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Old 26-07-2012, 18:19   #1
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Cruising Boat Selection - Chicago & Caribbean


My first post, so be gentle please.

I am currently shopping for my first sailboat and I would appreciate expert advice ... general or specific.

Here is the situation: I am looking for a forgiving cruising sailboat that I can learn on. It will be located in Chicago for 6 months a year and during that time most of my weekends will be spent sailing, cleaning, and learning. The other 6 months will be spent in Naples. Eventually, maybe in 2-3 years, I will have the skills to travel all over the Caribbean ... I might not come back.


1) Shoal Draft - 4-5' max
2) Sloop
3) Older boat (1970's or early 1980's) - Fiberglass or wood
4) Pilothouse would be nice (my theory is that this will make bad weather more bearable ... yes? no?)
5) 36' - 40' would be enough room I think (4 guests sometimes)
6) The more teak or mahogany, the better.
7) My budget won't allow a Beneteau or Tayana, I might have to do some of the work myself ...
8) Must be able to sail single handed some of the time!!

Here is one I liked (not pilothouse, but ...)

It's a 1982 Gulfstar Sailmaster 39 for $26k

1982 Gulfstar Sailmaster 39 Sail Boat For Sale -

Am I on the right track? What kind of other considerations are there?

I have NO interest in racing. I want a comfortable, safe boat that will take me all over the Caribbean.

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Old 27-07-2012, 10:54   #2
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Location: Bahamas/Florida
Boat: Solaris Sunstar 36' catamaran
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Re: Cruising Boat Selection - Chicago & Caribbean

Robert -

If you like to work, having a wood boat with lots of teak and mahogany will make you happy. Very happy.
Sail Fast Live Slow
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Caribbean, cruising

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