Days 158-162 Milwaukee to Kenosha to Chicago to Joliet, IL

Tuesday September 24-Saturday September 28, 2026

TUESDAY

Today, Trisha (Jeff’s Sister) arrived in Milwaukee! She’ll be staying with us until Sunday before heading out from Joliet, IL. Once she got settled in, we had some lunch on the back deck and spent the afternoon catching up.

Later, we headed out for a pre-dinner cocktail at the Safe House, a truly unforgettable spot tucked behind a red door in an alley near the Milwaukee River. Since 1966, this hidden gem has been delighting guests with its top-secret vibes. You need a password to get in (which adds to the fun), and from there, you’re led through a series of secret doors into a world of espionage.

Inside, the atmosphere is electric—decked out in authentic spy gear, James Bond memorabilia, and clever surprises around every corner. We only stopped in for a drink, but the cocktails were unique and delicious. They seated us in a cozy private booth at the top of a set of stairs. Just before we left, our waitress asked if we wanted to see something cool. Naturally, we said yes. She closed the doors to our booth, pushed a hidden button—and suddenly, the whole booth turned 180 degrees! It was like something straight out of a movie.

From there, we walked over to Mader’s, a classic German restaurant that’s been in business since 1902. The ambiance was old-world charming, and the food absolutely lived up to the hype. We shared a variety of delicious dishes and left feeling very satisfied—and very full.

A truly fine evening to kick off the week with Trisha!

More pics from our walk:

WEDNESDAY

Milwaukee River Adventure – A Dinghy Tale

The winds and swell on the lake kept us from going anywhere today, so we opted for a little exploration closer to home. We took the dinghy up the Milwaukee River — such a great way to take in the downtown skyline. The mix of modern and historic architecture from the water is truly something else.

After soaking in the sights, we turned around and headed up the Kinnickinnic River in search of a spot called Barnacle Buds. A guy we met at the dock a few days ago recommended it — we call him “Drunk Gary.” Nice guy, but, well… the name says it all. 😄

We managed to find the place, but docking turned out to be a challenge. Despite plenty of docks and slips (most of them empty), signs everywhere screamed NO DOCKING. Apparently, all the dockage is privately owned, and they don’t allow tie-ups for the restaurant. There was a wall a little ways back we could have used — if it weren’t so high it would’ve required climbing gear.

In the end, we took a chance, pulled up, tied off briefly, and went for it. Worth it! The place had great fresh fish and chips, plus a full menu. A very fun, laid-back spot.

The ride back, though… that’s where things got spicy.

We knew we’d be heading into the wind once we left the river and hit the harbor — but what we didn’t plan for was running out of gas. Yep. Turns out 1/3 of a gallon doesn’t take you as far as you’d hope. Pro tip: bring the spare can. 🙃

Luckily, we sputtered out right by a small community park with a dock. Perfect timing. We tied up, and Jeff hoofed it to a gas station about half a mile away. He came back not just with gas, but with a brand-new spare can. Legend.

Back on the water, we hit some pretty decent chop even in the protected harbor. Let’s just say a few of us got more wet than others — and we laughed about it all the way back. We told Trisha we wanted her visit to be memorable. Mission accomplished!

THURSDAY

Into the Big Wide Open!

We started our morning with coffee, showers, and French toast — a relaxing start while we waited for the waves and swells to continue dying down. Timing our departure was key. Around 10 a.m., we headed out for Kenosha, just over 30 miles away.

The waves were still a bit bigger than we’d have liked, but fortunately they were coming from behind. To get on course, we had to head out a bit before turning south, which put the waves on our beam for a while — never anyone’s favorite. Still, we made it to Kenosha with just enough time to visit the Civil War Museum. As most of you know, Jeff loves museums like that, so it was a great stop!

Later, we enjoyed docktails aboard our boat with fellow Loopers from Double Trouble III. Trisha got a great introduction to the kinds of conversations Loopers share when they get together. Fun was had by all!

FRIDAY

From tiny Franks Diner to Big Downtown Chicago!

We were up early to enjoy breakfast at Franks Diner, the oldest continually owned diner in the United States. They serve up hearty breakfasts, classic lunches — and a little bit of sass. Most people love the atmosphere, though a few might get offended. Either way, it’s a fun place with great food!

The diner’s story began in 1926, when Anthony Franks read a newspaper article about lunch car-style diners and decided to order one. Franks Diner was built by the Jerry O’Mahony Company, one of America’s original diner manufacturers based in Bayonne, New Jersey. After a short ride by rail — followed by a long haul pulled by six horses — the lunch car rolled into downtown Kenosha, Wisconsin.

Interestingly, the city delayed its opening for a year, claiming there were already too many Greek-owned restaurants at the time.

September of next year they will celebrate 100 years of being in service!

Cruising into Chicago: Calm Seas, City Lights & A Side of Chaos

We left the marina behind and set out on our journey to Chicago under clear skies and a gentle breeze. The water was calm, the sun was warm, and the day couldn’t have been more perfect for a cruise. After a smooth 5+ hour ride, we pulled into DuSable Harbor Marina right around 3 PM — the skyline rising ahead of us like something out of a postcard.

To kick off an early celebration for Jeff’s upcoming birthday (just over a week away!), we headed out for dinner. The unanimous choice? Giordano’s, of course! We shared a plate of bruschetta and dove into a classic deep-dish pizza — gooey, cheesy, absolutely decadent. Every bite was better than the last.

Back at the boat, we wrapped up the evening on a high note. The city lights shimmered around us as we lounged out back, sipping espresso martinis and soaking in the view.

It was one of those moments where everything just clicks — peaceful, happy, and content.

…Until it wasn’t.

Just as we were drifting off to sleep, we were jolted awake by what sounded like a full-blown concert — inside our boat. Turns out the neighbors had returned from a joyride and decided to keep the party going… loudly. The music was blaring so hard, we could barely hear ourselves think. We peeked out to see 3 or 4 guys on the boat, and the poor captain was shouting instructions on how to tie up — not that anyone could hear him over the pounding bass.

I finally had enough, popped up through the hatch, and yelled at them to turn it down. To their credit, they did — and even managed a slurred apology. But wow… stupid drunk people.

Still, despite the late-night antics, it was an unforgettable day. Beautiful weather, amazing food, city views, and a boatload of memories — loud neighbors and all.

SATURDAY

A Day on the River: From Chicago’s Buzz to Joliet’s Embrace

Today was the day Trisha had been waiting for — and it couldn’t have been more beautiful. The sun was shining, the air was warm, and the city of Chicago was alive with the vibrant energy of early fall. We had a bit of a slow start, needing to wait until around noon to begin our journey down the Chicago River. A rowing regatta had temporarily closed off a section, so we relaxed and soaked in the anticipation.

Once we were finally cleared to go, we found ourselves in the heart of the action. The river was buzzing — tour boats gliding past, café patios packed with people, laughter echoing off the buildings, and cameras flashing from every angle. It felt like we had front-row seats to the city’s own little celebration of autumn. Trisha was grinning from ear to ear.

But like all good things, the downtown magic eventually faded behind us. As we made our way further south, the scenery shifted dramatically — trading in glass towers and riverwalks for steel, smokestacks, and gritty industrial zones. The pace slowed, the waterway thickened with working traffic, and the glamour of the city gave way to the muscle of the river.

We hit a significant delay waiting for a tow and his string of barges so we could share a lock. It took a while — longer than we would’ve liked — but that’s part of the rhythm of river travel: hurry up and wait.

By the time we reached the Joliet wall, the sun had dipped below the horizon. It was much later than our usual arrival window, and we were tired and ready to tie up. But what a welcome we received! Three fellow Looper boats (Jelly Bean, Avontuure and the 3rd one hadn’t been named yet) were already there, ready to catch lines, big smiles, and happy greetings — the kind of camaraderie that makes this journey so special.

Dinner was a late one aboard the boat, nothing fancy, but the kind of meal that hits just right after a long day. Tired, full, and grateful, we ended the night reflecting on a day filled with contrasts — the energy of the city, the stillness of delays, and the quiet joy of being welcomed at the end.