My aunt is a travel agent on the side, she books all my parents (and my dad's siblings) vacations and always knows the best deal. We chose the time we did because it works with both our schedules and our families. Kory and I are staying ten days, and his family can only make it the first seven days, and then my family can only make it the last seven days, and then we have family and friends doing shorter 4 day stays. So group discounts didn't really seem to work for us. But my aunt is keeping an eye on when the charters come out and she says its usually the end of May to sometime in July where she's found the best prices for December. So we are waiting. I'd be a bit more nervous, but we did this for my sisters wedding a year and half ago in Jamaica, and all worked out well!