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.