Colorful facades, welcoming plazas, and centuries of history make Old San Juan a fascinating place to explore on foot. Walk its cobblestone streets with a guide who shares the stories behind the sights. You follow the painted facades through plazas and side streets while your guide lays out five centuries of Puerto Rican history building by building. Your route brings you to Castillo San Cristobal, among the largest forts Spain built anywhere in the Americas, where the scale of the walls makes the city’s strategic value obvious at a glance. With every stop, you’ll get to know the city beyond its postcard views.