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It depends on the type of the boat that you need. I only can advise you one carribean rental sailboat, I'm don't know if it will helps you, but you can rent a yacht in the caribbean there. Their service is quite nice and I have never had any problems with them. So if this variant suits you, you may choose any rental carribean yacht that you will like.

Thanks for the link, Paully. Me too, I often go sailing but now I'm looking for a new company with cheap prices. I hope that yours isn't very expensive.