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.

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.

Embracing, Then Abandoning, Old-Fashioned Navigation Methods

A beautiful sunrise over a marina, with ducks floating in the water that reflects the light

Kent shares his meticulous planning for our first Lake Michigan crossing. Despite detailed map plotting and weather monitoring, unexpected calm winds disrupted our journey! Forced to adapt, we resorted to using the "iron sail" on the first leg of or trip. This experience serves as a humbling reminder of nature's unpredictability and the need to remain adaptable while sailing.