I had to put in a claim on trip insurance for a cancelled trip to St. John last year, due to the fact that I got pregnant after booking and my due date was the week of our scheduled trip! I've always purchased insurance but this was the first time I had to file a claim. The process took a lot of my time, between getting all the necessary receipts/proof of payment/doctor's statements, etc., but in the end, we got MOST of our money back (although not everything.) All-in-all, though, I was pleased with the result ... it was better than losing all the money paid for villa deposits and airline tickets! I don't know what they cover as far as hurricanes, but we used Access America. The villa company also refunded a portion of our deposit. I think they have certain refund rules as far as hurricanes, but I am sure they vary by company.

Check with your credit card company, if you have a good one, insurance may be included if you use that card to book the trip

If you have not tried "insuremytrip.com" - you might plug in your dates to get basic comparison info on several major companies. Then you can verify the info with your top choices. We sometimes get insurance, based on where, when, how much, etc. I have used a couple of different companies, but fortunately haven't needed to file any claims yet - sorry, no info on that.

Is there a trip insurance that you can customize? I just would want villa and plane ticket with car rental coverage? Or do you have to take all the extras they tack on?