We like getting to the port early, as we like to have lunch on board in the open MDR, get rainforest room passes, verify dining arrangements, and possibly sign up for some special events. Because some of those things are time-limited in terms of when you can do them, we prefer arriving as early as possible.
In the past we have had
DCL pick us up at our resort, but we found we didn't have enough time to get what we wanted/needed done on board that first day.
We have used a private towncar service, but had two issues: one is cost, as there is only two of us; the other is that they could not pick us up earlier than 1030 and that still got us to port a bit later than we prefered (it was a bit of a rush).
Our last cruise we found a solution that we think works for us:
Arrive 3 days before cruise (we cruise in the winter and live in Canada; 3 days in advance means I literally could drive down if we had to due to flight cancelations). Spend 2 nights at WDW resort of our choice. Day before the cruise, in the late afternoon or evening, take DME back to the airport (DME allows this, and we discovered you do NOT need a "fake flight", just tell them what time you want to be leaving your resort/arriving at the airport and they will fit you in according on a scheduled bus close to your time (eg. you may want to leave at 4pm but the bus will be at your resort at 330, so you will be put onto that bus -- you need to have some flexibility). Then spend the night at the Hyatt inside the airport. In the morning, checked bags inside by the room door by 8 am for pickup. Head down to the DCL transfer desk and get in line and eventually get on the bus and to the port.
For us, the Hyatt was great because the rate we had included breakfast in their Hemisphere's restaurant, and that breakfast starts early (about 6 am if I recall) (also, the Hyatt was cheaper than the Disney resort we had been at the previous two nights). So, we got up, got ready, had an early breakfast and were back in our room in time for the luggage pickup at 8. We then leisurely finished getting ready and then headed down to the DCL transfer area. We joined the line. We were one of the first people on the second bus that left the airport. we got to the port nice and early and after getting checked in had time to explore the port and sit and relax -- not rushed like we were and felt when the car service had dropped us off the previous cruise. We had an early boarding number and were on the ship with plenty of time to do everything we wanted to get done in those first few hours. Again, not rushed. Had time to relax and enjoy lunch, etc.
One change we will make for next time: go back to the airport later. We went later afternoon, thinking we would have dinner at the airport and use the hotel pool. We did have dinner at the airport, but did not swim because the air temp was rather cool that evening. For our next cruise we will have dinner at a WDW restuarant at our resort (an "early dinner") and then head to the airport after that, in the early evening. Enough time to relax at the Hyatt and get ready for the cruise the next day.
This will not work for everyone, and some people definitely won't like the switching of hotels and such. It works for us, though.
SW