A Season in the Logbook

The Dock Goes Quiet

Our season on Lake Michigan has come to a close. The marina is emptying out, and Red Sky will soon be tucked in for the winter. But before we trade our deck shoes for slippers, I want to take a moment to reflect on what this season has meant, what we learned, how we grew, and how it all fits into the bigger picture.

kent and becca at the helm, the boat is heeling, the skyline in the background.

Season Highlights — 2025 at a Glance

Each of these moments added another line to our Logbook, stories of failures and successes, of learning and laughter, and a touch of quiet pride.

The Big Picture

Looking at our Sail Plan, this year fits squarely into the Experience and Proficiency chapter. Each sail, each mistake, each small victory. They’re all part of building the seamanship we’ll need when the horizon gets wider. Competence, and confidence, comes from repetition, reflection, and the courage to keep trying, even when the wind picks up or the docking gets dicey. And this season has taught us well.

Becca standing in the cockpit holding up the large, red, mylar balloon that she fished out of the water.

Looking Ahead

Exciting Announcement: We’re heading to Grenada in January!

Last year’s trip to the BVI was about easing into sailing. Those calm Caribbean trades were the perfect classroom (with room for guests!). But this time, we’re stepping it up: just the two of us, on a monohull, ready for new challenges and new waters. (The sailing may be a little more challenging, therefore, we have decided not to invite guests.) This will be another proof-of-concept.

And in other news: Red Sky is going out of service.

We won’t be sailing her next year, but we’re already cooking up exciting plans for what comes next. Stay tuned; the story just changed tack!

In Closing — Gratitude & Growth

Our Sail Plan is a living map, and our dream is unfolding one log entry at a time. We’re ending the season with more skill, more stories, and a deeper appreciation for the water.

Red Sky, rest well. Thank you for carrying us safely through another season; it has been an honor and a joy to sail on your decks.

From a sailboat on Lake Michigan, the Chicago skyline on the horizon.

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