[ericthered]

So you're playing with two elements that are all over the Caribbean, but usually don't happen in the same places: criminal behavior and resorts. The criminal behavior is usually concentrated in places tourists will never go.

Trinidad doesn't have much of a resort industry: the vast majority of that is on Tobago, which has a much different feel. If you want a lawless area in Trinidad, I'd recommend Laventille, just east of Port of Spain. That won't feel like a resort, though Port of Spain does get visited on cruises.

If you want a private island, My mind goes to either the Bahamas or the Grenadines, and for what you want the Grenadines (part of St. Vincent and the Grenadines) is probably superior. I'd say that St. Vincent is more out of the way than most of the countries in the Caribbean, but they picked up an international airport in 2017, so that's changing. Before then you had to stop at other Caribbean islands first to get there, by boat or using a turboprop run by a local airline called LIAT that in my head stands for "Late In All Terminals". The Grenadines are pretty separate from st. Vincent, and I don't think the government is going to complain much if you rent an island and tell them your own private security will handle things, as long as you don't make the news. At which point they'll skip the police and call in the military .