Hello, Jason,
It sounds like you may be planning an epic land and sea adventure starting with a Disney cruise followed by exciting experiences in central Florida. When my family and I sailed on the Disney Treasure last year, we went straight from Port Canaveral to our land-based headquarters for a few days at Disney's Art of Animation Resort while we spent a full weekend at the theme parks of the Walt Disney World Resort. Later this year, we are reversing the order by starting at Disney World before we drive to Fort Lauderdale to cruise on the Disney Dream.
The cruise ship terminal at Port Canaveral is an amazing example of efficiency. I am astounded every time I watch the crews onboard and on land turn over a ship between cruise itineraries. On embarkation day, you will find plentiful seating to comfortably wait for your cruise to begin. However, on debarkation day, you'll notice the streamlined facility is designed to help disembarking Guests advance to their next destination quickly and efficiently. Since most Guests are more interested in moving along to their flight home or, perhaps, their flight to Pandora, there isn't a need for substantial seating areas after the customs area after disembarking from the ship.
In my experience, the rental car shuttle bus drivers are quite used to ferrying large parties along with their luggage to and from the rental car facilities. The fast pace of the cruise ship terminal can sometimes make one feel a bit rushed. Because of this, my recommendation would be to keep your party together and proceed to pick up your rental car together. That can help advance your vacation to the next phase as quickly and smoothly as possible.
Depending on the needs of members of a party, it may be helpful to consider an approach that is somewhat more laid-back. For example, you may opt for a Delayed Debarkation on the last day of your cruise. If you are considering having some members of your party wait a little longer onboard their Disney Cruise Line ship while others scout ahead to procure transportation at the car rental facility, be sure to inquire at the Guest Services Desk whether there might be a need to keep the group together still. Some examples might be related to ensuring minor children have a required parent or guardian or streamlining the escort protection of a party who made a high-value purchase onboard.
Tony's Tip: Whenever it becomes necessary or preferable to split up our party while on vacation, we find it helpful to designate "captains" over our separate groups. Each designated leader is in charge of holding the important travel documents and personal items for members of their respective group, including passports and other identification, medications, tickets, etc.
Jason, if you have more planning before you begin your Disney cruise, just "give a little whistle." Your pals here at planDisney are happy to offer any support we can.
Have a magical cruise, Jason!
~Tony