I just read through all 46 pages of this thread! I am seriously contemplating OBB this cruise for DS and me when we are on the Magic this summer. DS will turn 8 on Oct 11 (2014) and should have fall break at his school during this week.
This summer will be DS's first and mine and DH's second cruise (first was RC for a wedding). We are doing the Med cruise to Greece in July! So getting organized for that is taking lots of my time right now. And the boys are going to Colombia next week for 10 days so I have to get DS packed up for that trip as well. We picked the Med because DS wanted to go on a boat, DH said we should do Disney, right? and I didn't like the options for the Eastern or Western or Bahamas. That left Alaska and the Med.

Spoiled little guy

...Disney, South American and Med cruise for the summer...plus a week with grandparents which should include a day or two at the beach.
I grew up in FL so have spent a fair amt of time in the parks over the year (first trip was in mid 70s)...DS's first trip was for his 4th birthday and in 2 1/2 years he has now been 6 times! LOL! We got annual passes last Oct so I've made a few excuses to go...DH had to go for work, Star Wars Weekend, etc....going to do ToT run in the fall. We live in ATL so not too bad to get down there either driving or flying.
Hoping to make this work out!