Punta Gorda to Cayo Costa by SUP and Sail

Tuesday: In the early morning calm, Kevin and I launched boat and board from the Laishley Marina in Punta Gorda, Florida and headed southwest toward Charlotte Harbor. Destination: Cayo Costa and our first trip with the West Coast Trailer Sailing Squadron (WCTSS). Blissfully unaware that those “firsts” would keep piling on, we aimed for our first anchorage, just outside of Pirate Harbor on the eastern side of Charlotte Harbor.

For the past several years, Kevin and I have used our SUP and sail trips to develop individual and team skills. Our increasingly longer and more difficult journeys have pushed his sailing and my paddling boundaries in areas of navigation, endurance, and rough water skills. Once again, this trip of firsts would test our skills.

Before we left home, we plotted out our respective journeys. On my 14′ Bishop A’u paddleboard, I anticipated a 12 mile paddle, hugging the shore and ducking into mangroves for wind protection. On our 22′ O’Day sailboat, Kevin’s sail would be considerably longer, given the projected wind direction and the number of required tacks. We planned to meet at the anchorage around 3 pm.

Once I rounded the ‘hump’ of Punta Gorda, the predicted southerly winds arose. Kevin called me on the VHF radio, thrilled at his 6 knots of speed. Thrilled did not describe my mood as I battled against some of the stronger gusts. I ducked into the mangroves, and my chart, GPS, and Fenix watch helped me navigate a path through this very creepy mangrove maze. Shortly after our designated time, we dropped anchor and set in for the night.

Wednesday morning, we paddled and sailed 12 miles to the Burnt Store Marina where we had booked a slip for two nights. Our chance to power the boat’s systems for our anchorage in Pelican Bay on Cayo Costa. Our timing was impeccable and lucky—big winds kept us off the water the following day.

Cayo Costa ho! Friday morning, I awoke eager to begin the day’s paddle. I faced several highly-trafficked crossings, and and I knew I had a short window before the wind came back up. In retrospect, the trip from Burnt Store Marina to Cayo Costa turned out to be one of my most difficult paddles due to wind, waves, and boat traffic. Surprisingly more difficult even than the 25+ mile training paddles I had done. Shortly after leaving the marina, I headed southwest towards the entrance to Bokeelia, an approximately 6-mile crossing. The sidechop and occasional breaking waves challenged my board steering as I struggled to maintain my heading. My early departure had paid off—the wind didn’t pick up significantly until I had almost reached the other side.

I followed the channel markers across the north end of Pine Island, past Jug Creek, Back Bay, and finally Little Bokeelia Bay where I saw several boats from the WCTSS. Finally, my destination was near. From Little Bokeelia Bay, I would paddle south of Patricio and Mondongo Islands, cross the ICW, and head slightly north to our Pelican Bay anchorage.

By this time, the wind had picked up, and each of the short mile-long crossings was a slog. I have never worked so hard just to see my Garmin watch read 0.0 for speed. For safety, I crossed the ICW south of my destination, meaning both that I had to battle the north winds to the anchorage and that final mile expanded to three. My three hour mile. Though at times I doubted if I could make it, I knew I had to. I stopped on a small key, revised my route, and powered on.

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Never have I been so happy to reach an anchorage. We laughed, relaxed, and visited with friends, old and new. A perfect end to a crazy day.

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Saturday was beautiful. Some explored Cayo Costa, and others sailed around Charlotte Harbor and around Boca Grande Pass. I discovered lagoons with manatees, and the spring breakers discovered our paradise.

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By the late afternoon, the winds has risen, and the temperatures fell. The cold front had arrived. Why didn’t I bring socks? Thank you Kevin.

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Our next “first” was almost upon us. We anchored our shallow draft boat just off the beach, as we had the night before. One anchor in front, another astern. Several hours later, after dark, our mistake became apparent as the boat listed sideways. The north winds were blowing the water out of the anchorage, and we almost aground. We rocked the boat and pushed, anything to push the boat into deeper water. Finally, Kevin started the motor and winched in the rear anchor while I rocked the bow. Finally, the bow sprang free, leaving me onshore. Oops. The wind prevented Kevin from motoring close enough to shore. Another Kevin from our group heard the commotion and brought a rope. Finally I reboarded, and we anchored in deeper water. Now that was a first.

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Sunday morning was grim. No spring breakers on that cold dreary day. The wind was up again, and we were cold and tired. There would be no sailing or paddling for us. We towed the board and motored back to Burnt Store Marina.

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Monday morning, we took the boat out, staging the boat alongside a barge, a very strange first. Doug Buuck of All Marine Canvas brought our car and trailer to us, and we later visited him at All Marine Canvas. Doug had helped us out several times over the week. Meeting him was hands down our best “first.”

Each “first” challenged us develop new skills with wind and anchoring, among others, and the cold front reminded us not to get lulled by the idea of spring. The conditions pushed our abilities to communicate and work as a paddle-sail team even when separated by miles. I’m grateful to have these experiences as I work towards the Everglades Challenge 2022 and more SUP and sail trips with Kevin. And we’re both glad—after this year of Covid, that we have reconnected with WCTSS.