You don't see Puerto Rico on the lists of common tourist destinations---and therein is hidden its beauty. The island is an autonomous U.S. territory. Indeed, while in terms of culture it is definitely a U.S. territory, it is also very clearly autonomous. The people are... well, different---merrier and more relaxed. You can see cops on the street chatting with civilians. People fry snacks on the street and sell them (rather greasy snacks I agree---but that is another story).
It is best to visit Puerto Rico outside of the hurricane season which lasts from June to November. We decided to take the small risk and went there in early September. The weather was quite enjoyable: even though it rained a little, it was always warm and we had many opportunities to enjoy the beach.
Priority number one was to explore Old San Juan. We could easily walk around it in a day. There are numerous small squares that we saw, and we found the most interesting ones listed in many tourist brochures. We spent some time at the Spanish fortifications with the famous sentry towers (it seems like these are present with slight variations in other places around the world---like Malta).
We could almost drive around the island in one day. We decided to skip the Arecibo observatory (world's biggest radiotelescope), because we wanted to get a feel for how real Puerto Ricans live. We stopped at small towns here and there, and our impression was that the countryside is poor, but has a very distinct and gentle soul.
Ponce, the big town in the south of Puerto Rico, is touted as an attraction in many brochures, however we didn't find there much of interest. The fire station is certainly quaint and amusing, but we dare to say that it is not quite worth the trip. Still, Ponce was a part of Puerto Rico that we wanted to see and experience. There wasn't much to do there: we walked around, stopped at a church, then headed back to San Juan.
We really wish we had seen Culebra---the small island to the east. Because it was a holiday, we were advised against taking the ferry, and a plane ride from San Juan would have been too "commercial" for our tastes. On another visit to Puerto Rico we will definitely want to visit Culebra.
The international airport at the capital is big: major airlines have regular flights between the continental U.S. and San Juan.
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