Intro and question/opinions please

Have been lurking here for a while and you seem to be a knowledgeable lot!

Anyway, I have a life-long desire to cruise the islands of the Caribbean. I have taken a basic safety and boat-knowledge course, and have had some experience in small (17') motor boats. Of course I'd rather learn to sail and do it that way but it doesn't seem do-able due to a bypass op four years ago, I have little upper body strength, so have decided to try a 40'+ diesel trawler/cruiser-type boat..

I live in New Orleans.

The boat would have to cope with two people (Me and the wife).

I have read about the need for hard-copy charts and flares here - thanks a lot - have that all in the memory banks.

Does a boat have to be in perfect condition to be able to island hop? I read that such and such boat 'needs some soft spots addressed' and, without actually going to look at the boat, am a little put off by something less than perfect condition! But my car runs even tho there are things that need to be addressed etc..

The thing is, do I need years of experience to simply buy a suitable boat and just 'do it'? Or am I being a bit simple?

I am resourceful, relatively intelligent, an engineer by trade and want another adventure - as if Katrina wasn't enough!

All advice gratefully received.

Molesworth.

That might do for a 'taster' as it were, but I was thinking of 1-2 years cruising..

Thanks tho'

Molesworth