Milwaukee → Winthrop Harbor
September 28, 2026
Distance: ~34 nautical miles
Waterway / State: Lake Michigan — Wisconsin → Illinois
Locks: 0 | 0 total so far
Notable: Calm enough to run almost directly to our waypoints, with only a slight beam roll.
The Trip
We spent the morning seeing a little more of Milwaukee before heading south.
We took an Uber to the Milwaukee Public Market, walked through downtown and along the RiverWalk, and made our way back to a spot where we had taken a picture during the AGLCA Looper Lifestyle Seminar. This time we recreated the photo knowing that instead of just talking about doing the Great Loop, we were actually in the middle of it.
Once we got back to the marina, there were still a few boat things to finish. Greg finished staining the trim for the shelving area in the laundry room, Julie got the boat ready to leave, and Greg did the usual engine-room check before we pulled away.
The water was about as good as it gets. The waves were hitting us mostly on the beam, so there was a little rolling, but nothing significant, and we were able to run pretty much directly toward our waypoints. After some of the earlier Lake Michigan legs, that was a very welcome change.
Our destination was Winthrop Harbor, which is actually a good distance north of Waukegan even though we had been thinking of the stop as Waukegan.
The Experience
The marina itself gave us a reminder that not every stop is going to be picturesque.
Our slip had a pretty nasty dock and power pedestal. There was goose poop everywhere, along with green moss that we kept tracking on and off the boat. We sprayed the dock down, but there was only so much we could do with it. Greg ended up giving Breaking Awave a full wash before we left the next morning.
Fortunately, the evening itself was much better.
Julie’s cousin Dan and his wife Tina came to pick us up. We showed them around Breaking Awave, and then they took us out for dinner. It was nice to spend the evening with family after another day of moving south, and we even had some leftovers to take back for lunch the next day.
At the Helm
There wasn’t a major boating lesson on this leg, and that was fine with us.
The lake was calm enough that we could simply point Breaking Awave toward our waypoints and make steady progress south. After several days where weather and wave direction had played a much bigger role in the route, it was nice to have a day where the boat could just go where we wanted her to go.
The more practical reminder came at the marina: not all marinas—or docks—are created equal.
Sometimes the lesson of the day is less about navigation and more about remembering to keep the washdown hose handy.
Today’s Route
[Nebo route visual]
Today in Pictures
[Milwaukee Public Market, RiverWalk, recreated AGLCA photo, final boat projects at McKinley Marina, Lake Michigan underway, Winthrop Harbor arrival, family visit with Dan and Tina]