According to U.S. News Travel the best time to visit Puerto Rico..."The best time to visit Puerto Rico is from mid-April to June, right after the busy winter season and just before the rainy summer. Spring weather is also very pleasant, barely escaping the mid-80s on most days. The island sees its best weather in winter — which is partly why this is the most crowded and expensive time to visit — but with careful planning you might uncover a pretty good discount during those months as well. You could also plan an enjoyable and affordable trip for the fall, when hotels can be as cheap as $80 a night