I used to have that "gig" in the Caribbean, I lived in Miami, and about once a week my day started at the airport, flying a puddle jumper (but sometimes a jet to the more popular places) to some island, usually in the Bahamas or Jamaica, but often as far as Aruba or Bonaire, and sometimes to mainland So. America. I filled up my passport, and got 10 extra pages and almost filled them up.
Everyone else thought it was a great job, but it was still work everyday, it was never like hanging out at the beach.
I still say there is NOTHING in my house that looks like a hotel, except the towels and ashtrays from a bunch of famous and fancy places.