South Haven, MI > St. Joe, MI > Chicago, IL > Hammond, IN > South Side of Chicago
Following a one night stop in South Haven, we set off early for St. Joe – a manageable 24-mile cruise. Like the day before, the first half was relatively calm. Then, true to Lake Michigan’s fickle mood, the waves shifted direction, kicked up, and we found ourselves rolling and see-sawing through an increasingly restless lake.
South Haven, MI to South Side of Chicago, IL
The sky started with a peachy – poofy glow, soft and picturesque, but quickly darkened to stormy gray. Then came the rain. Then bigger waves. Fortunately, we didn’t have far to go.
Lake Michigan clouds
As we approached the breakwater and entered the St. Joe River, Captain Dave powered up the Cummins, navigating us into the chute with just enough muscle to make the turn. Waves crashed from side to side, giving us a Cedar Point-level ride until we reached the calmer river waters. A sharp left before the railroad bridge brought us into West Basin Marina – our safe harbor.
St. Joe River
Upon checking in, we learned we’d arrived just before the Tri-State Regatta would roll in – with more than 100 sailboats heading to both our marina and the adjacent yacht club. “It might get a little crazy,” they warned. We smiled and the captain replied, “We might be old, but we’re not dead!”
Tucked into the north shore of the St. Joe River, we had easy access to the yacht club, the north beach, and the peaceful, park-like marina grounds. Getting across the river to Silver Beach and downtown was a bit of a trick, but we made it daily on our bikes. The ride itself – up over an underpass along a highway bridge, alongside railroad tracks, and along the river and lakefront – offered stunning views and plenty of things to do.
We hit up the local eateries, watering holes, shops, farmer’s market, parks, and of course, the beach. Dave was in heaven – a train track ran right by the marina, crossing the river via swing bridge. Each whistle, bridge swing, and passing engine brought him pure joy.
St. Joe Trains
One afternoon, we climbed the St. Joe Lighthouse. The final 20 steps were a near-vertical ladder, but the view of Lake Michigan at the top? Absolutely worth it.
St. Joe Lighthouse
For a brief moment, it felt like the calm before the storm. The marina was peaceful… until well past midnight when the regatta boats began arriving. The night before, we’d ridden our bikes to the beach to watch the wind whip up waves – Lake Michigan putting on a full show, crashing and spraying up over the break wall. The pier was barely passable, but we ventured out about a third of the way. Amidst the golden hour light, spray, and wild waves, we even witnessed a marriage proposal. A chaotic kind of magic.
St. Joe Pier – Proposal
The waves finally calmed by the time the boats made their crossing. What’s normally a 9-hour sail for the fastest racers stretched to 12. We expected a 2 a.m. circus, but the first boats arrived quietly around 4:30, most pulling in by 6.
Tri-state Regatta
The regatta crowd? Surprisingly chill. After some early-morning celebrations, most passed out in hammocks, tents, and on deck. By afternoon, the yacht club came alive with awards, music, and dancing – a lively but not-too-rowdy celebration. We turned in early, but the distant music was just right to lull us to sleep.
Goodbye Michigan, Hello Chicago
The next morning, we set out – and so did the regatta boats, heading south to Michigan City. We’d considered joining them to take advantage of Michigan’s low diesel prices before entering high-tax Illinois (especially when you’re carrying 500 gallons), but the weather was just too perfect to pass up.
Instead, we made the full 60-mile run across the lake to Chicago.
Chicago – 20 miles out
We wrapped up our 17th state on the journey – and the final of all five Great Lakes. Born Buckeyes, we weren’t supposed to fall for Michigan… but we did. The stunning shorelines, blue-green waters, charming coastal towns, and welcoming harbors were unforgettable.
Chicago!
We caught our first glimpse of the Chicago skyline 20 miles out. True to our impeccable timing – we’d hit New York City on Memorial Day weekend last year, and now Chicago on Labor Day – the city was buzzing. Boats everywhere, heading to the “Playpen,” while we carefully motored into the brand-new Navy Pier marina, built just for transient boaters. It was a Looper’s dream: unbeatable views and easy access to the heart of town.
After weeks of solitude in Canada and peaceful days on Lake Michigan, the buzz of downtown Chicago was a full-on culture shock. The Riverwalk was packed, the river itself a chaotic mess of tour boats, pleasure crafts, wave runners, and kayaks – we were glad we weren’t navigating it ourselves.
Chicago River Walk
We biked north and south along the lakefront on an 18 mile paved trail, sampling Irish, Italian, and Spanish fare in tucked-away city spots and a Chicago dog on the pier. And Tasha finally got her “couch therapy” session in – a cherished comfort session with Dr. Bob Hartley, our favorite TV psychologist.
Lakefront Trail and Couch Time Therapy
We met up with our son Nick for dinner and enjoyed Chicago’s twinkling skyline from our own deck. It had been 20 years since our last overnight in the city, and nothing beats staying on the water in the middle of it all.
Nick and the city just steps from Now or Never
After several days, we left Chicago early morning with surprisingly calm water, weaving out past boats still making their way in. Next stop: Hammond, Indiana, for fuel – our final leg of what we jokingly called our own Tri-State Regatta: St. Joe, MI, Chicago, IL, and Hammond, IN.
Goodbye Chicago!
With Lake Michigan readying to see some of its biggest waves of the season (measuring up to 17 feet on the east coast), we made the smart call to head inland via the Cal-Sag River. That meant skipping a night at the casino, but it also meant calmer seas.
Because of our height, we were a bit too tall to cruise the Chicago River (lowest fixed bridge is 17 ½ feet – a nail-biter for our boat). There’s no turning back once you start, and after seeing the river chaos, we were more than happy to keep Now or Never in one piece.
The Cal-Sag Canal may not be scenic, but it was steady – filled with barges and industrial zones. After passing through a lock, we pulled into a working boatyard on Chicago’s south side. Nothing fancy, just a dock – but it worked. It rained most of the day and night, and we were well-positioned for our next run to Joliet.
Sharing the rier on Chicago’s south side
It’s hard to believe summer is over, as we just wrapped up Labor Day weekend. We’ve left the Great Lakes behind, and now, we’re on the final leg of our Great Loop adventure – a journey years in the making and years on the water.
Cheers! David, Tasha,
& Remy forever in our hearts! – Loop Dog for 1 year and 3357 miles
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