Indiana Sailing
Might try the Eagle Creek area in Indy. A while back there was a weekly racing and a number of sail boats, but I don't know about rentals. To the south a bit, try the Lake Monroe Sailing Association (there is a web site and a Yahoo news group). Might be able to get some sailing with one of the members (many from Indy). LMSA does not have rentals, but does have sailing classes for kids and adults. The marina at the 4 Winds Marina on Monroe (or a vendor of some sort) rented small sailboats (Hobies, etc.) a few years back,but I don't know the status of that operation at this time. A number of sailing folks keep boats at that marina as well.One other possibility is the Bloomington Yacht Club on Lake Lemmon, just north and east of Bloomington. I have no knowledge of their activities, but sailing there seems to be limited to small pocket cruisers and day sail activities.Of course, charters are available on Lake Michigan and the other Great Lakes. You might also contact Sailboats, Inc. in Indy. They may know of other options.