Where in the Caribbean? In general it's not a super attractive place for year-round living. I'd personally go for St Barth, it's the best place in the Caribbea

Where in the Caribbean? In general it's not a super attractive place for year-round living. I'd personally go for St Barth, it's the best place in the Caribbean. If you're an EU citizen, you can just go live there without any limitations. If you're an US citizen, you're theoretically limited to 90 days but this isn't actually enforced. In any case, visas are the easy part. If this is a serious question and you are wealthy, https://reddit.com/r/fatFIRE https://reddit.com/r/fatFIRE might be the best place to ask.