>>2796239
>I wouldn't mind doing a connecting flight
the only reason I mentioned it was because connecting flight typically don't fit a low budget
between islands you're looking at $200-350 p.P.

>Jamaica looks promising,
if you like music stay in Montego Bay and Negril
the food is also nice

but again not really that much culturally and historical to do, it doesn't compare to say central Europe or Japan / SK / China in any way
I'd do ~1,5weeks there then fly to next island (where ever you find a nice resort your gf enjoys)
explore a few days on your own, before your gf arrives

also if your gf (and you) like hiking
on most Caribbean island there are some (short, like 1-2h) hikes to really beautiful secluded beaches / waterfalls
which could be somewhat a compromise between doing "something" and rotting away on the beach

>Cuba maybe a bit trickier logistically.
which is a shame
because that's exactly the destination fitting your requirements

easily enough for 2 weeks traveling around, seeing Cuban history and culture stuff
and plenty of really nice resorts and beaches, even within / near cities so you can do something outside the resort

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I took three weeks in December off at the beginning of this year when I was single planning to go backpacking through South America. However I now…