Twice in my life, I have ventured into the realm of a "relationship" with providers. It was still business, in that cash was paid for sex, but there was genuine affection both ways. In either case, there were times I would have been more than happy to have them come on a vacations with me, and I suspect that they would have done so at a pretty reasonable rate. The one SP I saw, only charged me for "naked time" as she put it. We would usually go for dinner, maybe even a movie, then back to her place. On the way out, I would pay for the hour or two of sack time. A couple of times, I fell asleep, spent the night and left in the morning, and still paid for just an hour or two.
However... both of these girls were to some extent, bat-shit crazy and the odd time, would demonstrate this with great flair.
I'm pretty sure that having this happen mid week on a tiny island someplace would bring "awkward" to a whole new level! Personally, I don't think I'd ever want to head away with anyone, SP or otherwise, that I didn't know very well...
If you are serious about this, apart from the long sessions suggested above, I might be inclined to try a weekend together or something.
Besides, it's nice to "Shop Local"!