As mentioned before Old San Juan(here are some images of this lovely town: http://joeastacio.zenfolio.com/p267725242), El Yunque rainforest, Ponce has an interesting historical landmark at the town plaza, cathedral and fire station that date back to the 1800's... And must try Rosa de Triana's paellas at old San Juan, close by the cathedral :]
We've gone there a few times and I really enjoyed Old San Juan. There are many architectual opps and many festivals that happen if you want to shoot that type of thing. Sunday's are kite flying days down at the fort if you are there over the weekend. Don't try driving in old San Juan though, just walk. Rain forest is also nice and plenty of beaches to shoot also. Just depends on the subjects you like.
The fort in San Juan is nice, phosphorescent bay, el yunque...bring a macro for coquis, all of the towns have central squares which are really cool, paso fino horses are common to see, aricebo observatory, a mahogany forest at Guajataka if you're a Scout, chicken fights if you're into that, the Southwest section has a desert park...I can't remember the name.
One can snorkel year round and it's like being in a warm bathtub full of the fish you see in petland, if you have some underwater gear then things could be nice.
I loved Puerto Rico, we were stationed there for 4 years. Nearly every street will have something to photograph. The culture is rich, the people are friendly, and everyone speaks english (if they want too).
Hi! I live in San Juan. Check out my smugmug puerto rico galleries (links below). Depending on what you want to shoot I can recommend a bunch of places can gan give you tips on each one.
Generally the light here is extremely contrasty so I would bring hard split ND and ND grad filters. Its not as bad this time of year though but I would still bring them and a polarizer.
You can use a tripod almost anywhere so I would bring one too. Its hot and humid here and the old city is quite hilly so keep it light and of course the rainforest is extremely humid and the terrain very steep. Bring rain protection.
Rain protection is a great reminder! It can rain at any time in the Carribean. We're visiting again in January, but don't get much time in Puerto Rico. I'll have to check out the links also. I've never brought a tripod along, but planning to this time to shoot a bit more video. I've got some of my shots on facebook and on my website so PM me if you are interested.
Last time I visited Puerto Rica I stayed at the Casa Cubay Ecolodge/B&B. This is a quaint spot on the border of El Yunque Rainforest. You can access and hike the rainforest and various waterfall pool right from the property. This area is far away from the main entrance to El Yunque and is frequented by locals instead of tourists. In addition, you are only 30 minutes from the coast where you can do a night kayak trip through a bio-bay where bioluminescent dinoflagellates create an luminescent trail as you paddle or swim.
get over to giligans island if you can. Me and my girlfriend stayed in San Juan, but had a car so we made the trip over. Its one of the most beautiful places I have been to.
I dont think you will see any tourist there. Also check out the luminescent bay, and do it at sunset. http://www.flickr.com/photos/mstallone/6852447745/in/photostream