This post may contain affiliate links*

Crossing the lake to Chicago

Spring 2023, our 1st BIG trip of the season

Crossing Lake Michigan, the 3rd largest Great Lake, is daunting.  Worry and fear can paralyze action and exploration.  Our planning and preparation can never be enough.  The danger of the cold deep water and the ever changing weather that can unleash life threatening conditions in a matter of minutes will deter many – even seasoned sailors from attempting such a journey. 

I felt all of this – and more – as we geared up for our 1st ever solo Lake Michigan crossing!

Kyle + Kara selfie with sun and New Buffalo harbor in background

We’re working on studying and learning the weather patterns in our area.  Kara and I each have different and multiple weather and wind predictor apps that we review regularly so we can pull in as much information as possible, and then sift through it trying to figure out what is most likely going to happen.  Predicting the weather is something that most “experts” get right only ~50% of the time, so us amateurs have a lot of work to do.  The only thing we truly know about the weather is that there will be weather outside! 

Kara standing in front of Monroe Harbor

From our days and weeks of studying the weather, we believed we had a good weather window to cross Lake Michigan, stay in the Chicago harbor for 2 nights, and come back across the Lake to New Buffalo, Michigan before any storms picked up. 

 Earlier this year, Kara and I took a road trip to Chicago on land to scout the various Chicago Harbors (there are 10!).  We decided we wanted to stay in the mooring field at Monroe Harbor because of its proximity to the city parks and walking trails downtown. 

Because we were new to tying up at a mooring field and navigating around other boats, we wanted to experience the Chicago Harbors before Memorial Day weekend to increase our chances of less boat traffic.  So we planned this trip very early in the season, and we were prepared for the cold, or so we thought!

As the day to cast off got closer, we nailed down all of the preparations as best we could think of – daily reviewing weather conditions, checking our safety gear, making checklists for food and clothing supplies. 

Kara bundled up at the helm

SV Zeke E Boy was more than ready for the crossing – but were we ready?!? 

very faint Chicago skyline in the distance of Lake Michigan

Having the courage to disembark and leave the safety of the dock and our “comfortable” sailing area along the southeast coast of Lake Michigan (always with land in sight) now has new meaning for me.  Not being careless or arrogant, but growing with the experiences and learning to trust our boat, our equipment and ourselves takes a lot of courage.  Overcoming self-doubt and second-guessing is hard.  Is the boat ready?  Can we make it?  What if something happens?  Kara and I, together, pushed through the unknowns and decided to make the trip!

To get more comfortable and settled, we stayed on the boat the night before we left.  It makes getting up and getting the boat ready the next morning much easier – especially because I wanted to leave by 4:30 / 5 am!  We try to keep our normal morning routines – coffee, breakfast, devotions, etc. and getting ourselves physically, mentally and emotionally ready for the journey. 

One last check weather check before leaving, and our weather window looked good.  There were no storms predicted until the day after we were planning to return, and the wind was predicted to be within our comfort zone.  We then went through all normal boat preparations and left the dock on time for our first lake crossing!

We couldn’t have planned a more perfect day – weather wise for our 1st solo crossing!  Thank you, God! 🙏 It’s 47 miles across the lake in perfectly calm conditions, and no fog!  We decided to motor because there wasn’t any wind!  It took us over 7 hours to reach Chicago’s Navy Pier harbor entrance.

SV Zeke E Boy with Chicago skyline in the distance
Kyle at the helm with freighter in the distance

We saw very few other boaters during the crossing – only a few fishermen and one freighter in the distance that passed behind us – luckily!  As we calculated its speed vs ours, a 30-minute delayed start time on our part would have put us directly in line and we would have had to divert out of its path!  Another answered prayer! 

The Chicago skyline is magnificent!  We got to enjoy an amazing trip there as well as explore the city for a few days.  I promise to share more on what we did and our adventurous trip home very soon!

Chicago skyline view from SV Zeke E Boy

Tell us what you think

Let us know what you think of our sailing adventures by sharing your feedback in the comments below. How do you build your courage to overcome staying in your comfort zone? We’d love to hear from you! 

– Kyle from Zeke Life

Live like Zeke
You’re such a good boy!

Kyle looking at Chicago sunset from SV Zeke E Boy

*Zeke Life participates in the Amazon Associates Program, which will allow us to earn money on products purchased from some of the links provided. We will only recommend products that we love and use regularly!

Similar Posts

One Comment

Leave a Reply

Your email address will not be published. Required fields are marked *

one × four =