Best place to buy in the Caribbean?

[brownoarsman]

Getting close to the time when I'll begin the boat buying process, and have a couple of questions for the kind sailors here: Outside of the USVI, BVI, and possibly St. Martin, are there any other places you'd recommend a US citizen buy a sub-$20,000 boat? And secondly, where are the best sites to research such boats (we've looked on Craigslist, Yachtworld, Sailboat listings, and individual brokers' sites, but selection hasn't been huge, and we would really like to get at least three very good prospects in one easy location so that we don't waste a flight out).

The situation is that a friend and I will be buying a cheaper sailboat and intend to cruise the Caribbean from December to April. We have both been members of a sailing club and have done week-long cruises in the BVI and in New England, as well as a ton of overnighters and weekenders. We were originally going to buy in Florida and start with the Bahamas, but then thought that, in our price range, there might be a number of boats in the Caribbean that aren't worth the price of delivery back to the US and that the owners don't want to sail back themselves, and where the owners (or heirs) are in a hurry to sell. Initial research reveals that this might be the case, and that the best places to buy (greatest number of sub-$20,000 boats) are in those places mentioned above.

A few complications: We may bring the boat back to the US so would like it to be US-flagged in order to avoid import duties. Neither of us have ever bought a boat before and while buying US-flagged appears straightforward in the USVI/BVI with a cooperating PO, we have no idea what might be entailed in islands further afield, and whether a broker can ease that situation for us. Our goal is to sell the boat at the end of this small cruise without losing A LOT of money, we're happy to lose a bit though. This is the main reason we're looking at a sub-$20k price point, we could go higher if we thought we could sell it again quickly without a large ($5k+) loss at resale. If it doesn't work out, we may still just buy in Florida and focus on the Keys and the Bahamas.

Thanks for your help and hope to join you on the water soon!