Seriously do what I said. Sign up for some online dating site with Mexican or Columbian or whatever country girls looking for a foreign Prince to come save them. I would say Cuban but I don't think they are online.Funny, I started this thread like 10 months ago. I actually won't be taking the vacation now until feb. I'm still thinking Havana or maybe that blackbeard place mentioned above.
Chat up a few. When you have a few you really think it would be fun to visit, go.
Fuck those resorts with hookers. Meet some real girls. Or girl. You will have the time of your life. She will probably even cook dinner for you and you'll get into the local party scene.
If she doesn't work out it's not like it's hard to find paid help in those places.
Yeah you probably need to learn a little Spanish too, but not much. And to me that cultural immersion is the whole reason to travel. A single western guy can pick up in any of those places and with the internet these days you will have her name and number before you book the ticket.