Hi Bryan, thanks for the update. On one hand, sorry you got laid off from your job, but on the other hand, YAY! More time to sail!
I did the trip from Chicago (from Crowley's Yacht Yard) to Holland, MI (to Eldeans) last June aboard my 27' Newport, which is similar in size to yours.
The planned rhumb line was 87nm, but our actual trip turned out to be 100nm. It took us exactly 23hrs, 49mins, 55 secs, exactly, from cast off, including the time it took transiting under the two bridges on the Calumet River between Crowley's and Lake Michigan, until we tied up in my slip at Eldeans. During the night, we slept in 1-hr shifts leaving 2 crew awake while one lucky guy got some shuteye.
We left about 8pm on 6/12, and got in just before sunset on 6/13. Oh man, there is nothing in this world like setting out to sea on a cool, dark evening. In our "rearview mirror", the gorgeous skyline of Chicago and a setting sun, and in front of us, the black horizon of a seemingly endless freshwater lake.
We took more of a circuitous route than we had planned to take advantage of a favorable wind direction. While we could've fired up the engine right out of the gate, all three of us decided we were really eager to try our hand at nighttime sailing. It was a beautiful, moonless, starry night, and we cut the engine to really soak in the experience; bright stars in the sky, the boat enjoying a spritely beam reach, with little chop on the Lake. As the wind began to die off the next morning, we fired up the engine just to make sure we got to the marine in time to catch our ride back (my fiancee met us at Eldeans to give us a lift home). I brought my camera on my trip, and forgot to take any photos. I was so in the moment, I just forgot, completely.
On our GPS track, its kind of amusing to see all of the changes of tack, and accidental course changes. Man, we were SO sleepy!
It was a blast, but just looking at the track we took when we passed the Calumet Harbor breakwater and motored into the wind to raise our [hank on] jib is kind of funny. A well-choreographed racing crew, we are not!
Later in the evening, after a sleepy change of watch, someone accidently tacked and noone noticed for 15-20 minutes. I think I was asleep at the time, so the blame must fall on one of my crew (thats my story, and I'm sticking to it).
There is definitely much of your trip where you'll be out of sight of land, but always on a clear night you'll see a faint glow to the West which is the light pollution from Chicago.
I will say, the middle of Lake Michigan is much, much colder than you'd think. When we left, as we were prepping the boat for departure, it was around 82* dockside at the yacht yard, and incredibly humid. It was so hot and humid we left our extra long underwear and cold weather gear in our cars at the yacht yard and packed extra shorts and tshirts, planning to be sweaty and sticky most of the way. Big mistake! At midnight, in the morning of 6/13, somewhere about a third of the way between Chicago and Holland, MI, we recorded an air temperature of 57*! So, be prepared for either extreme.
The next morning, the pot of coffee we made really boosted our spirits, and gave us a lift. We couldn't see land in any direction (although we were close enough to shore that we should've been able to make out shorelines and watertowers) because of a thick fog that didn't burn off until around noon.
Sailing into Lake Macatawa, as you pass the Big Red lighthouse, was the most amazing feeling in the world. There were people out enjoying the pier and breakwater at the channel mouth to Lake Macatawa, and everyone waved at us as we were coming in. On your left, as you enter, is Holland State Park, on the right you'll have a closeup look at Big Red, and then quaint cottages and private homes that are a marvel.
My only advice is to plan for enough time to really enjoy your trip. Don't get in a rush. Sailing and schedules don't mix. Let the weather do what it will, and be flexible.
And lastly, bring a camera (and remember to use it) and an extra battery and share your photos with us when you check in again!