Lorna,
Thanks for your question! I always love the ones about dining at Walt Disney World!
To begin with, I think you will love staying at
Disney's Caribbean Beach Resort. For my family the addition of the
Disney Skyliner is a game changer. We love it when the transportation from the resorts to the parks (two in this case) is an attraction unto itself.
To your question, Disney has suspended
Disney Dining Plans for the time being, as you can read on this post at the
Disney Parks Blog. So the likelihood in August of either a free Disney Dining Plan, or one you pay for, is unlikely. I will also note that with the Dining Plan promotions of the past, the ability to upgrade, or the availability of certain promotions at specific resorts, changes every time. So at this time there is no way to know for sure.
My advice would be to expect that you will not have a Disney Dining Plan available for an August vacation this time around. If, however, Disney does re-start the Disney Dining Plan promotions, make sure you check any stipulations that they put on the program, especially as it relates to upgrading and at which resorts the program will be applied. When those plans come out, ask us again at the panel, as we will be able to help you think through options.
Until then, you might want to do what my family is doing these days, to get ourselves excited about our upcoming trip. We are voting on our top 3 restaurants per park that we want to try out when we return, with a focus on ones we have never been to, or have not been to in several years. With a mix of table service and counter service venues in each park on our list, we can get excited about what we will try out there, and still have the flexibility to dine without having to make a ton of reservations.
Have a Magical (and delicious) Vacation!
Doug