Unintentional Learning, Yearning

“If you told me I could come along, I’d be here in a second,” my friend John says after a few inspiring hours on board Winnie. “Well, you can have the port bunk, ya know.” Instantly I see the wheels start turning, visions of dreams coming true sooner than believed come to his mind, giddy laughter. Everything could work out if he wants it to. A job is soon ending, the season for hiking the Pacific Crest Trail is upon us (a 2,700 mile long trail stretching the entire west coast). He wants to follow his gut.

John makes the hour drive home and already starts separating a keep and discard pile; organizing possessions based on importance and long-term value. “In four weeks we’ll be in Cancun, you can find a way across Mexico to start the trail,” I coaxed. In the small interior of Winnie, not even tall enough for John, at 6’3″ to stand up save for his head peaking out of the companionway hatch, proud dreams make one stand even taller. Onboard, dreams are more attainable and the wondrous world is more accessible.

The next morning, February 26, Kyle, Kassie, and I finished tying everything down on deck, preparing to embark on our first ocean passage of the trip: 270 miles from Panama City to Tampa, Florida. Extraordinarily small compared to projected passages in the Pacific, but this would be our shakedown sail. With this, we could see how Winnie sails with our Monitor wind vane, if everything is lashed down adequately, and whether our bodies are up to the task. Three days, two nights of continuous sailing while out of sight of land. Good strong wind in the forecast.

We followed a high pressure system that had produced 35 knot winds late in the night before. In its wake would be a consistent 20 knots. A bit strong, but Winnie is built strong. Leaving the shores of Panama City Beach, the sea moved, confused from current coming from the south, wind coming from the west, and us going southeast. The swell lifted us gently six feet up and down, but then a breaking wave would hit us from the side, rolling Winnie. Seasickness came on like a sneaky suspicion.

Farther out at sea, the seas only got bigger and with it the landlubbers’ wooziness. This was an unknown, I hoped my body could keep up. Sleeping in the bow of our ski boat as a child had prepared me for this motion. Exhausted, I was the lucky one to find minutes of sleep. For Kyle, beginning the trek with his head down in the electrical box and poor sleep the night before proved costly, taking the next two days to overcome the nausea. At sea, once you’re behind on sleep, hydration, or calories, catching up is that much harder. Kassie’s stomach turned to knots feeling the ocean swell for the first time. She spent the next three days trying to hold on, lying down in vain attempts to sleep. Every thirty seconds or less a much bigger wave would jolt us awake, rolling the boat to 45 degrees for a few agonizing seconds. Unable to sleep, eat, or move, she closed her eyes and waited for landfall.

The shakedown sail is a huge learning opportunity. Unable to reef the sail, we were overpowered and sailing her harder than necessary. We kept at 7 knots for days with the wind hitting our side, twelve foot waves breaking on deck, swamping the man on watch in the unfriendly night. We tested our foul weather gear, our sails, the wind vane, our bodies. We sailed south for too long in the night, not wanting to tack into the wind during the dark and sail blindly into the waves. Our third day was a bit of backtracking, but so it goes with sailing. At the mercy of the wind, unable to make a bee line for Tampa Bay, our engine helped us in the last hours to the bay.

The offshore cruising world is incredibly small, especially among young sailors. We tied to a pier, I snapped a picture for Instagram and later that night I get a message from fellow inspired sailor, Emily Richmond (bobbieroundstheworld.com). The pier we happened upon was her local hangout growing up, she congratulated us on our crossing. She’s now halfway around the world, 5 years in on her projected 5 year circumnavigation. We are constantly pushed into the naturally slow pace of sailing, delaying already vague deadlines. These days before continuing south are now intentionally slow. Florida has been about 70 degrees for the first time in months and we’re enjoying our leisure time.

In Gulfport (Tampa area), we were greeted by another friend with fresh salad and cold beers. A drive to the local taco shop traded for a dinghy ride to our beautiful sailboat. Far from home, we are able to connect with much cared for friends, all entering the throes of adulthood.

John won’t be joining us, but he’s now getting a passport and is putting his big dreams into action, already living a fun-filled life moving around the country from job to job. He’s hoping to meet us somewhere else along the way, with more than a few days notice.

Our journey is already becoming bigger than us and we’re grateful to all the people rooting us on and living vicariously through our unique opportunity. On our transom reads “Lake Lotawana, MO,” the port of call for Kyle and me, a landlocked state with veins to the ocean. To many, it’s inspiring and eye opening that we could sail from there to here, but to us it’s very matter of fact and practical. Even though this trip is not meant to raise awareness or intentionally inspire, we take the energy of our inspirations with us, gathered from others’ great feats. We pass this around and hope it tears down some perceived boundaries in getting where you want.



  1. I know there isn’t a day goes by where Ash and I aren’t dreaming about joining!

    Winnie is an inspiration to all of us. Keep living slowly.



  2. Good to hear you are enjoying some warm weather as you recover from a rough crossing! Thank you for the interesting report…..sail on!



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