We left the Joliet Wall early and spent the day working through three locks, learning a little more at each one.

By the time we reached Heritage Harbor in the rain, we had made good progress south, gotten more comfortable with floating bollards and lock procedures, and officially settled into river travel.

We left Navy Pier and almost immediately entered a very different kind of boating day: our first lock, the Chicago River through the skyscrapers, bridges, river traffic, barges and eventually our first night tied to a wall in Joliet.

It was one of the coolest stretches of the trip so far—and one that gave us several new things to learn before the day was over.

We left Winthrop Harbor in heavy fog, but as the morning went on the lake became almost perfectly calm and Chicago slowly began to appear through the haze.

By the time we reached Navy Pier, the fog had mostly burned off, the sun was out, and we were tied up beside the Ferris wheel with the Chicago skyline right in front of us.

We spent the morning enjoying a little more of Milwaukee before getting Breaking Awave ready to move south again.

The water was about as good as we could ask for, the run was easy, and we ended the day in Winthrop Harbor with family—although our new dock left a little to be desired.

After a week at home, we came back to Port Washington ready to pick up where we had left off.

Lake Michigan was much friendlier this time, and the three-hour run to Milwaukee was easy and calm. We came into the city right around sunset, which made for a pretty great return to the trip.

We left Sheboygan planning to make Milwaukee our next stop, but a later departure and the conditions on Lake Michigan made Port Washington the better choice.

It turned out to be a change of plans we were very happy about. We found a great little town to explore, while the weather made it increasingly clear that Breaking Awave wasn’t going anywhere for a few days.

After the rough crossing into Sturgeon Bay, the trip south to Sheboygan was much friendlier—but still gave us a few more lessons in balancing boating, work and the electronics aboard Breaking Awave.

By the end of the day, we were tied up in Sheboygan and walking to a great Italian dinner after another long day on Lake Michigan.

A neighboring boater in Northport summed up the weather situation pretty simply:

“Get your ass across the lake.”

So we did.

What started as a decision to get across Lake Michigan before the weather closed in turned into our longest and most demanding passage of the Loop so far—and then, thankfully, a much quieter day enjoying Sturgeon Bay.

By the time we returned to Traverse City from Escanaba on August 3, the Great Loop was no longer some distant plan. We had just over a month before departure, a boat that still needed a handful of projects completed, a house that needed to be handed over, jobs that weren’t going anywhere—and an increasingly impressive pile of things we somehow needed to fit aboard.

This was the final stretch.