Thinking About Buying a Boat...

[newbie24]

I just moved to Chicago and am thinking about buying a boat. I have some questions and was hoping to get some help here. First of all I have some cruising experience down in the BVI and St. Martin but I have always sailed with my father. Now I want to buy a boat here in Chicago but, I don't know what cruising around here is like. I am looking at something in the 30' range and feel pretty comfortable handling a boat that size, but in waters I already know. So... I guess my question is what do you recommend I do prior to buying, so I am prepared for sailing around The Great Lakes?

[S/V Illusion]

One option you might consider before making a substantial capital investment with no real experience is to crew on someone's boat for a season. The chicago area is full of YCs where you can find a boat on which to crew during the racing season where you'll get some invaluable experience and develop lots of sailing friends from whom you can get some reliable advice from people you know rather than over the internet...

Aside from the sailing experience, you'll quickly learn what it takes to maintain a boat which can be a real epiphany to the uninitiated. And then there are the op expenses.

[newbie24]

How much time commitment is that? I travel a lot for work, but that sounds like a lot of fun.

[S/V Illusion]

A few hours on weekends although there is the Chicago to Mac race at the other extreme of 330 miles. Most of the guys who crew on my son's boat don't show up every weekend or Wed night which is why the opportunities are so wide for folks like you who have an interest but not a rigid schedule to devote to sailing- skill levels also vary widely.
A YC is a great way to get involved in the sailing community with the side benefit of likely being among the first to find out about good and reasonably priced boats for sail as well.