To never be able to visit any of those places is too depressing.
What constitutes the same place? The same resort? The same island? The same collection of islands? The same region? Use Hawaii as an example. Can I go to A different part of one island or a different island? Or once I go to Hawaii at all, it’s off the list?
That might change my opinion because I’m going to run out of places to travel that are reasonably close.