Hi all. I chartered with Brent (Island Fun) a couple of years ago, and had a very good experience. He has a few rules that other operators don't have, but they make sense for an operator of his scale, and he's quite straight-forward and upfront about these. Basically, if you stick to your agreements with him, he'll look after you just fine. If not, then I gather from these boards that you can expect to hear from him about it. Overall, his boats are older and more basic than you get elsewhere, but they are well-maintained, clean, functional and do the job - everything worked like a champ on our trip, and no maintenance calls were required. And I don't believe you can beat his prices anywhere in the BVI.

All that said, the thing I think you do need to consider is operating the boat with just 2 people - not always easy. For instance, Island Fun has a 1200+ sq foot mainsail, and it's heavy. We had 2 strapping college boys in our crew to haul it up, but I wouldn't have fancied doing on my own too many times. The smaller the boat, the easier you are going to find it to operate (hauling sails, maneuvering etc). You might also want to think about paying a little more to get electric winches - SailTMM has a couple of Mahe 36's for <$4000 in low season.

Have fun, whatever you decide!