Okay not the same country but the same region - Caribbean.
I can get return economy flights for £150 each. So it makes travelling a lot more affordable. I absolutely love the tropical vibe of the Caribbean, and the flights are relatively short for that feel - only 8 or so hours. Easy enough time difference too.
We went to St Lucia in January and had a great time. We are about to go to Italy for our summer holiday. I want to squeeze in another trip in late November and I can get Caribbean flights to Antigua or Tobago.
DH groans that he doesn't want to go to the Caribbean again so soon. Is it dumb to do repeat visits to a region? Every island is different!