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?