I figure the best way to start planning this would be to ask first.
First, is this even possible in my size boat - 1999 Crownline 225
cuddy, 350 Mag/BIII? On my charting software, it looks like 75 miles
from South Haven to Chicago, but i can put in somewhere else if it's
easier/shorter. I've heard it's a 50 mile trip. I would leave at
first light to take advantage of hopefully calmer water. What else
should i bring in addtition to the usual/required gear? Spare VHF and
GPS? Spare engine parts (belt, fuel filter, impeller, hoses), tools,
? I don't have, and Crownline says you don't need, trim tabs, but i
can't help but think they would help in bigger water. Any/all
suggestions welcome. If it turns out this boat can't handle it, i
have no problem waiting a few years until i step up.

Thanks, -JZ