Day Two: Navy Pier to New Buffalo

We pushed off of Navy Pier at 6:00 AM and pointed for New Buffalo, Michigan, about 60 miles across the lake, our third crossing of the lake and most aggressive to date.
We had been on Our Lady for approximately eighteen hours at this point. Despite my orientation with Ryan only one week ago, I couldn’t get the coffee maker to work nor the stove to light. These are not complicated things. They are, however, complicated things when you’re on a moving boat in the early morning and you haven’t had coffee yet because you can’t figure out the coffee maker.
We also had a lot of flies. They weren’t the biting kind, but they were committed. We managed to keep them out of the cabin but we did not manage to get rid of them.
Maria saved us. She came provisioned and when the time came, served us a lunch of tuna lettuce wraps and mango and grapes eaten in the cockpit on flat, glassy water. No wind that day either. We motored the whole crossing.

We pulled into New Buffalo around 2:30 PM. This is the same marina where we ran aground last year (read about that particular adventure) and sure enough, there she was, the Miss Jamie Lynn, the dredge barge, apparently a permanent fixture. I brought us into the slip, my first time at the helm on Our Lady. I got us a little crosswise in the slip, but there were no neighbors and we corrected quickly.
That evening, Kent’s mom and sister + family, who live in western Michigan, met us for dinner at the Stray Dog. I opened birthday presents. A lovely way to spend the night before turning another year older.
Notably, we’d watched the weather forecast all day. Thursday was building into something ugly – a small craft advisory, heavy winds, and nine-foot waves. Our original plan had us stopping at Navy Pier on the way back, adding another night, another day. We made the call: skip it. We’d head straight back to Waukegan on Wednesday, get home with time to spare, and build in a buffer in case anything slowed us down.
This is one of those things sailing teaches you well: the plan you made on shore is a suggestion. The weather is the actual plan. The sooner you get comfortable changing your itinerary, the better sailor you become.
Kent placed a Walmart order earlier in the day: a broom, a hose + nozzle, and a small coffee maker, to be delivered to the New Buffalo Marina. Upon delivery, we discovered that the broom wasn’t available and the hose was too short. The coffee maker, however, was immediately promoted to essential equipment.
Before bed, Maria and I borrowed a bucket from the marina and scrubbed the deck by hand to clear out the fly situation. It worked well enough.
Day Three: New Buffalo to Waukegan (My Birthday)
Wednesday morning, a day earlier than planned, we pushed of at 5:45 AM. I was at the helm backing out of the slip and a fender got snagged on a pylon and swung the bow about 90 degrees. There were no other boats, no consequences, just that particular “I’m a dipshit” feeling of wishing you could do the simple thing simply. I turned the rudder, moved the throttle to forward, and got us underway.
Out past the breakwater, Lake Michigan handed us a gorgeous sunrise. I considered it a gift from Kent, not because he arranged it, but because we were there to see it. What a beautiful birthday present.

We set out at a heading of 315 degrees and ran at full throttle. The water stayed flat. The new coffee maker worked perfectly. Our new Starlink worked perfectly for live tracking, weather monitoring, and the general comfort of knowing it was there if we needed it. We fell into two-hour helm shifts, which felt prudent for a crossing of this length even if the conditions were calm. Somewhere in the middle of the lake we passed the freighter M/V James R. Barker. We also passed more mylar balloons than we’ve ever seen on the water, dozens of them. It never stops being sad.

The best moment of the return trip: We lit the stove! We’d been at it for two days. Maria lit it, announced it, and made eggs for breakfast and Korean beef for lunch. We ate like it was a celebration, because dammit, it was. (Never did figure out what was the problem!)
We spotted the Waukegan stacks from offshore around noon. Made it to the marina at 2:30.
And here is where I will tell you about the slip fiasco.
The Slip Fiasco
Kent brought us in beautifully. Our Lady is 41 feet long and pulling a 41-foot boat into a slip while someone makes hand gestures from the bow is a genuine coordination exercise, and he did it gracefully. We all exhaled.
But whoops! Wrong slip.
We dropped Maria on the dock. Kent and I would reposition. Simple enough.
It was not simple and I’m not going to reconstruct what followed because some things are better left un-documented. What I will say is that after attempts were made, Kent got the bow close enough to the dock that I could toss Maria a line, and Maria — who’d fed us for three days across Lake Michigan— grabbed that line and physically dragged our asses in. We tied off and exhaled, again.
In the end, there was only one casualty. In the chaos of departure, just as I stepped off the boat to walk back to the car, I dropped Kent’s Kindle into Lake Michigan.
It’s at the bottom of Waukegan Harbor now. We know this.
Lessons Learned
Four seasons in, and this trip handed us a curriculum. Here’s where we landed:
- Orientation is essential, but it isn’t mastery. We’d toured Our Lady and talked through her systems. That is not the same as knowing a boat. The difference shows up at 6:00 AM when the coffee maker doesn’t work.
- Crew matters! Maria held it together at several key moments. Good crew is a good thing.
- Give yourself margin. Two-hour helm shifts on a flat, calm day crossing might have been overkill. It also meant we arrived at the marina alert and not frantic, with time to make our docking mistakes in relative peace.
- You may dock in the wrong slip. Possibly more than once. Having someone on the dock to catch your line is worth everything.
We’re back in Iowa now. The flies are gone. The Kindle is gone. The stove works. We had our coffee.
Hello Our Lady. It was nice to meet you.
Want to read about our previous sail into Navy Pier?
Discover more from SAIL & SAVOR BLOG
Subscribe to get the latest posts sent to your email.

