The answer to that question is probably. I bought an O'Day 25 that's in Michigan City and I plan on sailing it to Chicago or Waukegan, IL in the spring. The boat has a bunch of sails (working set is in excellent shape), the starboard bulkhead will be replaced before launch, 25w VHS, 3w handheld, Saildrive (see my post other concerning this), head furler, working head w/tank, bimini and a whole lot more. My main concerns at the moment are that I have near zero navigational skills. What would you suggest I buy, read, learn, test etc before doing this trip?
Mayhem,
You have nothing to worry about. I bought my first boat (Hunter280) in Milwaukee and took her to East Chicago, Indiana. Had zero experience. Worst of all possible conditions the day I left Milwaukee ...38 F, sleet & rain, 20-30 knots from the east (I am sailing down the west side of Lake Michigan). I made it, but did learn to pay attention to wind and weather.
Bought my second boat in Holland, MI and took her to East Chicago. Had more experience on this trip, but had engine problems out of the gate. Had to lay up in a river marina about an hour south of Holland. All ended OK when I made it home the second day.
There are several marinas between Michigan City and Chicago or Waukegan. Michigan City to East Chicago Marina is a day sail (about 20 NM). EC to Chicago is about 20 miles (spend the night anchored in “the play pen”). Chicago to Waukegan is about the same I think (maybe even shorter). On my trip down from Milwaukee, I spent the night in Winthrop Harbor on the Wisconsin/Illinois border. I made it home to East Chicago from Winthrop Harbor in one LONG day.
Also, it is hard to get lost since you can see Chicago from a loooong, looong way on the Lake. Use it as a landmark and you can’t go wrong (unless there is no visibility).
A compass heading of 343 degrees should get you from MC to Waukegan, but it is about 55 NM,
If you have an iPad or iPhone, you can get a free (or cheap) nav program called iSailor. Uses free maps and while not perfect, would keep you on track while on a Lake Michigan. Or get a small handheld GPS.
Stop by the East Chicago Marina and I will buy you a beer and point you in the right direction the next morning.
I took charter lessons in Michigan City with Michigan City Sailboat Charters. Beautiful marina.
I assume you won’t be shoving off until next year at this point. All of the marinas are closed now for the winter.
Good luck on your adventure (and no, I don’t think you are [too] crazy).
Greg