San Juan, Puerto Rico

I have been to San Juan a few times, but not since the last hurricane. Some friends rented a jeep and drove out into the countryside and really enjoyed stopping at some small, authentic “mom & pop” restaurants and had great food and friendly experiences - recommend doing your research first though. Highly recommend the empanadas - SO good! I also really like Old Town.

Big fan of San Juan. As the others have suggested, there are a lot of big name hotels in the Condado Beach area; the Caribe Hilton, Vanderbilt Condado, Marriott are a few. Depending on how long you have, I'd recommend a day in Old San Juan to see the two castles - Castillo San Felipe del Morro and Castillo San Cristóbal. Depending on the level of physical activity, I'd HIGHLY recommend visiting El Yunque (the rainforest), however, this can be a mildly strenuous hike.