Well I am glad someone moved this here to be in it's own post. Generally it is better to start another thread than to side track someone eases. I think perhaps you need to be a bit more clear as to where the boat will be and what your plans are with the boat before you get a conclusive answer. Some of your posts have been kind of all over the place. And I am not sure what deslimg means.
There are a couple of different Islander 36's and the other thread was about a quite different boat. assuming this is your boat:
ISLANDER FREEPORT 36 sailboat specifications and details on sailboatdata.com
The Freeport is an almost pilot house or deck salon design. With the big windows, it looks like a great boat to do some coastal sailing on. While they make for a very airy living space, they are susceptible to being stove in by waves so I am not sure I would consider it "blue water" style boat. But the Caribbean is not really blue water anyway. Most spots are always in sight of land, so really more coastal and the type of sailing this boat was made for. They call it island hopping, not island passage making for a reason. If it is not already in the islands it might be a slog to get it there, but if you pick a good weather window should be no problem at all. Bob Perry the designer, frequents here so hopefully he will chime in. You might send him a PM if he does not respond here once you get enough posts. (I think it requires 15 posts to send a Private Message)
Here are some reviews from this site:
Freeport36 - My Product Gallery