MAtt - people have had great times in Cuba. But, since no Cuban National can enter a hotel you really need language skills to make arrangements. But, with google - OK maybe. Argentina, I loved it and there are clubs . BUt, VENEZUELA??? I used to go there several times a year and it was wonderful but it is imploding, very dangerous, scare food. I would most urgently caution against this.
Besides. Francois point is well taken. The man will be 10,000 miles away.