I think your choices are pretty countless: search online and see what your heart desires then check that your wallet is fat enough ...
Remember there will be some relationship between the size of the boat and the resulting costs of berthing, equipment
You will need some money
for cruising each year, so do NOT overspent on the boat.
If you are handy (very) then you can get an older boat in less than perfect (still preferably good) condition and fix all and any non-critical/structural matters. This may come out cheaper and you will learn about your boat a lot, which in some cases may be a bonus.
If you are not, you will probably go for a boat in good / sail away condition.
Avoid old, heavy boats with plenty of peeling varnish
outside and rusty motor
inside, unless this is what fits your dream best. Some people find more pleasure fixing than sailing.
Some boats are easier to re-sell than others, if this may count to you, buy a boat with good re-sell market.
Do not limit your search to the Caribbean
, you can easily buy a boat on the other side and sail her to the Caribbean