Hi April,
Using Disney's complimentary transportation when staying at Disney's Caribbean Beach Resort is fairly straightforward as you will need to catch a bus from your Resort hotel to each of the four theme parks, two water parks and Downtown Disney.
Things start to get a little tricky when you want to travel to another Disney Resort hotel as this means that you have to go via one of the theme parks, water parks or Downtown Disney.
If you are wanting to plan ahead, there is a fantastic transportation wizard tool which I like to use available at www.ourlaughingplace.com.
It allows you to enter where you will be travelling to and from within Walt Disney World and then provides details on the best route(s) to take as well as giving an indication of the amount of time that the journey will take. I would add an extra 20 minutes onto each estimated time to allow for the time which may be spent waiting for your designated mode of transport to arrive.
I hope that this information has been of help and wish you a magical trip filled with memories which will last a lifetime!