Same as always. If you do visit make sure to email me. Ill take you out to a nice dinner.

Do you have any recommendations for first-time visitors? Apart from Culebra we have no idea what we want to see.

Absolutely. Go to the west side to Cabo Rojo. Eat some great fresh seafood. Then head to Lajas (15 min drive) at night to see the bioluminiscent bay (wear jeans and bring mosquito repelent). Then go to the east side and end up in Fajardo. Visit El Yunque and then eat some local delicacies in los kioskos. After all that, call me, and Ill take you to my dads hacienda where Ill serve some rice and beans while you relax in a hammock and look at El Yunque from a distance.

How much Spanish should I try and pick up? Will it help?

If you love to travel, you should pick up as much Spanish as you possibly can! The best analogy I can think of is that it's like learning to scuba dive - it grants you access to a whole new fantastic world that you previously could only spectate on TV. Latin America is huge and diverse and wonderful (for that matter, Spain is pretty awesome too).

In touristy areas you'll be fine.

Most people will be able to understand you. If not, you'll figure it out quick by their expression and you can adjust your words/speed.

While we have local music/tv, most of the media is from the US. We are taught both languages from kindergarten, but like everywhere, some schools are better than others.

None. You'll do fine. Just get used to being called a gringo (slang for american).

Sounds good!