Welcome to the Disney Parks Moms Panel, James!
I am so happy you are planning on taking advantage of all of the restaurants at Walt Disney World Resort hotels. As each of the hotels are so different, there is a huge variety of restaurants available of you are willing to "resort hop" between them. You can most definitely take advantage of
complimentary resort transportation to travel between Walt Disney World Resort hotels, including to hotels where you are not staying. When traveling from Disney's Caribbean Beach Resort, you will need to catch a resort bus to a theme park, water park or Downtown Disney to make a transfer to get to the resort where you will be dining. If you will be dining at Disney's Polynesian Village Resort, Disney's Contemporary Resort or Disney's Grand Floridan Resort & Spa, you should take the bus to Magic Kingdom and then use the resort monorail to get transportation to the hotel for your dinner. Otherwise, you can use bus transportation from your transfer park to your destination hotel. I recommend keeping an eye on park hours when selecting where you will transfer. When traveling between Walt Disney World Resort hotels for a reservation, I always allow two hours travel time to ensure I have plenty of time to account for waiting for the bus from my departure hotel and at the transfer point.
Please let us know if you have any additional questions as you prepare for your trip! T-T-F-N, ta ta for now!
~Crystal B.