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The two places in Puerto Rico I've run are through the southern town of Ponce and in the rainforest in the north called El Yunque. Then best place in Ponce is to start and end in the Plaza Mayor (town square). Ponce style is late 19th with marble-bordered sidewalks, gas lamps, painted trolleys, and horse-drawn carriages. Many streets are lined with wrought-iron balconies similar to the New Orleans's French Quarter. In El Yunque, the best place is to park you car in one of the tourist parking lots and run on the roads. When the day became too hot we would ride one of the natural slides, off the side of the road, into a pool of water (not sure if they still allow people to do that).