moving to the Caribbean

If you want to go to a place in the Caribbean which is British-owned, you might consider the Cayman Islands or Belise. The Caymans are where many wealthy Americans and Brits store their offshore accounts, while Belize is a poorer country (therefore less expensive). Jobs for administrators are relatively plentiful in the Caymans, whereas in Belise, you may be highly valued, but the pay is much less. Because both countries are British (English speaking), mixed-race children are fairly common. Sorry, I don't know much about crime rates in either place, but you can bet that the more desparate the citizens are, the more crime there will be. The trade-off is the cost of living, of course. Good luck in your search.

I used to live in Antigua its an ex british colony and ticks a lot of boxes

Stay with the US Territories such as Puerto Rico or the US Virgin Islands. The USVI's might be more in line if you don't speak Spanish. Things will be easier paperwork wise. I've lived in Puerto Rico, but I speak Spanish, and in Barbados where I was on a project so paperwork was handled for me. Cost is going to impact you on every island because a lot of people want to or have a second house there so the best plots of land have been taken.

Once again you are up against the same problem as others who have decided to move abroad. How are you going to get the legal right to stay there? You cannot, for instance, decide you want to move to Barbados and just show up and settle. You must apply for residency and prove sufficient income to live, by their definition of sufficient. In many countries you are required to invest a minimum amount of money, or to start a business and employ locals.

Howver, you can move to Puerto Rico or the US Virgin Islands, as they are US territories. It wouldn't be any more difficult legally than moving to Hawaii would have been back in the fifties. They are US Territories.

Hello, I'm living in the Caribbean right now and have been to most. Like Iron Horse and Cynthia said, you'll need to secure employment or set up a business before you come as you'll only be able to stay as a visitor otherwise. If you don't have alot of money then you might want to look at islands like Grenada and St. Lucia. Barbados is very nice but can be expensive. Belize is very natural and close to the US. It is very cheap to live there but a very low keyed pace of life. Employment options would be limited there as well but I'm sure your skills will be greatly appreciated. There's a new government in as well as that might be a plus. On crime, I might be biased but almost anywhere in the Caribbean will be safe. The governments are stable, the people friendly. The usual rules apply, like locking your doors at night. The northern islands closer to the US and Trinidad are worse for crime, the others are fine.

Amazingly, in the past few days I've met several people who used to live in the Dominican Republic. They all seemed to like it. Apparently it isn't too difficult to get residency and a work permit, although there is a waiting list. Take a look at the consulate website and see what you find.

I would suggest you go visit if you can first.
I lived for quite a while in Grand Caymans. Very nice, safe. Paid $2000 incl for a two bed en suite, furnished and serviced apartment sleeping 6 on the beach and Golf course very central area.
Cars are mostly rentals for foreigners.

Everything is lovely, but as most of the Islanders will tell you, one tend to get "Island Disease" where you just need to get away from the Islands for a while.
I do not think that there are that many jobs available on Caymans. A year contract each for some of the clubs bars , diving and sailing etc .
The foreign banks have their own people that gets transfered there.
For the Government and more professional jobs, the Caymanians are very proud as a "family" which provide those positions for their own first and they are very efficient if I may says so.
Foreigners mostly get the lesser paid jobs and shorter terms . Unless you want to invest.

Jamaica too is lovely and really clean in the cities and at the resorts, but definitely more crime. Though they have a few professional jobs available

Cuba I enjoyed , but again crime wise, not where you would want to be.