8. Old San Juan
Encompassed by old colonial buildings, cobblestone streets and forts, Old San Juan is one of the largest tourist areas on the island, and with shops, some great dining and a lot of history. Old San Juan (technically not a city) has a constant police presence, but can be congested.
If you’re looking for a place that’s convenient to all the amenities and allows you to connect with all sorts of people, Old San Juan is the area to explore.