The lady has to already want to be on vacation where you are.
When I travel to a place so a gentleman can see me, I am usually only in town because he wants me there. Now I maybe be able to see other clients while there, but that requires $$$ for advertising, but nothing is guaranteed.
Some ladies may love the idea of this deal, but vacation to me means with friends/family in a locale of my choosing. I wouldn't really be able to travel with anyone as I would have to abandon them at night.
"I am flattered when called beautiful. Even more so when called dangerous." ~ Vanica Love