Are we crazy? (please be brutally honest)

[rookiemoon]

I've been hooked on this forum ever since my wife and I have been trying to plan an extended stay in Caribbean for our honeymoon. We both want this trip to be as much of an adventure/learning/bonding experience as possible. We love the idea of island hopping with a roof over our head. But are we realistic is my question to you gracious readers.

Here is the scenario in detail:

-We have no real sailing experience to speak of(I can sail a sunfish on a small lake with ease ).
-We don't have much mechanical repair skills to speak of.
-My Grandparents spent 20 years living on and off of their sailboat, live in Tampa, FL and could teach us (though I want to ask your advice before I hit them with our bold plans)
-We have a budget of $5-$6k for purchase and initial repair of a sail boat with a sleeper cabin
-I've noticed that on Craigslist in Tampa there aren't any shortage of sailboats for sale (and in the water) for $2-3k
-We need to find a cruiser that can handle a trip from Tampa to the Caribbean and stay in 1 piece
-We can afford to budget $1000/month while we are out exploring

What do you experienced sailors think? Is this idea insane or just so crazy it could work?

P.S. Another hypothetical option would be to buy a sailboat in the Caribbean if it would be more realistic and cost effective. Then however we would be passing up the wealth of knowledge my grandparents have to offer on the subject...

Thanks in advance for any opinions you share