Everglades Challenge 2023 – TTG

For the tenth year or so, I invite the Turcopolier Committee of Correspondence to check out this year’s running of the Everglades Challenge. I discovered this event now well over a decade ago. I still have dreams of participating in this challenge or the similar Blackbeard Challenge in North Carolina. The event is organized by a colorful group of adventurers who call themselves the Water Tribe. The Everglades Challenge is an unsupported, expedition style adventure race for kayaks, canoes, and small sailboats. It starts at Fort DeSoto in Saint Petersburg, Florida and ends at Key Largo. The distance is roughly 300 nautical miles depending on one’s course selection. There is a time limit of eight days. Updates on the progress and tribulations of the participants will be posted on the Water Tribe forums. The boats are tracked by SPOT satellite. Their progress can be seen on this tracking map. There’s also a Facebook group. It’s a private group requiring a sign up, but it pretty easy unless you’re a bot or a complete asshole.

In 2020 Rob Waddell, his equally salty compatriot and their spouses made their way from New Zealand to Florida, bought and fitted out a boat and successfully completed the challenge. He said my annual reports on the Challenge inspired him to give it a go. So, even if I never make it to Florida, I take solace in knowing that in some meager way, I’ve contributed to the Water Tribe ethic. 

Rob emailed me yesterday with news of his former “Southern Cross” and her continuing adventures.

The EC300 starts this Saturday 4th March at 10:00. The Dovekie 21 that Johnny Macdonald and I sailed this adventure race in 2020 was sold to Andy Hayward in 2021 as we could not continue our planned three race series due to travel restrictions.

Andy and sailing partner, Nate Vilardebo, have now equipped  ‘Southern Cross’ with a conventional cutter rig with mid-boom traveller in preparation for a go at this challenge. They are keen sailors and I am so pleased that they feel confident with this boat. We all look forward to their progress down to Key Largo.

Winds don’t look too great for Saturday start with a brisk southerly but start veering westerly to northerly from Sunday. By Tuesday – Wednesday it is back to standard easterly in Florida Bay. Light but favorable conditions for the Dovekie. I will follow their track with great interest.

I am most intrigued by another entry. Vladimir Eremeev, aka Crazy Russian, is sailing an 18 foot long shunting proa of his own design called Drama Queen. It has a shallow draft, flat bottomed main hull with fully retractable rudders on both ends. He designed and built it years ago  and is finally ready to give it a shot. In addition to the unique twin rudder design, I was struck by the number of lines used to control her. Simple it is not, but Vladimir is a seasoned adventure sailor and has already completed several Everglades Challenges. The question will be the boat, not the sailor. With my growing interest in shunting proas, I will be watching Crazy Russian’s progress down to Key Largo.

In this video Crazy Russian explains the sail rig on his proa. https://www.youtube.com/watch?v=70MtdPetBo4

Here is that ingenious steering system that also provides needed lateral resistance for the shallow, flat bottomed main hull. https://www.youtube.com/watch?v=39JlbHJr7rU

And here is a view of the whole shunting thing in action. https://www.youtube.com/watch?v=XHuWcjmHufM


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30 Responses to Everglades Challenge 2023 – TTG

  1. Antar ibn Shaddad al-Absi says:

    Just want to say what a great job you are doing, keeping this page going, and what you are posting on the Russian-Ukraine war. We all appreciate it a lot. Wishing Pat well.

  2. Lars says:

    I will follow it closely too. I lived on Estero Island for 18 years and am very familiar with the waters they will compete in. Who ever came up with this “challenge” is a genius.

    • TTG says:


      I think this was the brainchild of Steven Isaac aka Chief. He’s developed quite a following. Seems this year the red tide could pose an additional obstacle.

      • Rob Waddell says:

        Lars . TTG..
        Chief Steve Issaac is competing this year on a Core Sound 17 burmuda ketch. On the watertribe roster comment section his is ‘This is going to be a learning experience’.
        83 compeditors this year so its going from stength to strength. All the best to every compeditor and shore based helpers.

  3. Matt J says:

    I always look forward to the Everglades Challenge post! Almost a rite of spring.

  4. English Outsider says:

    Seconded the first comment. 100%. I’m glad you’re back on the boats. My own exploits in that line are too trivial to mention, let alone amateurish, but I saw a bit of the different world out there on the water and those articles always bring it back for me.

    TTG – hope it’s not intrusive to ask, but how’s the Colonel?

    • TTG says:


      He’s doing fine for a man of his age and life experiences. However, with all that time in and out of a hospital bed, he now requires some dedicated physical therapy to fully regain his mobility. He’ll be back.

  5. Fred says:

    They are being met with 30 knot winds again this weekend, which is unfortunate. Last weekend the weather was perfect. Best of luck the the participants.

    • TTG says:


      Chief already made the decision to allow “Plan B” launching south of Tampa Bay because of the winds. There’s ten or so boats still on the beach at Fort DeSoto who will launch from there. Both the Southern Cross (21′ Dovkie) and Drama Queen (Crazy Russian’s proa) remain on the Fort DeSoto beach.

      • Fred says:


        Sarasota bay had about a 4ft chop when I posted my comment. It’s still windy but it looks like it has smoothed out. (Ft. DeSoto is about ten miles N of me.) Otherwise a beautiful day.

  6. TTG says:

    They’re off. This just posted on their Facebook page along with several videos of the beach launch.

    “And they’re off. Great conditions developed overnight and a more westerly 15mph wind made for reasonable launches off the beach. Interesting staggered launches. Generally when the horn blows everybody launches at the same time. Anyway about 1/3 of the participants choose Plan “A” and launched off the beach (almost 30 I think).”

  7. Chrisitan Chuba says:

    I would love to do something outdoors and meet people who I have corresponded with. But currently I am selling apples on a street corner (illustration, not literal). I am convinced that people would be more civil to each other if we met in person rather than just reading posts. I am not accusing any of being rude to me here. I have been treated very well.

    I like moderately cold weather. I do not hold up well in the heat (Slovak trait?) BTW if you use a Kayak, I learned the hard way that having a good rudder on open waters is very valuable. Kayaks are nimble in waterways but on open waters you can waste a lot of energy trying to keep it moving forward.

    • TTG says:

      Chrisitan Chuba,

      In general, people are more civil in person. Maybe it’s the lack of anonymity to hide behind or the remote chance of getting punched in the mouth. But people brought up right and possessing some degree of courtesy and self-discipline should be able to be civil to others in person or online. Colonel Lang and I first became acquainted online on his old SST blog. Later we met on the shooting range. We don’t agree on everything which led to being temporarily banned once and losing writing privileges another time. But we never engaged in a brawl or name calling. That’s beneath both of us. It should be beneath all of us.

      I know what you mean about kayaks. Mine is just a plastic recreational model, but it tracks well paddling without a rudder. I made a sail rig for it with two small daggerboards for lateral resistance. Weight shifting and using a paddle as a rudder control the tracking.

      • LeaNder says:

        TTG, I spent a lot of time on PL’s blog. Way too much, really. After all these years curiously enough once upon a time fleeing post 9/11 conspiracy theory circles to wind up after a couple of years with conspiracies migrating right into the center, in the form of a series of real US political conspiracies some via pizza connections.

        Thus, I initially watched people banned over and over again for the simple corpus delicti of appearing too liberal/left leaning. I would assume the troll wisdom as discussed on TTG in that context, close to comma rules, was as widespread as ultimately useless. Trolls are simply and will be whatever type of outsiders as perceived by insiders from within their bubbles. Including the professionals: Hey, where can I apply? (semi irony alert)

        But that you were banned too escaped my attention. Also, that you lost writing privileges. Why and when was that? Might help ot change my mind. Superficially you of course fitted the profile.

        • TTG says:


          It was during the heat of the political campaigns. We both passionately supported opposing camps, but this is Colonel Lang’s blog and he was not comfortable with the passion of my anti-Trump rhetoric. Issuing a temporary ban was his prerogative.

          • LeaNder says:

            Yes, I vaguely seem to recall now, he indeed may have banned you, but only shortly. An exception for the brother in arms, in spite of his not quite so good career choices? 😉

            not comfortable with the passion of my anti-Trump rhetoric

            Not sure if I may, consider it private if you like: Strange to watch, he initially did not endorse Trump in probably one of the oddest campaigns ever. Sure, he liked his politics. But how can you endorse Sanders and then call “Sleepy Joe” a communist/socialist threat. I still don’t understand? The Squad threat? Sanders was no such threat? Yes rough times and crazy to watch even Walrus, never ever would I have expected him or Babak to become targets.

            I doubt I was ever passionate in my anti-Trump rhetoric, but felt I had to add my “cultural Marxist” as counterpoint to the trend, purely rhetorically. Were have all the classicists gone? 😉

            I was deeply puzzled how my ironic comment that maybe Trump simply was tired of waiving the recognition of Jerusalem as the capital of Israel every half year as the Jerusalem Embassy act forced him to. That was lèse majesty? Or Anti-American? Ok, maybe, for the ardent patriot supporting his CIC. …

      • Chrisitan Chuba says:

        “I made a sail rig for it with two small daggerboards for lateral resistance”

        That looks like a good configuration.

        BTW recommendation to all. If you ever get a chance to operate a one man sailboat, like a Sunfish, do it, do it, do it. I got to try one at my son’s camp and it was great. I mention is because I always thought sailing was for expert yachtsman but it isn’t. The guy at the dock gave me one 5 minute lesson on how not to kill yourself and that was it. I made mistakes but eventually figured it out.

        There is nothing like catching a good wind on a sailboat. I think men are wired to enjoy, ‘light physics’, watching a golf ball you hit curve in the air, figuring out how to catch the wind with a sail, … I encourage woman to explore this as well, this is just an observation.

        • Leith says:

          I’ve messed around in canoes, flat-bottomed punts, kayaks and 16 foot V-hulls. As for sailboats, all I know is that those are the one with sticks pointing up. And don’t they have to travel √2 times the distance that a normal boat would travel to get where they are going?

          • Chrisitan Chuba says:

            It’s all about catching the wind.

            I was on a lake and didn’t care where we were going. I just enjoyed figuring out how to angle the sail to maximize speed. I found the unpredictability of a wind gust exhilarating.

            Just saying that if you are on a windy lake or open body of water, it requires very little muscle to use a sail. You might zig, zag a bit but if you are on a windy / choppy lake paddling becomes difficult.

            TTG’s configuration looks great. Paddle until a wind kicks up, then switch to sail.

          • TTG says:

            Chrisitan Chuba,

            I got the idea for my sail rig from this video. I think it’s the best of all worlds. Cheap. Light enough to hoist on the car and carry to the water by myself. Useable whether the wind blows or not. Floats and sails in inches of water and, with a spray skirt, handles some pretty hellacious waves.


          • Chrisitan Chuba says:

            TTG the cams a bit shaky but I get the basic idea. You add two cross boards to mount the sail and the dagger on each side. I don’t know how those boards are mounted, clamps or screws? I would think that you want to avoid drilling into the Kayak as much as possible.

            It’s a really cool idea, I can always dream.

            Never used a dagger board, if you have one on each side do you ever just lower one or do you always do both at the same time?

          • TTG says:

            Chrisitan Chuba,

            You only need one daggerboard at a time, but I find it far easier to pivot them both down when i start to sail and leave them down. These dagger boards are small, bolts and friction are enough to hold them down. I only had to drill holes to attach a tiedown loop on each side of the hull to tie the entire sail rig down, not obtrusive at all.

  8. TTG says:

    Updates from earlier this morning from Drama Queen and Southern Cross.

    From Crazy Russian, “I sailed to stump pass and decided to wait. Moon is down. It’s an hour to sunrise and tide shift. Not enough wind to power through. And low tide. I guess I will wait. It was a slow day beating upwind.”

    There’s a video by Nate Vilardebo of Southern Cross in the bestilled in the darkness along with a comment, “Andy was hit the neck by a flying mullet last night at full speed. That’s gonna leave a mark!”

    Ah, good times.

  9. TTG says:


    Southern Cross and Drama Queen passed through check point 1 earlier today and are well on their way to Chokoloskee (CP 2). Two very different boats, but they’re generally keeping pace with each other.

  10. Babeltuap says:

    Putin stated he intends to push them back past the point they can strike the new Russian territories. Think it’s 150 km right now so that would be the end of the war unless they get rockets that strike deeper then it will continue.

  11. TTG says:

    Everglades Challenge Update

    Crazy Russian has stopped about 10 kilometers outside Chokoloskee. He maybe waiting for tides before threading the channels into CP2 or he just needs a rest. Andyman and Natedog arrived at CP2 earlier this afternoon and are now on their way to Flamingo (CP3). They’re all doing pretty well. I have to admit, a crew of two on the Southern Cross is surely a lot dryer and cushier than single handing a small proa. There’s no rest for Crazy Russian unless he lands somewhere.

  12. TTG says:

    Another Everglades Challenge Update

    Andyman and Natedog, sailing Southern Cross, arrived in Key West earlier today completing the challenge. They made damned good time and made a bold move of taking the shallow, but direct route from Flamingo to Key West. Some of the Channels were said to be 7 inches deep at best. Congratulations to the both of them.

    Rob Waddell told me a couple of years ago that boats like the Dovekie 21 were ideal for this challenge. He knows his stuff, obviously. There was also a comment on the Facebook page today to the effect that the previous owner (Rob) of Southern Cross sailed it like he stole it and wore out the original sail in 35 knot winds. Well, ya do what ya gotta do.

    Crazy Russian in Drama Queen, his shunting proa, arrived in Flamingo (CP3) this afternoon. He’s already broken records for shunting proas in the challenge. It’s even more amazing that he’s doing so single-handed. He’ll be in Key West in a day or so.

  13. Rob Waddell says:

    ‘Sail like I stole it.. ‘ definitely and every time, and it was was trial by fire for Johnny Mac, a first time sailor as well in 2020. But I didn’t break the rig. Southern Cross was chartered to another sailor in 2022 but they wrapped it around a marker post on the south passage in Florida Bay and retired on this last stretch. I admit to wearing out the original sail though.

    Anyway its well done to Andy and Nate. They are long time competitors and know the track well, especially the back roads.

    Supreme result from Crazy Russian. To design and sail a complex vessel like his shunting Proa ‘Drama Queen’ requires serious skill and fortitude. A great sailor.

  14. TTG says:

    Crazy Russian Update

    He sailed into Key Largo early this morning. First shunting proa to complete an EC. He wrote this after coming in.

    “Thank you all! It was quite a trip 🙂
    To answer all questions.
    I built the boat for 2014 EC. Unfortunately life got in the way of boating right about the same time.
    I launched the boat first time 6 hours after the start of EC in 2014, sailed her almost to first checkpoint, turned around and sailed back. I shelved the boat for 8 years. Last fall I decided that I need to finish the boat and I had been working on her through last winter.
    This is my second attempt to sail a proa in EC and first successful.”

    Crazy bastard lives in Maryland with access to the Chesapeake. I ought to look him up. You know. One crazy bastard to another.

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