Old San Juan, Puerto Rico
I was in San Juan, Puerto Rico a couple of summers ago and I really enjoyed the beautiful buildings in Old San Juan. I wasn’t staying there, I was about 15 minutes east right on the beach. Old San Juan is accessible by public bus but the bus system isn’t reliable so I wouldn’t count on that. I was there with my family and we rented cars which was a great way to see the city.
Been to San Juan and Santo Domingo in the Dominican Republic which is the oldest city in the Americas. The people in both cities are extremely friendly.