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post #6 of Old 06-07-2015
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Re: Intro, Lake Michigan Advice, Questions.

There are many wonderful harbors on the southern end of Lake Michigan: Chicago (of course), New Buffalo, Hammond (nice facility, not great surroundings unless you like the casino), St. Joe, and South Haven (beautiful, but a touch further north).

I think with 10k and patience, you can get you something seaworthy in the 30' range. It would be a hunt, but very doable. I know someone who just a year ago bought an Irwin 30 for ~$2000. The boat was in fine shape; it had been donated to charity. The charity auctioned the boat, and his bid won. It might have been the only bid.

Alternatively, when I search Yacht World (narrowing the search to Great Lakes, Michigan, Illinois, and Wisconsin), there are many boats in the 10-15k range. They do need updating--things like new cushions and leaks around fittings fixed and things like that. But, you CAN find boats that can be safely put into the water. Of course, pay for a good survey as part of the buying process, as I'm sure some of these boats also have serious problems. Catalina 30s, the Chevy Cavaliers of production boats, come to mind in this "genre" of boat.

With respect to gaining experience--folks who suggest a small boat first near your home are wise. That's how I started. However, you could take a 3 day bareboat certification course--something like through Sailboats Inc. in Chicago, or Michigan City Sailboat Charters in MI City, IN. After a course like this, and then an overnight bareboat or two (daysailing and docking nightly at the home port), you could responsibly begin thinking about owning and skippering your own boat.

Sailboats Inc., back in the day, was a legit company with an active Chicago base. Although they're still around, their fleet has shrunk considerably, and they don't regularly schedule instruction (I think it's on demand if and when they have interest). I believe Michigan City Sailboat Charters is a bit more active these days. Doing a three day class through a similar company like this is mini-vacation. There aren't a ton of such companies on Lake Michigan, but there are a few (maybe also one in Traverse City, MI).

Couple the cost of the class, with say two bareboat charters of 2-3 days each, and you are still WWAAYY ahead in terms of money spent that first summer relative to what you'd have spent just on slip fees, insurance, maintenance (not even counting the purchase price).

Good luck!
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