Man, just go to Puerto Rico! You don't even need a passport if you're a US citizen. You don't have to exchange your money because they use US dollars. You can use your cell phone there AND a lot more people than other countries know English b/c it's a US territory.
It's kind of a cheap vacation if you do it right too. The women there are breathtakingly beautiful, the people are friendly and take pride in their island and teaching others about it. The food is AMAZING. There is great shopping and nightlife of course is JUMPING, sooo much to do. Plus SO many historic sights, especially in Old San Juan which is said to be one of the oldest cities in the western hemisphere and so much of it is still preserved from the streets to the forts. There's a rainforest (El Yunque) and SO many gorgeous beaches (esp if you go to the island of Culebra off the East coast, Flamenco beach was voted one of the best beaches in the world by the Travel Channel and others). I mean anything you want you got it there. I have traveled a bit and it's still my favorite place in the world. I am a little biased but everyone I know who goes falls in love and goes back.
Oh yeah plus is VERY safe for tourists to roam free, unlike places like DR and Jamaica. There is a lot of crime in PR but they do NOT mess with tourists. You can rent a car and do your own thing, it's easy to find your way around. Also I recommend renting an apartment rather than a hotel because it's cheaper and you get the real feel for the neighborhoods like a local. Like I said its safe to do, in other places in the Caribbean you can't really do stuff like that unless you know someone or something.
