Shakedown Cruise: Crossing Lake Michigan – Part 1

Memorial Day weekend was our first actual sail on Our Lady, our new-to-us Jeanneau 419 out of Waukegan. We’d had an orientation the week before but heavy weather kept us in the slip that day. So Monday, May 25th, was our first sail. Forty-one feet of boat we’d toured, but never taken anywhere.

Note: We had stew crew! My sister Maria came with us, which turned out to be one of our better decisions.

The marina at Waukegan has a different vibe than Burnham Harbor. It’s quieter, much less traffic. We’ve been based out of Burnham for three seasons and while it’s chaotic getting in and out of there, looking out at the Chicago skyline on the edge of the water is always a showstopper. It never gets old.

Day One: Waukegan to Navy Pier

Waukegan is our new home base, and we spent a few minutes getting the boat ready for take off, including mounting our new Starlink. We wanted to make sure we had reliable internet out on the open water.

We pushed off at noon with Kent at the helm for the first time on Our Lady. I stationed myself at the bow to watch our slip neighbor. Kent managed the exit perfectly, though I miscalculated the distance for our own bowsprit, which grazed a pylon on the way out. Okay. Small ignominy. We noted it and moved on.

The plan was a short jaunt to Navy Pier before jumping into a passage across the lake to New Buffalo. Wind was light outside the harbor and we raised the sails briefly, but with nightfall to consider, we pointed south and motored. Wind eventually came up near Chicago but it was on the nose. We arrived at Navy Pier around 7:30. We docked with help from the dock hands and the Ferris wheel lit up directly overhead.

We celebrated with dinner at Reunion right around the corner from the pier. Maria’s reflection on the experience: “That was the easiest I’ve ever gotten into Chicago.” And to that, we ordered drinks. Maria ordered sangria, Kent ordered a Blue Frozen Margarita, and I ordered an Aperol Spritz (with the understanding that I’d swap with Kent if I didn’t like it). I liked it. No swapping occurred. A new era has begun. (Scroll down for a 4 x 6 printable recipe card!)

We spent the night at Navy Pier with the city lit up around us and left the next morning. With Waukegan behind us, we felt ready to take Our Lady across the lake. More to come.

Kent and Becca are a Gen X couple from central Iowa learning to sail on Lake Michigan with SailTime Chicago. Sail & Savor is their logbook: the skills, the snacks, and the slow accumulation of good days on the water.

Printable recipe card: For the best results, print on heavy cardstock and make sure your printer settings are set to “Actual Size” (100%).