW red marker. This incident now properly defines the term clusterf—k for me. The final insult was accepting a tow by a passing boat to a nearby marina.

We down rig the boat for trailering. We are exhausted, but I mentally drop into a dark hole of would of, should of, could of.

We could backtrack and take the ICW and chances are we could make the big bridge at Ft. Myers then cruise down the coast and take the tide in Checkpoint 2. Perhaps later catch lighter east winds to allow us to tack to Flamingo. Maybe go around the park boundary in the Gulf then up the ICW to Key Largo.

But for wanting and planning to do the event in four days, I have learned from the Everglades Challenge yet another important life lesson: When one eye is fixed on the destination, you have only one eye to search for the way.

Because of our superstitious behavior—well, there are never enough excuses for quitting–are there. So here I sit like Capt. Brandywine Gage “Rump-sprung and calloused where no man nae’ ought to be calloused.”

Next year’s Everglades Challenge will be approached differently. I will use the anger at myself and the embarrassment of quitting, to re-structure my 2021 Challenge. I will set my plans now. I will finish—no matter the time it takes.
First I will be safe. My challenge will be loose, flexible and consist of working with the elements to my best advantage even if that means sleeping it out or going backward to go around. My goal should always be to finish safely.

Even after all this recrimination, my head niggles back to a single set of thoughts. Sailorman was roughly the same spot and time we were off Sanibel. Could that have been us–lost at sea?

I am not a great writer and certainly know nothing about poetic schemes and the following is not careful, thoughtful, or poetic. It is a desperate attempt at purging some of my emotions over the loss of a person, during the Everglades Challenge, I have never met. It is for a person who I only know as a picture of an upside-down, water ladened boat. A vessel like mine. That blue hull barely afloat in the Gulf of Mexico, to me, is Sailorman:

A Tribute to SAILORMAN.


Sailorman, Sailorman how have you been?
It’s good to see you on the beach looking fit and trim.

Sailorman, Sailorman are you ready for the run?
It will be three hundred miles—three suns or more before your done.

Brother Sailorman are you Challenge prepped and ready for some fun?
For it’s time to leave the endless sands of beach,
It’s time to slip the surly bonds of earth and chase the surging tides.

Its time to slog through oozing mud of Chocolusky,
Its time to seek and touch the basin rim in Flamingo,
And it is time to log a route that takes you to Key Largo.

Sailorman? We hope you hit the spot soon as your track is slightly out,
No doubt you briefly nodded off.
Dude, wake up and resume your route, yes, no doubt you nodded off.


Sailorman, OH Sailorman where have you gone. Sailorman NO!
Do not let this go,
Do not let this be your ‘sweet sorrow’.

Sailorman, we all know and accept the risks, the sea is a harsh mistress,
Yet it is hard to accept dear Sailorman, that you have met her like this.

Our sailorman,
You have reached the ultimate challenge,
And discovered life is a corridor and death merely a door.

We pray thee well and hope your crossing the bar was merciful and quick,
Even as your memory will linger with us all forever and ever, Amen.