The Everglades Challenge is a 300 mile boating adventure that happens every March. A bunch of crazy people pay $350 to show up on a public beach and sail, row, and/or paddle 300 miles from Tampa Bay to Key Largo risking hypothermia, exsanguination by voracious mosquitoes, drowning in a violent storm, and etc all on free public waters. For all of this, they get a shark tooth and a toy paddle both of which can easily be purchased at any one of a thousand tourist shops. This will be my fifth time shelling out this money for the possibility of getting said trophies. Why do we do it? For the privilege of hanging out with other crazy people, for the recognition, and for the safety in numbers. Heck, I can spend more just getting a beach front hotel room for a couple of nights ordering room service but I won’t get near the satisfaction.

As can be seen by the captions, I attempted the Everglades Challenge four times before and only completed it once. It isn’t called a Challenge for nothing. You have to choose the right boat, be mentally prepared, and be patient to complete a challenge. This all assumes that nothing catastrophic happens to you or your gear.

In 2011 I attempted the challenge solo in a homebuilt 12′ catboat I had equipped with a dodger to sleep under and keep out the spray. I was not ready mentally not having had enough experience sailing in a small boat in rough weather conditions. I sailed through the night and faced some very rough weather on the nose near stump pass and made a snap decision to drop out. Never make a decision when you have had too little sleep! I also discovered the disadvantage of overpacking…can’t find what you need when you need it!

In 2012 I attempted the challenge in an eight foot Puddle Duck Racer I had built specifically for the event. I had a dodger that covered the cockpit giving me a dry place to sail from and to overnight. Again, it was a tough weather year with very few Class 4 sailboats finishing. I was in the middle of the pack when a sudden violent gust caused a capsize in the Gulf of Mexico off of Naples, FL. I lost some of my gear having not tied it in for fear of getting tangled. I also had rarely ever capsized a boat so dropped out despite recovering with only inches of water in the bottom. I deeply regret not having picked up replacement gear (clothes mainly) and continued on winning class 4 single. I just didn’t have enough experience.

In 2014 I successfully completed the Challenge with John Bell (aka Mister Moon) in his Core Sound 17. It was a very light wind year but, with the help of an old stained sail I made into a mizzen staysail, we were able to keep moving at a decent enough speed to finish. I also learned how nice it was to have another person on the boat with you.

In 2017 I attempted the challenge with Scott Gosnell (aka Foghorn) in his 13 foot IMB. This is an interesting boat designed to be sailed from inside the cabin with a slot-top that provides a cooling breeze or can be closed off to protect from the weather. We made the decision to go on the gulf side (leeward side) of Sanibel Island on a high wind day. We were gambling that the wind would die down before we had to cross open water. Unfortunately, the wind failed to die down, the waves were towering over the boat, and our sail was starting to rip. Scott Gosnell was also feeling the effects of life stress and an oncoming cold so we had to drop out. This was Scott Gosnell’s 2nd failed attempt to earn that sharks tooth.

At this point in my life, I had decided that I could easily go and enjoy the beautiful coastal waters without having to shell out the $350, during a better time of the year, and in a powerboat. In 2021, the Everglades Challenge happens the same week as my Spring Break (I am a college professor) so I could go down and enjoy the festival without any guilt. I called Scott Gosnell (aka Foghorn) to see if he wanted to join me in doing the route, but not the challenge, in my 1952 Lone Star powerboat.

I thought I had a brilliant idea as my boat cruises at 20 mph going 9 miles per gallon. We could choose when to be on the water and have some fun visiting with our friends in the challenge while on the water. Scott Gosnell, on the other hand, had other ideas. He has yet to earn his Sharks Tooth and wanted to be a participation and not a spectator for the challenge. Something in me must have agreed with him all along because next thing I know I am volunteering to do the challenge with him in my newly acquired Com-Pac Picnic Cat. Not only that, but I am more excited about doing it the slow and more costly way to boot! Of course, when seeking spousal permission I couched it as “helping out a friend” when truly I am excited to go.

Why do it in a Com Pac Picnic Cat you might ask? Well, in 2014 I enjoyed the size, freeboard, and stability of John Bells (aka Mister Moon’s) Core Sound 17. We also met up with a SeaPearl several times on the route and it got me to thinking about comfortable sailboats that could be beach launched (one of the “filters” for the Challenge). At the time, I was the happy owner of an easy to launch and sail Com Pac Suncat, a 17 foot catboat (single sail) with a cabin. This boat, with its full keel and 1500lb displacement, was not able to be launched from the beach but I knew if its little sister, the 14′ Picnic Cat, that could do it. The Picnic Cat has a displacement of 500 lbs and a centerboard that fully retracts into the hull for a minimal 6 inch draft. Best yet, it has a lot of stability and a large self-draining cockpit. In other words, since 2014 I have been thinking it would be fun to do the challenge in a Picnic Cat. https://sailboatdata.com/sailboat/picnic-cat-com-pac

Fast forward to 2019 when I found myself in need of a sailboat for our newly purchased home in Pensacola. I had lost a suitable boat when our house had burned down in April (Otis, my 14′ self designed and built boat). The launch ramp near our house requires going under a 15 foot clearance bridge if you want to get out to Pensacola bay. Few sailboats of any size can pass under this clearance and most sailboats are difficult to raise or lower the mast while underway. Com Pac makes a line of catboats with tabernacle masts that makes raising and lowering on the water very easy. I had owned a 17 foot Suncat before and regretted selling it but I wanted something a bit smaller and lighter. Fortunately for me, I was able to snatch a Com Pac Picnic Cat off of ebay. Had to drive to Charlestown to pick it up but was well worth the trip! This is why I just happened to have the right boat at the right time!

When I brought the Picnic Cat home, I made some changes like like taking off the big “Downsized” name and re-christening her “Catnip.” I also cleaned her up, gave a fresh coat of bottom and bootstripe paint, added a bimini, and switched to a two-part throat halyard. I have very much enjoyed getting to know this boat and continually tweeking it for the type of sailing I like to do.

Now that I introduced you to the Challenge, my reasons for doing it again, and the boat I intend to do it in, I will close out this chapter. Next posts will detail our preparations for the 2021 Everglades Challenge.