I just checked old emails from years past. Our 2 most recent trips to Jamaica I found the best prices at 75 and 82 days from travel respectively. My best advice is to check prices daily and be ready to jump when you see a price you can live with. Like sammyb said, if you book with Southwest and find a lower price later, they will refund the difference or give you a credit for the difference depending on with price category you purchase. If it is the "wanna get away" price, the best they will do is give you a credit for your next flight within a year for the difference. Hope that helps.
