We stayed at La Concha in Condado for a couple nights before our Merrytime cruise. Had a great time on the beach and also made use of their great pools. The location was good too - maybe a ten minute drive into Old San Juan. The only thing we didn't like was the poor quality of the pull out couches. We ended up sleeping three sisters to a king bed because none of us would sleep on it! Didn't really bother us and we loved the rest of the resort (and room).
Food was a big focus for us on our short visit. We had dinner at José Enrique the first night (walked from the hotel). It was awesome. This restaurant and its owner played a big role in José Andrés' book We Fed an Island about the Hurricane Maria recovery. Was fun (and delicious) to taste the food in person. On a coworker's recommendation, we also tried Raíces in Old San Juan. This was a little more touristy, but the food was still yummy (we all ate mofongo - a must).
We did an Old San Juan Walk & Taste tour through Spoon Food Tours as well. One restaurant we stopped at that I remember was Deaverdura. We also had popsicles at Sr. Paleta and liked them so much we got them a second time at the location across from our hotel.
Honestly, the food in PR is so good. Have fun, ask around and get the opinions of locals. You'll find the best spots!