Mosquito Repellent: You know what mosquitoes love? Tourists. When I moved back to Puerto Rico I was in denial and figured they'd get tired of me after a while but for a good two months I looked like I had chicken pox. They get worse during the summer and they will find you at the beach. Not to scare you but there is also a type of mosquito that carries a disease called dengue. Fever, nausea, being hospitalized aren't much of a vacation. In my 23 years of life here I've never had it but a quick pitstop by any of our many Walgreens-- do not buy souvenirs there, for God's sake, I don't care how colorful and plasticky they are-- to pick up a bottle of OFF will keep you dengue and itchiness free while you do whatever it is you do in the Caribbean.
Sunblock: I know, no shit. You want your money back. But if its your first time here you don't want to mess around with this sun, specially during the summer. This is particularly important if you're at the beach where our perfectly white sand will serve as a reflector. I've seen Puerto Ricans turn purple because of massive sunburn, to the point that they're peeling the skin off their ears. I know, I'm really doing a great job selling the Caribbean but again, while you're at Walgreens just grab a bottle of Coopertone waterproof. You'll still get a tan, I promise, our sun is that strong.
Passport: Even if you're going to a US territory, maybe you'll meet some really nice rich people that have a house on St. Croix or find a really cheap boat ride to the Dominican Republic. No passport? Oh well, guess you can't go. My brother worked as a gate agent for American Eagle in San Juan for years and there was always one guy who didn't have his passport and there goes island hopping to Jamaica.
Rent a car: Just because its an island doesn't mean its small. If you really want to immerse yourself in a place-- from our biggest Antilles Cuba to a spec of land like Culebra off the coast of Fajardo, PR-- give yourself mobility. Cabs are expensive and cabdrivers are lazy so they won't take you deep into the mountains or to the other side of the island. A GPS is an added bonus but basic map reading skills should get your around fine.
Make friends: This is surprisingly easy to do around here where even at the doctor's office the lady next to you will start talking to you and tell you her life story. Moreso at a bar or gallery or restaurant or dive shops. Just smile, say hi, and ask questions, have a few stories ready, and make it a point to express how much you're enjoying being on the island. The best people to talk to are bartenders, dive masters, and inn-keepers in beachside towns like Rincón or Cruz Bay, many of which are displaced Americans who decided to hell with the US and came down to Caribbean to live. Those always have great stories.
Vegetarians: Good luck. Just so you know, the rice and beans has ham in it. Your best bet may be to get a vacation rental or campground with a grill and cook yourself. Its not impossible to find good vegetarian fare-- specially in Puerto Rico-- but in some of the smaller islands it can be a challenge.
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