To destination or not!?!

So my baby sister is getting married next May. Like most brides she is looking through all the books in search of that perfect dress. She's narrowed it down to a few different styles and has her colors picked out too. I'm going to be fixing Save the Date cards for her, and then later the formal invitation as well.

The only thing not totally clear is where to have it! Now she's going to get married in May so the weather will be getting warmer (we are in the south) so she's thought about an outside wedding. However, with the way the spring is in the South you never know if you're going to have an unexpected downpour at any minute that would flood the entire party.

So I've been trying to talk her into a destination wedding. Just inviting a small group of the families and not being too elaborate. I keep telling her that we could do beautiful beach wedding photos and that it would be really fun. She's open to the idea but I think that she's also kinda scared about it. We've talked about Hawaii, Jamaica, Florida, and most of the Caribbean as well.

So has anyone done a destination wedding ... where did you go ... what did you learn ... what advice would you give ... and would you do it again?