Really depends what you have in mind to do and budget. I have lived in the Caribbean for 7 years in what is considered the safest island (Cayman). Some troubles at night the past couple of years that are generally well under control (few bar fights here and there, shootings are under control - had a spate of gang shootings in 2010 but they all killed each other so problem solved) but very safe during the day and evening and a great beach, fabulous restaurants and stingray city...other than that....uummm....bar anyone? Its a very Brit-ccentric mini-Miami so unless you nip to little cayman do not expect a desert island! Plus rather pricey. Do not go to Jamaica. Armed guards to go anywhere outside a resort (real shame as Jamaicans are wonderful people). And many of the Caribbean islands frankly are a dump. There are some gems out there though, I would consider island hopping by boat or a local putput plane airline on the main chain of islands that run north to south - perhaps start at BVI, Puerto Rico or St Maarten (watch in case they route you via miami to get there, be warned, but st maarten does have an excellent airport and inter-island flight network, even though i really do not rate the place) and work your way south to better islands, 2 or 3 days on each is MORE than enough before alcoholism sets in.

One island to look at if just wanting one island is St lucia. very scenic, peddlers are present but not aggresive (in cayman they are locked up so we do not have any, other than downtown taxi drivers...). They have had some violence in the recent past as well - best place to check out the caribbean overall for safety is http://www.fco.gov.uk/en/travel-and-...ntral-america/

That being said, in my honest opinion I would go to Hawaii if the points stretch that far (Kauai'i especially). Note if you go via DFW you can get to two islands i think (Maui and Oahu) from there on a 763 with AA so at least some form of slanted flat bed (the 757 routes with aa from lax are very old first class - i.e old leather armchairs for day flights only and some return flights start late at night for a 5/6hr hop to la), and island hop with hawaiian air from/to those islands to Kauai'i / Maui. Long journey, well worth it.