The first drive to the harbor in May is its own small ceremony. We’ve been anticipating it all winter. It finally came. Last weekend we drove up to Waukegan, IL on a morning that looked like it was going to be a great day for sailing. Bright and breezy, the lake was visible as we came off the highway. Our plan was to meet our captain, Ryan, get out on the water, and learn our new boat.
Lake Michigan had other ideas, as she often does.

By the time we reached the harbor, the winds were steadily above 20 knots and Ryan mentioned there was a seiche. There’s a word I’d never heard before! He explained: it’s a Lake Michigan phenomenon caused by wind and atmospheric pressures where the lake essentially sloshes several inches of water from one end of itself to the other, like in a bathtub. It sounds almost gentle when you describe it, like a tide. But on the dock, watching the water move up and down several inches every 20 minutes or so, it was clear we weren’t going anywhere.
So we stayed and got oriented to the new-to-us boat.
Meet Our Lady
We’re in our fourth season with SailTime Chicago, a fractional membership sailing club that gives us access to a boat for the summer on Lake Michigan. Previous years we sailed on Red Sky and Sister Sail. This year, we’re on Our Lady, a 2019 Jeanneau 419 out of Waukegan, IL. She’s bigger, more boat in every direction. (To be clear, she is not our boat, we do not own a boat. But she’ll be ours for the summer.)
A nicely sized v-berth forward, two aft cabins, and two heads. (I’m already assigning bunks and we’ve not even cast off!) Ryan walked us through all the systems on board, the electronics, sails, safety gear, all of it, with the patience of someone who genuinely enjoys that part of his job. We didn’t move an inch off the dock but I think we might have learned more about the boat than if we’d had a breezy afternoon on the water where we’d have been too busy to absorb anything.
The wind and the seiche did us a favor, as it turned out!
One other thing worth noting: this season looks different from previous ones. Before, we had the boat a couple of times a month in shorter AM/PM slots, which was great, but the schlepping back and forth to Chicago was tough. This year, we’ve shifted to fewer but longer stretches on the boat. More time to settle in, more room to actually go somewhere. And since Our Lady has the berths for it, we’re making plans to have guests aboard! That alone changes the feeling of the season.
The Thing I Hadn’t Noticed About Burnham Harbor
Here’s something that caught me off guard: Waukegan is small and quiet.
Burnham Harbor, where we sailed from previous years, is right in the middle of Chicago, which means it is magnificent. But it also means that the moment you clear the breakwall, you are in a high traffic zone! Sailboats, powerboats, water taxis, tour boats, all of it moving north and south in a busy highway of chop and wake. It demands your attention from the first second you’re out and it demands patience as you have to get well beyond it before you can hoist the sails.


I get very nervous every time we set sail. I’ve noticed it but I hadn’t really examined it. I’m a fairly confident sailor, I trust our skills, we’ve put in the hours. But under those circumstances, the nervousness felt warranted to me! I didn’t question it! But it didn’t quite make sense to Kent and we’ve talked about it, often.
Looking out at a much quieter stretch of water from the dock in Waukegan, I think I figured it out. It’s not the sailing that makes me anxious. It’s the billions of dollars of sailcraft, the merge, the immediate, no-easing-in, full-speed-ahead nautical freeway that starts the moment you leave Burnham Harbor.
Waukegan doesn’t have that. And realizing this while standing on a boat that didn’t move out of its slip, it felt like a small but useful thing to know about myself.
What the Day Actually Was
So we didn’t get our check sail. We didn’t get to feel Our Lady move on the water or get any real read on how she handles. But that will come, we have a whole summer ahead.
What we got instead was a calm afternoon with a patient captain, a thorough walkthrough of a boat we’re going to spend a lot of time on, and an accidental insight into why sailing has felt more stressful than it probably needs to.
We’re not experts at this. We’re still very much in the part of the learning curve where some days the lesson comes from doing and some days it comes from just showing up and paying attention. This was a paying-attention day and it was perfect.
Our Lady is waiting. The season is just getting started.
Kent and Becca are a Gen X couple from Iowa learning to sail on Lake Michigan. Sail & Savor is their logbook — the skills, the snacks, and the slow accumulation of good days on the water.
Discover more from SAIL & SAVOR BLOG
Subscribe to get the latest posts sent to your email.

