Hey Howdy Hey Kate and welcome to planDisney!
I am so excited for you to have the experience of visiting the Most Magical Place on Earth during the most magical time of the year! Best of all, you will be able to welcome in the New Year with a celebration that will surely be something Magical to remember! Now it sounds like we just need to work out the minor details of where you will be staying. Let's review a few things so you have all the information you need going forward.
Starting your vacation at one resort and then moving to another, split stays as we like to call them, have many benefits. Being able to check out two separate resorts and enjoying all they have to offer gives you a different glimpse of
Disney Resort Collection amenities. Every resort is themed differently and has a lot of familiar favorites that they all share, but some unique takes on things specialized for that resort, like dining offerings and pool options. When you check-out at your first resort and are moving to the next, let Disney do the heavy lifting! You can take your luggage over to Bell Services and they will transport your luggage over to your new resort.
Considering the dates your will be traveling to Walt Disney World, that time of year is usually a really popular time to visit. If I were you, I would book whatever you can for the first couple of days. You can always keep checking after you have a secured booking to see if anything does open up for the full stay at Disney's Caribbean Beach Resort. This is super easy to do from your
My Disney Experience account. Once you have your reservation linked to your account, scroll to the "My Plans Reservations and Tickets" section. Look on the far right where you should see "change/modify reservation" and you can go through and check on availability at the Caribbean Beach Resort. If you do end up finding a room after your initial booking, make sure to change this through your My Disney Experience account and then give Disney a call and ask to have both of the reservations combined so you won't have to change rooms at the same resort.
Where this might get a little crazy is with your theme park tickets. On your first reservation, you may only be able to book a couple of days in the parks and then a few days with your second reservation. Totally fine to do this have two separate vacation packages with resort room and park tickets. You could also book them separately with room separate from tickets so you can book all the tickets at once which will give you a bit of saving on the per day cost compared to say a 2-day ticket and then a 3-day ticket.
Long story longer, book what you can now and modify your reservation as you get closer and hopefully availability opens up. If not, you have a grand opportunity to take advantage of a split stay! Hopefully, this helped get a plan together. Please feel free to stop back and let us know if you have any further questions as you continue to plan for your Magical vacation, we would be happy to help!
Have a Magical Day,
Nick