I don’t remember seeing an email about this or I may have missed it but it looks like San Juan Puerto Rico can now be booked with points on the Southwest site which also means you can also use your companion pass as well. Previously, this destination was only bookable on Airtran but they are slowly bringing over their Mexico and Caribbean destinations. I can’t wait until they add Cancun because I want to go back! I did a sample ititinerary of early Sept and the points redemption amount seems reasonable. So start booking!