The Bay Mouth (El Boquerón) opens out into Gulf of Mexico at La Boca del Perro (guarded on the east by La Piedra del Perro and on the west by Fortín de San Jerónimo del Boquerón) is a safer place to practice catching waves headed onshore video, video 2, - the waves are filtered at the opening and kind of lined up past the entrance.
There used to be a 22 mile downwind race from Culebra Island to Fajardo. As far as we can tell it hasn't been run for some time. Harry Negron at Ozone Puerto Rico was involved. You might check with him about any future race possibilities?