I kind of did everything backwards and ended up saving myself some $.
I booked the resort and the cruise separately. I did this for two reasons:
1. By booking separtely I landed the Fairytale Package that included room (7 nights) at the Caribbean Beach and four Ultimate Park HOpper passes during the length of our stay. I paid $1600 total for the seven nights "land."
2. The second reason I did it has to do with Disney's Transportation system. A friend of mine who cruised before me complained that the Disney folks didn't pick up from her resort until the afternoon and she wasn't on the ship until after 3 p.m. (they start embarking at noon). She didn't get a chance to do a whole lot of exploring before she had to get ready for the safety drill, Sail Away party and dinner. Too rushed.
I booked the cruise separately, without Disney's transfers or their insurance (I got mine cheaper through
AAA). Since we didn't want to be stuck waiting for Disney transportation during our land stay (we went in high season), we rented a car at a minimal cost. We drove to the Port ourselves and were on the ship enjoying by 12:15!! Our fellow resort guests didn't arrive until 2:30.....
PERSONALLY, I think you need at least 5 days to adequately enjoy the Disney Parks. By booking everything separately instead of a package, I saved $ and got a 10 night vacation for less than a 7-night Land/Sea! My
travel agent and I worked every option and this was the cheapest way to do it.