With a great mix of resort-centered activities and off-site experiences, a Puerto Rico vacation has the best of all worlds to enjoy as a family. Tour the fort in Old San Juan, admire the rainforest from observation decks, dance to the local music and ride a trolley through an extensive network of kid-friendly caves 200 feet below ground. But do leave time to experience the amenities found at the numerous resorts here. Families with younger children will want to book a property with kid-friendly beaches and gentle water on the Caribbean side; those with older children might appreciate the bigger waves on the Atlantic side.