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What are you ultimately looking for? If you want to be surrounded by the charm of Old San Juan and have walking access to the shops, restaurants, and historic sights then stay there. I've stayed in the El Convento Hotel. It's nice and tasteful but the rooms are smaller if that's an issue for you. Definitely check out the bar/restaurant called La Factoria.
If you want more of a resort experience and the amenities that come with that then stay in Condado or Isla Verde. The traffic around Condado can be a hassle especially on the weekends although it is season specific.
Make sure you rent a car and head to Guavate. They have some of the best lechoneras on the island.
Enjoy!
Welcome to PR! I recommended staying by the beach - Condado beach is the nicest. Then drive into Old San Juan. FYI, August is very hot and the sun is super strong. Don’t lay out in the sun, and make sure to stay hydrated/use sunscreen. I highly recommend seeing the Bacardi factory, El Yunque (rain forest) and the bioluminescent bay!
@BA1 I don’t know any Puerto Rican who would advise a tourist to skip out on the natural beauty and charm on the island to stay at a “resort”.
Condado! I'd prefer to stay in your Beach, because when you get out of beach you would like to go straight to your hotel. However, if you are going to the city you don't really care if you have to take a longer trip to get to the city. So I would stay in either Isla Verde or Condado
If you do stay in town stay up by the fort. Much quieter.
From PR, stay at a resort lol