Cruising Boat Selection - Chicago & Caribbean

[robertscruiser]

Hello,

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.

Criteria:

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 - www.yachtworld.com

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.

Regards,
Robert

[FSMike]

Robert -

If you like to work, having a wood boat with lots of teak and mahogany will make you happy. Very happy.