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Old 04-07-2008, 07:26   #1
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Day Charter in Chicago?

I will be in Chicago in the middle of this month with my family (4 total). Does anyone have recommendations for a day or 1/2 day sailing charter? This cruise is intended to give us a preliminary indication of how much we will like cruising. I am interested in something around 32-36 feet. At some point in the future, I hope to buy something in this range for coastal cruising.

If things go well for me and my wife (kids nearly grown), we may eventually go farther afield.

Thanks,
Ron
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Old 06-07-2008, 05:52   #2
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Here’s a couple of charter possibilities.

Chicago Sailing - Private Sailing Trips in Chicago customized to your needs

Windy City Sailing Charters and Events
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Old 06-07-2008, 19:05   #3
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Thanks Gord,

Are there any special characteristics about these two that set them above the others?

Thanks,
Ron
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Old 06-07-2008, 20:06   #4
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Ron,

Most of what you will find in Chicago proper will be captained charters. There is little bareboat in the city. What Gord has offered is two of the few that are there, and I believe that both will be with a captain only.
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Old 07-07-2008, 04:48   #5
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Thanks Tommy,

A captained charter is perfect for now. My experience is only with beach cats.

Ron
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Old 07-07-2008, 20:16   #6
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There is a company called Fairwinds that has a new 40' I think beneteau. If your thought is to convince your wife that life on a boat is great, that may be a good place to start.

Good Luck, and I agree, out of Chicago, if unfamiliar, a captained charter is the best option. If you can do it at night you can buy anything you want with that skyline as a backdrop.
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Old 18-07-2008, 07:32   #7
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Thanks to GordMay and tomdidit for the charter recommendations. Unfortunately, I was not able to schedule anything due to time constraints (or priority problems). I hope to get my wife, who is definitely interested, on a boat soon. We both love beach cats and think that a cruiser will be part of our future. We just want to take "baby steps" on the way toward a purchase.

Thanks again!
Ron
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Old 18-07-2008, 10:26   #8
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We both love beach cats and think that a cruiser will be part of our future. We just want to take "baby steps" on the way toward a purchase.
Yes, it's a great idea. Try to pick a day when the sailing and weather are good. You need a few of those so you remember what it can be on those days it's not.

Something cheap is training classes. ASA and US Sailing have schools every place (well almost) and you can even do a course as a live aboard or some place near a place you want to go. It's a great way to sail real boats and learn about it. familiarity makes it comfortable.

If you can get through a charter or two and/or a class I would think you can decide if you like it enough to get into it more. The way to know for sure is it really all is supposed to be fun. If you can try different things and say it was a great time after each of them then it's probably a good fit.
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Old 21-07-2008, 07:26   #9
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Thanks Paul, I have considered a school, but have not yet looked at the details. It is good to know that they are nearly everywhere. Maybe We'll try one on the east coast somewhere.

Ron
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