I think your painting with too broad a brush.
I paid under $2000 for a 32' 30 year old boat and it came w/ a kubota 4cyl. w/ less than 200hrs. all bronze through hulls. swageless rigging etc etc. there are alot of boats around and alot of people who want to part w/ them .
As for the distances from fla to the Bahamas, I think bimini is 48 miles away !! an overnight sail.
Also to say an inexpensive neglected boat is not or would not be "sea worthy" is too general a statement .
I could sight dozens of examples of folks sailing far on less and w/ less.
I'm exhausted with the repeated mantra of and from folks about how difficult and dangerous sailing is and how one needs a certain boat and equipment. It just isn't so, please quit perpetuating this mistruth. how many accounts of completey inexperienced sailors making long trips and extended cruises successfully will it take to show sailing is just not that rixky or complex?
And the "classes " and "courses" are SOOOOOooooooooooooooooooooooooo lame. just read a little and take an interest in it and you will learn /know all that you can without actually doing, after that doing will expose the rest.
I've sailed the hell out of my $2000 dollar boat and she has many more miles left in her.
just do it, do it.
Haha I appreciate your confidence and go-for it attitude, helps rekindle mine. I do think we'll err on the side of caution though since none of us have any background in this whatsoever. We'll certainly be putting out ads for labor in exchange for experience. I like this because we'll learn both sailing and maintenance.
As far as expected costs, we really don't know. I have been seeing very reasonably priced boats, but many look to need some work. Since we're in Oregon, about as far from the Keys as you can get, we'd rather buy something that needs little to no work at all, that way there's no big surprises when we go down for the trip. I'm not sure how we're going to work out logistics, but we were thinking of buying a boat online in the keys... sight unseen. This is a big risk, but we were thinking of having local forum members maybe help us scope out the ship beforehand. It would save us the drive/flight and thereby a LOT of money.
What other kind of factors go into a trip like this? Any recommended reading for us? Thanks for all the replies!