The logistics are a bit challenging but doable...
1) Carry-on is required for cruise and flights so no bag checks and TSA-Pre status so you have short security lines.
2) Arrive in Florida from California on Wednesday 1/6/16 taking first flight out so you arrive by 4pm and take car to WWoS Expo to get Dopey packet pickup.
3) Enjoy Dopey and the parks for 4 days.
4) Car to Port Canaveral on Monday, 1/11/16 to arrive by noon - check in at Gold desk (6th cruise on
DCL) and board ship - first time on Dream (rest were Magic and Wonder trips).
5) Register immediately for
Castaway Cay normal run planned for 9:30am on Wednesday 1/13/16 - the Castaway Cay Challenge is run 1.5 hours earlier so you can run on the island twice to get a 10k (5k + 5k) run in.
6) Use express disembark on Friday 1/15/16 to leave ship with carry-on bags at 8am.
7) Car to MCO by 9:15. Carry-on and TSA-Pre again.
8) Catch flight from MCO to SNA (or LAX) - there are several options that leave between 10am and noon and arrive between 3 and 5pm.
9) Taxi to Expo by 5-6pm (we'll get there at 5pm)
10) Pick up Rebel Challenge packet and enjoy DLR Expo for an hour.
11) Enjoy Rebel Challenge and Parks for 3 days.
12) Head home with bling and then pass out.
Key things to remember - book flights and cruise first before races. If Annual pass or DVC, use early race registration option. Castaway Challenge requires cruise booking confirmation number.