Best Caribbean destinations with an old-school, understated feel

[Liminlinda]

What are some of the best Caribbean destinations? We like old money and old school vibes, not Mykonos or Santorini type people

You'll need to be more specific about what you are/want - what do you mean by 'old school vibes' and that you like 'old money'? And no idea what Mykonos or Santorini people are like!

Virgin Gorda - Bitter End Yacht Club

I assume you mean specific hotels rather than regions of islands/entire islands? Maybe Jamaica Inn or Golden Eye resort, Ocho Rios. We had kids with us so these didn't work and we ended up in Negril, but these are more traditional resorts. We also looked Colony Club in Barbados, but then the airline pulled out of the route, so not yet been there either.