New Orleans, Louisiana – March 26th, 2024 – Years before I even conceived of doing NY to SF on a proa, I wanted to do the Everglades Challenge. I’ve thought of many different boats for the challenge and thought it would be a good idea to do it as crew or on something more conventional first to get a lay of the course. Ultimately, I ended up with a conservative, albeit very lightweight trimaran for the event and was actually very happy with the choice.
Now, for anyone who has been watching this event with envy or trepidation for years, I want to demystify some things for you here based on my one-time experience.
This is not a sailboat race. It’s harder. You don’t need the fastest boat to do well in this event. This is a race between checkpoints, the checkpoints being where the real gains and losses happen. You must have a boat that rows, paddles, or peddles easily if you want to be competitive overall. (My boat didn’t really paddle very quickly with a lot of wetted surface area and windage, and controlling the heading while changing course singlehanded was very difficult. I’m not sure what I’ll do about this for next year.)
You MUST be able to sail in 6 inches of water. There are long stretches, especially at checkpoints 2 and 3 where there is very little water. If you cannot kickup your rudder ala Hobie Cat AND still steer the boat, you will be really limping through these stages. (I had a kickup rudder on the main hull which drew 2’3” and the kickup part failed immediately after the start, requiring me to go into the water and reconnect the rudder every time the water was deep enough. This occurred about 8 times during the trip. In my case I couldn’t steer with the rudder kicked up, so I made a shallow draft rudder for the starboard ama to help, but it didn’t offer nearly the amount of control necessary for this course and I often had to take the mainsail down or depower it to keep the boat under control, while dragging the main rudder behind the boat by its steering cables until I was in deep enough water to reconnect it. No way will I be doing it this way next year.)
The charts for Stump Pass, coming into CP1 are not helpful. This is a local knowledge situation and with current flowing in either direction, it can become very difficult. Charts for the rest of the checkpoints are also a grain of salt situation. Nothing beats going out there and seeing them all in person.
If you don’t have time to survey the course prior to the race, just do like I did and survey it by grounding your entire way through and sign up for the following years event 
Tribe names: to find out about the race you must register an account on www.watertribe.com. At the top banner you will see something called “discussion” which means forum. There you must also register to post. HOWEVER, the name you sign up with cannot be your real name and whatever you put down will be your tribe name FOREVER. I heard several times participants who were like “why did you pick that name” and they were just like “I needed something to sign up with and I didn’t realize it’s permanent.” It is. So choose wisely. It doesn’t matter what you name your boat, they will track you by your tribe name, so you might as well name the boat the same thing or visa versa. It’s nice and confusing for your family members who are following the race looking for your boat name or your name only to discover later they were following the wrong boat ,etc… This is simply the way it is and that’s that.
The start:
At the start I was a little slow off the beach and when trying to lower the kickup rudder system (my design), despite having tested it for many miles prior to the EC, it immediately broke off. Oh well. So, I hopped into Tampa Bay, reconnected it with its retaining line and started heading on a close reach to exit the Bay at Anna Maria Island. After deploying my Code Zero I quickly sailed through the fleet and had a comfortable lead by the time I was at Anna Maria. I was hoping to not be leading there because the charts for the area don’t really show what’s happening and I wanted to follow a more experienced boat. I conservatively went offshore to clear the shoals before heading back on course. The boat Spawn was the next boat out of the bay, and they cut a corner I knew was there in research but didn’t have the confidence to test considering my rudder situation. From there it became a very light wind beat to Stump Pass. For the first part of the morning, I stayed offshore, tacking in to cover the boats nearest. By mid-day I split and went offshore, while the crewed boats short tacked near shore all day, likely dodging more North flowing current than me, but it felt more stable offshore. By the afternoon it was clear that I had lost a lot of ground to Spawn and started seeing more boats behind me. However, it still felt bad inshore and was shifty, so I went back offshore making a very favored tack to Stump Pass late that evening and taking the lead again. Pitch black at Stump Pass, I tried using the charts I had to negotiate it, but the light wind and current flowing out really became confusing and I was swept onto a shoal quickly once close to the entrance. I spent the next hour or so running aground, letting the rudder pop off and being pushed back into the Gulf by the current. Then jumping in to reconnect the rudder and trying to sail in, only to have the same thing happen again. I tried pulling the boat against the current off a shoal, but that quickly became dangerous. During this time, I watched Spawn, the Inter 20 (Bump and Tern) and Hobie 16’ (Tenzan and Midnight Crew) pass me in that order. I had no idea how they got through at the time and ultimately used my anchor to kedge into the channel, then reconnected the rudder and paddle to CP 1. I took my time there cleaning the piles of sand and seashells off my boat, fixing some sail furling problems and borrowed a new SPOT from (Mr. Moon) who lent me his Spot device after mine had completely stopped working due to all my swimming activities. He later told me that the SPOT doesn’t have to be attached to my life jacket, which I was unsure of from inspections.
Leg 2.
No wind on departure, at least within the intracoastal waterway leading to Gasparilla Pass. I paddle for a while, then decide to simply drift down the canal and take some naps until some wind arrives. Several additional boats pass me here, but I’m not very concerned about that. Due to my rudder handicap I’ve resigned myself to using this race as a survey of the course. Around sunrise, a little wind fills in and I start sailing again, following Apeman and Janseaka on a Nacra 5.7 catamaran through the channels to Gasparilla Pass. They pull up onto the beach at Port Boca Grande and I continue over the shoals with my rudder down, hoping I skirt over them without problems. I make it into the channel gybe several times and I’m back into the Gulf and alone. I spend the rest of the day sailing upwind in very light wind, with a nice fat tack offshore before coming back to the south side of Sanibel Island, near Fort Myers. There the wind dies completely. I decided I can paddle for an hour and go one mile or get some sleep. I usually chose sleep. I wake up after sunset to a slight east wind, unroll the Code Zero and start reaching quickly toward Marco Island, roughly 30 miles away. Soon I have the Code Zero down and am jib reaching at 11 to 15 knots directly on course in flat water. It’s the best sailing I have during the whole race and I’m very quickly south of Marco Island and tacking through Cape Romano Shoals on the approach to CP 2. By sunrise I’m in Indian Key Pass and short tacking like a maniac with an incoming tide and some very narrow channels. I get stuck a couple of times, but there’s enough wind to sail, so I refuse to paddle. I see Tanzen and Midnight Crew coming up behind me, clearly motivated and paddling. They tell me later that I passed them on the beat to Indian Key Pass. As I’m getting into Chokoloskee Bay I see Bump and Tern leaving the checkpoint, so I’m still in this race to some extent. At least I don’t have a boat speed issue while sailing. On port tack across the bay, my main rudder whacks the bottom and I stop. I let the rudder break away again and drag it to the checkpoint with the little rudder doing whatever it can to keep me on course. There Tanzen and Midnight crew pop in right behind me and have a pretty quick turnaround, me a bit behind them.
Leg 3. It’s downwind leaving CP 2, in very light wind, and I take the mainsail down to keep my little rudder working without weather helm. Instead, I sail out with a jib only then the Code 5, through Everglades National Forest and it is beautiful. I hear wild birds and see sea turtles all the way to Demijohn Key. There I jump back into the water and reconnect the rudder. For newbies like me, the bottom here is all oysters, no sand. Now the wind is extremely light. I paddle to build apparent wind for the sails to work and see Tanzen and Midnight Crew well on the horizon to my south. I take a nap in the hot sun and wake up to a slight north westerly wind, which is not expected, but welcome. Now I can sail again and unroll the Code 5, sailing fast with what wind I have, and I start making gains on Tanzen/Midnight Crew. Soon they are well to my west and by the afternoon, off my aft starboard quarter with a spinnaker up. I’m happy with my boat speed, but I know they are sailing the hell out of that Hobie 16. I couldn’t believe how fast they had been through the whole race. By night fall, I’m beating into a strong east wind around Cape Sable and having some problems with my tiller, the bolt holding it down having to constantly be retightened. This is annoying because the autopilot rudder reference unit must be unbolted for access to the tiller bolt and by the end of the race, I had a quick release method in place with zip ties and one bolt. It got quite bad. I reefed the mainsail and sort of limped into the channel for checkpoint 3 at Flamingo Key. This was the worst checkpoint for me, and I spent hours in waist dep mud trying to drag the boat into the channel only to realize there really isn’t a channel, just markers. Forget your charts here. It’s awful. I then paddled very slowly into the checkpoint having already been passed again by the Hobie 16. I wasn’t too bothered since myself, the boat and sails were covered entirely with mud and aggravation. Wet inside my gear with sweat and saltwater I finally made it into the marina where I demanded a hose to clean the boat like a little princess. The folks there had done the race and were very tolerant of my wet cat behavior. They told me that nobody was close to me, so it would be a good idea to rest there and honestly, I was feeling a little hypothermic, so I wore my wet gear under a tarp and fell asleep with an alarm set for half an hour. Half an hour later they convinced me to stay until sunrise and I did it happily, wanting to see the last part of the race in daylight for next year. I probably slept for 5 or 6 hours and felt great! I left at sunrise and paddled out with my rudder dragging behind me again, reconnecting it off Murray Key, then sailing the long way around heading due West into the yacht channel. This is the only time I used my spinnaker for anything other than a pillow during the whole event. Very choppy upwind conditions after making my turn and it quickly became flat water sailing again with good pressure. I had to do some short tacks through Bowlegys and Steamboat Channels but was able to sail directly through the rest on starboard tack almost all the way to the finish. Perfect and easy sailing really, often making 10-12 knots and comfortable. Once through the last channel, Baker’s Cut, I began looking for the finish beyond the anchorage off Sunset Cove, Key Largo. Easy to spot with all the hands waving from shore and I made one tack in the large wind shadow of Key Largo and paddle-sailed to the beach for my finish. There were kids yelling and people clapping, me standing on the port ama like a dazed fool, boatlenghts from the beach. Then there was a huge bang beneath me and an explosion of water all over the place. Shocked and confused af first I assumed the boat decided to explode at the finish then told myself it was a manatee, however the people on the beach told me it looked more like a very large fish. I assume a tarpon or shark. Either way, no damage and I finished the race at sunset, and it was beautiful. I was the 4th boat to finish and first single-hander by over 31 hours, so pretty content for a first shot at this course.
These types of events start off as races when you sign up. By you finish you realize they’re about surrounding yourself with a community of freaks willing to do these kinds of things and having a good laugh about it after it’s over. A tribe of nuts. In the end, the community is the reason the Everglades Challenge is still going on and the reason I will be coming back next year.
Thank you to the event organizers, participants and my sponsors.
#sailsforsustenance: SFS repurpose used sails for the fishermen in Haiti who use sailing craft to go well into the ocean to provide for their families. Please contact me if you have sails to donate to this cause. As hard as the Everglades Challenge seemed,it’s absolutely nothing compared to the challenges faced by these families.
#ColligoMarine : They provided all of the standing rigging for my boat in this event. Having used their rigging to sail around Cape Horn on Jzerro, I knew there was only on company I had complete trust in for this race.
#Maptattoo : their navigation tablet, designed specifically for races such as the Everglades Challenge and Race to Alaska worked perfectly. The unit is waterproof, holds its charge for 50 hours and has a screen that is easily viewable in broad daylight. Maptattoo was 90% of my navigation during this event and the only thing powered on when I finished.
Photo Credit – Paula Martel