Sailing Changed the Way We Do Summer

Kent and Becca sitting in the cockpit, smiling, with the lake and chicago in the background.

Our summers used to mean road trips, trout streams, and backyard weekends. Now, every other weekend, we grab our go-basket, hop in the car, and head for Lake Michigan. Sailing has brought a new rhythm to our lives — one that’s part adventure, part ritual, and totally worth the laundry piling up.

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.