Casting Off
I feel so good about this sailing season, really proud. We’ve learned so much, grown more confident, and weathered the things that Lake Michigan threw at us, from choppy waves to the occasional small craft advisory. After a season so rewarding, I really wanted calm water and good weather for our final outing, an easy, low-stress sail to close things out. And the forecast looked perfect! Still, I couldn’t shake the feeling that maybe our luck had run its course. In a low-grade superstitious fog, I hesitated to make any plans or invite guests, even though having people aboard brings us great joy.
So when a friend from work posted on Facebook asking for fun things to do in Chicago, I took it as a nudge to snap out of it. The weather looked beautiful; there was no reason to hold back. Without even consulting the skipper, I told her we’d be sailing there on the weekend and I invited her and her 11-year-old son to join us.
To my surprise, the next day she texted: We’d love to come!
“Navy Pier Marina, This is Sailing Vessel Red Sky…”
It had been a long week and Kent and I were too tired to leave the night before. So we threw together a hasty plan: Let’s leave no later than 7:00 a.m., make a quick stop to stock up on snacks, and hopefully pull into the harbor by 10:30. Optimistic, as it turned out, we didn’t actually leave until 7:30 a.m. and arrived closer to 11:30.
By 11:45, we were on the water, heading north toward Navy Pier to meet Sarah and her son. Pulling into Navy Pier felt surreal — sailing right up to one of Chicago’s most iconic landmarks.
Kent had made a reservation ahead of time, so when he radioed the marina on our approach, his voice was calm and professional:
“Navy Pier Marina, Navy Pier Marina, Navy Pier Marina, this is sailing vessel Red Sky. We’re coming in to dock. Please advise.”
The reply came through the static: slip 14E.
Hearing that exchange — the clipped rhythm of marine radio — was such a small but thrilling milestone. My ear isn’t yet tuned to the fuzzy, formal chatter, but it made everything feel wonderfully official.
Meeting at the Dock
We spotted the red buoy marking the entrance and eased our way in. When we looked up, there they were, Sarah and her son waving from the dock. It felt like a movie moment.
The new Navy Pier Marina is beautifully designed for transient boaters — wide, angled slips and tall pilings. Kent guided us in smoothly, and a dockhand was waiting to grab the line I tossed.
A Perfect Day on the Water
And what a perfect day it was. The sky was blue, the breeze was light, and it was just warm enough to make the lake air feel soft. We headed back out onto Lake Michigan, careful not to venture too far in case our guests felt seasick.
Out on the open water, we turned off the engine and raised the sails. Everything went quiet, just wind, water, and sunlight. I felt so deeply lucky to be there, with Kent, and our friends. This is what makes our sails on Lake Michigan so special, the calm slows your breathing and stops the clock for a while.
Memories and Mylar
We sailed for about three hours, talking, laughing, soaking it all in. At one point, we spotted something shiny bobbing in the waves — another big Mylar balloon, just like the one we rescued earlier in the season.
We approached and I fished it out of the lake with the boat hook. It was a giant gold letter I, presumably for Iowa. (That hit a little close to home 😣.)
When the wind died completely, we lowered the swim platform and dipped our feet into the chilly water. The boy was the only one brave enough to keep his toes in for more than a minute!
Pizza, Pier Lights, and the Long Ride Home
Eventually the wind returned, and we sailed a bit more before turning back toward Navy Pier. Around 4:00, Kent called the marina again, and this time they assigned us slip 13, right by the marina office. We dropped off our guests, waved goodbye, and took a moment to appreciate how smoothly the day had gone.
By then, we were hungry. We wandered Navy Pier in search of food, first to the east (wrong direction, as it turned out), then all the way around before giving up and heading back to Burnham Harbor.
Pizza delivery to the boat felt like the right ending to the day. (Lou Malnati’s gluten-free pizza, we can’t quit you.) In the harbor, we sat in the cockpit eating pizza as the sun set, the golden light catching the masts.
We didn’t pull into our driveway until after 11 p.m., sun-tired and completely happy. It was the perfect finale to the 2025 sailing season.
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