A Early Start to Everglades Challenge 2023 Training

At 7 am, Chief gave the signal: the Everglades Challenge had begun. To my left and to my right, kayaks, sailboats, and one paddleboard launched into Tampa Bay, beginning the 300 mile journey to Key Largo. Despite my excitement and preparation, I stood on the beach, intimidated by the wind. The wind rose, and Chief offered me a Plan B start, meaning that I could start further south. I wasn’t sure how far I could go or even if I was still in the race, but after months of practice and training, I was grateful to be on the course.

I launched mid-afternoon onto Charlotte Harbor from Burnt Store Marina, a place I knew from a previous Sup and Sail trip with my husband Kevin. I hugged the shore as best I could, but any exposure gave me a taste of the larger conditions I had avoided.

I passed Matlacha at sunset and continued south as darkness fell, heading for Cape Coral and points beyond. Even though navigation was straightforward at this point, the darkness played tricks on me—at one point, I wondered if I was actually heading north. I never realized that Pine Island was so long!

Finally I reached the mouth of the Caloosahatchee River and a decision point. Given the easterly winds, I wasn’t sure I could hold my course, and the bay seemed like an awfully big place at night. What I knew rationally was the bridge to Sanibel seemed lit up like a casino, and the twinkling lights marking the different channels disoriented me (and confirmed that I need new glasses.) Even though I had only paddled 21 miles, I decided to make camp and navigate the crossing in the daytime.

As I lay awake at 3 am, listening to the tide lap inches from my bivy, I reflected on what went right and what went wrong. What went right? In the weeks before Watertribe, I winnowed my gear, lightening my load, and repacked it more efficiently, for example, my night paddling kit in a separate bag attached to my duffel. I had tested some of these systems on a trip to Panther Key where I met up with members of both Watertribe and West Coast Trailer Sailors and received some very welcome advice.

What went wrong, or better put, lessons learned? More wind practice. I felt strong enough to push on, but a windy crossing in the dark concerned me. I knew that this was the western end of the Okeechobee Waterway, where boats cross Florida from the Atlantic to the Gulf, and images of barges and freighters filled my head.

When I launched the next morning, small fishing boats rather than the massive cargo ships of my imagination dotted the becalmed seascape, and I crossed without incident to Bowditch Park in Fort Myers Beach.

My Sunday morning dreamscape shattered on the ICW in Fort Myers, which gave life to the term wind tunnel. I fought my way under the bridge and used the hulking steel boats as wind shelter. It pained me to pass Randy Wayne White’s Doc Ford Rum Bar and Grill, and but I knew that Doc Ford would just keep paddling. So I did.

In Estero Bay, a parade of pontoon and other boats streamed by, and I bobbed along in their wake. My board felt especially unstable, leading to several unplanned exits, and I didn’t confirm until that night that my fin had disappeared somewhere in Estero Bay. I sat down and paddled, and that led to another lesson learned: sitting works too. Once I was no longer a human sail, my speed increased, and paddling seated should help me handle bigger winds. But as my friend Kathryn helpfully noted, “Some people call that a kayak.” Point well taken.

Later I passed several fisherman who asked where I was going. I replied Wiggins Pass, the first thing that popped into my head. One said “That’s far, it’s windy” and asked if I needed a ride. No thanks, I’m good. And it was. One thing I love about the Everglades Challenge is the self-reliance it demands. I was alone, on a board, on a rocking and rolling Estero Bay. Whatever came up, I just needed to figure it out.

I continued towards Wiggins Pass, wending my way through a series of small channels. A tiki bar loaded with revelers motored by, and another sat anchored in the mangroves. If there ever were an epic illegal camping spot, that would be it. And I paddled on. I reached Wiggins Pass just as Flipper and Foco arrived, happy to share the spot with other tribers. Again, my skill rather than fitness prompted a stop. Once I left the pass, I would be in open water, and there were few, if any, camping options until Gordon Pass. Looking back, since the wind tended to drop at night, I would take advantage of that.

The next morning, I attached my spare fin and aimed for Naples. Rolling waves pushed me for the first several hours, until the winds rose up again. I entered Gordon Pass and fought my way through Dollar Bay towards Marco Island. There I made my final mistake.

At Panther Key, Andy said that if you have an out, you’ll take it. As I paddled towards the Marco Island, Kevin appeared in a kayak. It was just too easy. And that led to yet another lesson. I spent too much time on Windfinder, obsessing about predicted winds. My mistake: looking too far ahead. With some rest, I could have continued and taken advantage of diminished winds. Focus on the present.

2022 was my first attempt at the Everglades Challenge, or perhaps, a head start for Everglades Challenge 2023. (If only it counted for next years derby.) It was a terrific experience, and now I know better where to focus my training. In retrospect, I could have crossed Tampa Bay, and I have paddled successfully in bigger conditions, but I need to do it more of it. Even though some said we faced especially difficult headwinds this year, it seems like it just isn’t an Everglades Challenge without them—unless you’re going the wrong way. So, my prescription for myself: wind, waves, and open water crossings. And see you on the beach next March.