Muelle Barón, Valparaíso * video paddled near the coast until Viña del Mar where waves began Downwindfun
Playa Topocalma, Puertecillo, Matanzas, La Boca
wind the prevailing wind is SSW so you can start at one of the south launches and head NE along the coast, but carefully scout the beach breaks and if/when you can get through them going out and coming in.
Surf
Maitencillo very popular for surfers and surf schools, you will have to determine which surf breaks (if any) are good for surfskis