Cuba

Cuba is a beautiful country but it has several "problems" that will probably make going there not worth it for most single men on a short trip.

US nationals can not ordinarily travel to Cuba, and have to fly through Mexico, Canada, etc. to get to Cuba. That in itself is a big hassle.

The main problems with Cuba are the government near-monopoly on all tourist infrastructure and the two-tier foreigner/local pricing structure. Government monopoly on tourist infrastructure means hotels and even restaurants will generally be more expensive than elsewhere in Latin America. Air Cubana, all hotels, all restaurants, bars, shops, tours etc. – the tourists are up against a monopoly, and therefore all the prices are inflated, and non-competitive. Two-tier structure means that foreigners pay a lot more than local for the same things.

High-priced tourist infrastructure creates barriers between you and local women. For example, say you want to go out to a music bar in Havana. In any other country described on this site you can find music bars everywhere and they are filled with local women. In Cuba you have to look for non-touristy bars really hard. On weekends there are some "secret" places where the entrance fee is less than 5 pesos and everybody can afford to go there. All other places are filled with tourists, jineteros (young local men who make good money by trading with tourists), and prostitutes.

Another problem with Cuba is that you'll be hustled for money from locals a lot more that just about anywhere else in Latin America. Any time you relax and speak to a Cuban on a street or in a bar, he immediately tries to think of ways to can get some money out of you.

Cuba was one of the top prostitution destinations in the 90s. Since then Castro has been trying to make meeting prostitutes more difficult, but he also made meeting regular Cuban women more difficult along the way.

Cuba may be a great place to go if you want to live like a local for a while. But you have to live completely outside the official tourist infrastructure. You'll have to rent a room from a local and pretty much live your life like locals do (there is not a whole lot to do anyway). It could be an interesting experience for the right person and could be a great way to learn Spanish quickly. You'll also undoubtedly meet plenty of women if you do that.