Crossing Lake Michigan – an Epic Adventure: The Whole Story

Last week, I shared a short video on YouTube—a snippet of our Lake Michigan crossing (see below). It captured the breathtaking beauty of the lake, our exhilaration and sense of accomplishment. It was a beautiful trip, one to remember. And another first for us. 

I’ll be honest with you, the video glossed over a lot. (Such is the nature of sailing and video making, it is very difficult to do both at the same time.) So, here, I want to give you a detailed account of how our trip actually went.

The Whole Story

To recap, our three-day sailing adventure began at Burnham Harbor in Chicago. From there, we motored (mostly) to Michigan City, IN, and then New Buffalo, MI, where we enjoyed a day with family. Finally, we sailed all the way back to Chicago—glorious.

But our tale started on land, in St. Joseph, MI, during our annual two-day family reunion. After a sun-soaked day on the beach, and the festivities quieted down, we set our sights on Chicago. The drive—an hour and 45 minutes—hugs the southern shore of Lake Michigan, with Michigan City as the halfway point. I mention it because when we set sail out of Burnham Harbor, we headed directly back from whence we came!

Leg 1

At 11:00 am, we departed from the marina, our routine well-practiced. This time, Kent took the helm, a departure from my usual role. The wind was light, the sea was calm, and the sun was shining. Outside of the breakwater and well into Lake Michigan, we raised our sails. 

To the northeast of Burnham Harbor, the Four Mile Water Crib is a familiar waypoint. On a typical day sail, when we’ve gone past the crib, we know we’ve ventured quite far. To me, catching sight of the crib and sailing past it marked the beginning of our voyage.

As we set sail, the southern shore of Lake Michigan was easily visible: the southside of Chicago skyline and the LakeShore Coal Company (and Ameristar Casino) in East Chicago, IN. I think we could even make out the steel plant in Burns Harbor, IN. The small, dark, faint, silhouettes of the buildings and smokestacks gave me comfort because I knew that at some point, we were going to lose sight of Chicago, and that thought made me nervous.

Two hours into our passage, I took the helm, relieving Kent so he could take a quick decompression nap. Ahead on the horizon, I spied a freighter ship. It sat squarely in my path and I had to make several adjustments. I decided to tack, and I managed to pull it off single-handed. 

Emerging from the companionway, Kent surveyed the cardinal directions. His Spidey-direction-sense kicked in, and he asked, “Did we tack?” I was amazed at his intuition! He explained that he’d sensed the movement while lying down. 💀 Pointing ahead, I directed him to the freighter ship, which he identified as the SS Arthur M. Anderson, the same vessel that accompanied the SS Edmund Fitzgerald on the night it succumbed to Lake Superior in 1975. 

To reach Michigan City before nightfall, Kent calculated: we needed to maintain a speed of about 6 knots. But the winds blew directly from our destination, to make headway, we’d have to tack back and forth. No less, the wind was barely a whisper that day at 4 knots. We were averaging 3.5, so we made a pragmatic decision to deploy the “iron sail.” We fired up the engine and motored the rest of the way.

Throughout this leg of our journey, land remained in view. As we continued east and south, Michigan City appeared on the horizon. We arrived at around 8:00 in the evening.

The slip at the Michigan City Port Authority marina was well protected from the action of the lake water. And somewhere there was a live band belting out No Doubt covers—a serendipitous soundtrack to our arrival!

No Access, and the Kindness of Strangers

When we made reservations at the marina, they assured us an access card would be tucked inside the electric hookup box. But I searched high and low and there was no access card to be found. Meanwhile, Kent struck up a conversation with a couple who had just strolled through the gate. When he mentioned our access card problem, the gentleman nonchalantly pulled his own card out of his shirt pocket and slipped it into Kent’s hand. We objected and refused, without success. He insisted, it would be just fine if we used the card until the next morning, at which time we could toss it into the back of their boat.

And if that wasn’t enough, when we asked about ordering Uber Eats in this town, he nonchalantly pulled his car keys out of his shirt pocket and passed it over to Kent’s hand! This was a bridge too far. We thanked him profusely but declined. We were most grateful for their kindness, and if I could remember their names, I’d call them out. 

Back in the cabin, hungry and sunbleached, we ordered Five Guys for a late dinner. By 9:30 pm, we nestled into our berth and had a good night’s sleep in the still waters of the marina.

Leg 2

Morning arrived and we made coffee and enjoyed the sunrise. Thanks to kind strangers, we were able to freshen up in the marina facilities. Underway, our sails and the calm water carried us eastward to New Buffalo, three hours away. While it’s certainly not any kind of a failure to use the motor when one is sailing, it is most pleasing to use the sails. On this leg of the trip, we managed to sail the entire way!

Approaching the New Buffalo Municipal marina, we received a shore-side welcome—Kent’s mom, sister, and niece waved us in! We pulled into our reserved slip, tied off the lines, and within minutes, were gathered with family at the Stray Dog Bar & Grill.

Run Aground, and Unexpected Heroes

After lunch, we were eager to take our family on a sail, a first for our niece visiting from Texas! The five of us stepped aboard Red Sky, and after a quick safety briefing, we eased out of the marina. If you recall a previous post on hosting guests onboard, you’ll know that we take it very seriously…. Well, we were put to the test. We talk the talk, but do we walk the walk?

Just beyond the breakwater, our niece expressed some discomfort and so, out of an abundance of caution and concern, we did indeed turn back. 👍👍

This is where it gets fun….

Earlier that day, Kent had reviewed the U.S. Coast Guard’s “Notice to Mariners,” a weekly update on issues of safety around the lakes. It indicated that the center of the channel in the marina had a build-up of sediment. So to avoid running aground, he avoided the center of the channel. Consequently, we ran aground on the right side of the channel. 

In a flurry of action, I directed the ladies to the foredeck, hoping to shift our balance onboard. Meanwhile, Kent pulled out all the stops: maneuvers, bow thrusters—the works. But we remained stuck. And then, like a maritime miracle, a huge dredging barge—the Miss Jamie Lynn—entered the marina right behind us! Incredibly, when the crew saw we were stuck, they stopped to assist!

To prepare for our rescue, our guests moved back into the cockpit while I stayed on the foredeck. The barge anchored with a jack-up rig about 15 feet from our bow and a crew member prepared to toss us a line. At the bow, I wedged my right leg between a stanchion and the furled jib sail, and when the line came, I caught it with both hands! I swiftly tied the line off on the bow cleat and waited. Suddenly, the line snapped tight, then immediately went slack. At that moment, I put one more wrap around the cleat. When I looked up, I discovered I was being chastised by the experienced sailor, using strong hand motions, for handling the line when it might have been under pressure. He was absolutely right. I should not have handled the line. In fact, I probably should have stepped away. Had the line snapped tight again, or snapped in half, it could have easily caused serious injury. 

With the line secured on the bow cleat, the barge pulled us from the sludge within minutes. Back in our slip, we tied off, and secured the boat. We spent the rest of the day hanging out with our family, and returned to Red Sky that evening.

Leg 3

The following morning we would set out on the longest leg of our journey. To play it safe, we decided to push off as soon as we awoke. We could make coffee, get cleaned up, etc. while we were underway. That is exactly what we did. 

Perfect conditions—steady northern winds and calm seas—ushered us out of the marina. We hoisted our sails and rode the breeze, reaching speeds of around 6 knots. We were pleased and optimistic that we would make it back to Chicago before nightfall. ⛵️

The day unfolded slowly and beautifully. Coffee in hand, we reveled in the sights and sounds of sailing. I had planned for ample leisure—my tablet with a drawing app and stylus, and a handful of downloaded YouTube videos. But I could not keep from standing watch! I could not take my eyes off of the horizon.

Three hours in, no land in sight. 

Kent and I have been watching sailing videos for about 4 years; it is our nightly routine. Much of that content has taken place in the heart of the Atlantic Ocean. The thought of being out of sight of land…. I shudder when I think about it. Don’t you?

Truth be told, our sailing adventures often straddle the line between anxiety and exhilaration. Docking? Anxiety. Broaching? Downright scary. But sometimes, we’re ready. And that’s how it felt when we found ourselves surrounded by nothing but sea. Fear? Surprisingly absent. For five hours, we sailed beyond the horizon, out of sight of land and cell service (thank goodness for VHF radios!).

“Land ho!”

When suddenly the Chicago skyline shimmered through the haze on the horizon, it didn’t register. I had to look twice. I really can’t express how exhilarating it was to realize that the finish line was within sight. It was just… amazing.

Ironically, continuous progress makes it hard to perceive your progress! In my mind’s eye, the line connecting our boat’s bow to the skyline in the distance was a straight shot. In reality, it was as dynamic as the water beneath us. Distance, in sailing, can be unpredictable. Uncontrollable, unmeasurable. But there we were, near the finish line, riding the wind toward home.

That we were near the finish line was just an illusion.

As we approached the water crib once more, this time to the north, our journey had been nothing but smooth sailing—literally. But within 3 miles of our home harbor, the wind shifted direction and picked up, gusting at 15 knots per hour. And the sea state agreed—3-foot swells and 4-6-foot waves! (Yes, I was at the helm. Confession: I might have accidentally hove to.) 😣

Tacking back and forth for what seemed like hours, our progress stalled. We had a discussion about lee helm (the tendency of a sailboat to turn away from the wind while under sail, the opposite of weather helm – the tendency of a sailboat to turn into the wind while under sail) and then the decision was made: we doused the sails and fired up the motor.

By 5:00 pm, we arrived where we’d started. Sometimes, the journey matters more than the destination. 🌊⛵️