Crossings: Lakes and Thresholds

Red Sky on the dock in New Buffalo, sun setting in the background.

Winds up to 22 knots, a reef that wasn’t there, and the quiet thrill of doing something you once thought was too much — our second crossing of Lake Michigan was equal parts challenge and growth. This is the story of how our comfort zone expanded, one gust at a time.

A Sister, a Regatta, and the Sea 

Kent and Becca sitting behind the wheels of a double-helm sailboat.

We planned for a quiet overnight on the boat — just us, the marina, and an early start the next morning. What we got instead was a noisy festival, a last-minute hotel room, a flamenco dancer, and one of the best sails of the season. My sister joined us for her first-ever monohull sail , and I was at the helm to bring us back in — this time with spectators watching from our neighboring slip! (No pressure, right?) Spoiler: I nailed it. But not without a few nerves.

Second Time’s the Charm: A Smooth Sail and My Redemption at the Helm

the sunlight glimmering on the water in Lake Michigan, buildings on the horizon.

After a rough first landing on our season opener, I was more than ready for a second shot. This time, everything clicked — calm winds, smooth sailing, and determination at the helm. I learned that docking isn’t about power; it’s about patience, timing, and a few well-placed nudges. And just like that, I found my redemption… and a rhythm I can’t wait to keep building on.