As I mentioned before, we signed on in late August with SailTime Chicago, a fractional membership sailing club, and have enjoyed several outings in Lake Michigan since then.
The club keeps their boats in Burnham Harbor in Chicago during the sailing season, but winter is coming and it’s time to move the fleet up to Waukegan, IL, about 50 miles north of Chicago. It’s a bit of an endeavor and they don’t have enough hands to do it themselves, so they rely on the support of the club members to get the job done. When the call came, I said yes!
I drove to Waukegan on a Tuesday evening and spent the night in a hotel. Wednesday morning, I took the Metra down to DT Chicago, about an hour’s ride. Once at the transit center, I Ubered over to Burnham Harbor and hung out at the marina until the others got there.

Ryan, Micah, and Davida, showed up at about 9:30. Ryan is the fleet manager for SailTime and Micah and Davida are his assistants. Our mission for the day was to move two boats up to the marina in Waukegan, signaling the end of the sailing season.
I boarded a Jeanneau Sun Odyssey 349, “Red Sky” and would travel with Davida, a licensed captain. Micah, also a licensed captain, was going to sail the other boat solo so we decided to stick together – to buddy sail – to ensure everyone’s safety.
At 10 am we set out from Burnham Harbor under motor power and headed out into Lake Michigan. The winds were southeasterly at about 13 knots and the sea state was pretty intense, the waves were about 6 – 8 feet. (These are the kind of conditions that can make a gal fairly seasick, but I applied a scopolamine patch the day before so I was in good shape.)
I was expecting a quick and sporty sail but with the conditions such as they were, Micah decided to motor the whole way rather than try to manage the sails by himself. Since we were buddy sailing, we motored too. If we’d have hoisted the sails, we’d have gotten way ahead of Micah.
For the last hour of the journey, we were right on track with Micah, so Davida thought it might be beneficial to unfurl the jib sail. We were getting tossed about by the waves, he reasoned, and the jib sail would catch some of the wind, heel us over slightly, and reduce some of the motion. It turned out to be a really good move!
Using sails to manage the motion of the boat (and the quality of the ride) was a new concept to me. This is one of the things about sailing that is so interesting – I can’t get over the body of knowledge that has developed over centuries of sailing. We think we live in such a highly technological age, and sailing might appear to be so basic. But it is certainly not basic.
It took us 5.5 hours to reach our destination. We approached the marina in Waukegan and pulled up to the dock. I wasn’t able to see how Micah managed it single-handed, but when I asked, he said, “I went very slow….” When it was our turn, Davida approached the dock slowly and when we were close enough, I just hopped off the deck and quickly tied a bow line to a cleat on the dock. Davida took time to tie off the rest of the lines and spring lines properly and the job was done!
My car was parked at the station on the next block. So I walked over and drove home!
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