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There are lots of boats available in Florida.

coming South, unless you intend to take the outside route, you will likely want to leave the States from Miami.
Many sailboats wait there for a window to cross the stream.

Just thinking you can find an experienced Caribbean boat down here... ready to go.
There is wisdom in this, many Caribbean sailers leave their boats in that area and can never recover them due to health/age. Lots of deals to be had for a boat that's been sitting for a couple years and just needs a good cleaning. I've heard st maartin is the best place in the world to refit a boat aswell.
 

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Bombay Explorer 44
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I've heard st maartin is the best place in the world to refit a boat aswell.
Hmm I am not sure about that. It is a duty free area which is good but you are in a hurricane area which is seriously bad. Also if you need outside assistance the prices are high which is in part due to the number of megayachts with deep pockets in the area.

No for a minor refit I would choose Carriacou. Best little boatyard in the Caribbean with a good ali welder and a good engineer on tap if needed.

But the place to go for a major refit has to be Trinidad. There is almost nothing that you can not get done there and the prices are significantly cheaper than anywhere I found up island.

EG when I was looking to paint my 44ft monohull the lowest quote I got up island was $10.,500 plus materials. I had it Awlgripped in Trini for $3.400 which INCLUDED materials. Sanded down 2 coats epoxy primer 3 coats Awlgrip and a bootstripe. I have a vague memory of the St Martin estimate being stratospheric maybe $20k +.

Chris Doyle who compiles the popular cruising guides had his catamaran Ti Kanot built in Trini.
 

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Captain Obvious
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Don't discount the value of accessories and gear. I'd look for a boat that had a wind generator, solar panel, autopilot, chart plotter,refridge,dodger, nice dingy with outboard. Look up the price of each of those things when you consider the boat. Those things can add up to half the value, and maybe more, of the boat. Plus they indicate that someone with money had the boat and cared about it.
 

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Just google "sailboat for sale florida"

It is the way I have been researching the different makes and prices of sailboats. You can pick and choose the state you want and, if you click on the sailboatlistings.com link, the listings comes up by length from longest to shortest. Page forward to the length you are interested in and start looking. It has given me some great information and insight into the many different makes and styles (plus prices).


And this guy has a nice write up on how to talk to a seller and look at a sailboat to decide if you want to continue - or hire a survey for it. Marine Survey 101, Do your own marine survey
 
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