It totally, completely depends on what you want. I should save this post somewhere as I explain it so often (hee hee). If you book the land/sea package, you have the convenience of one booking and the whole thing is done....no thinking, very little decision making. WHat you will frequently lose is some money.
There are only a few ways to save money on the cruise--you can book thru a discount agent, and you can have a coupon code for an onboard credit. You can sail in value season. Personally, we LOVE September as the weather is warm but not opressively hot, and the crowds are gone, the prices are the lowest they go.
There are LOTS of ways to save $ at WDW. First, the resorts frequently run specials. Check mousesavers.com to see current specials. Secondly (this is the biggest savings I know of), the land/sea package includes the Unlimited Park Hopper passes. These passes are based on the length of your stay, and include admission to everything on every day. Will you use the water parks, pleasure island, wide world of sports, etc? Will you go to a park on the day you arrive AND on the morning you leave for the ship? If the answer to any of these is no, you can save money by purchasing Park Hopper Plus passes. You can buy these ahead of time at any
Disney Store or on line at the WDW site.
Park Hopper Plus passes are based on the number of days you want, but unused days never run out...so if you don't use them, you can save them for the next trip. For our family....if I fly in, we arrive at WDW at about 3 pm. I'd like to get there earlier, but with plane times, etc. Mears to WDW,etc. I know that 3 is reasonable, which means 3:30 to our room. We then hit the pool, and do a character dinner (usually at Chef Mickey's, but 1901 Park Fare is another option). That way. DD has had the Disney Character experience but we haven't spent a lot of $ on park admission for a few hours. On the day we leave for the cruise, we usually do a character breakfast at one of the resorts--Cape May Cafe is a good one. Again, no park admission. If we were to go to the parks, we'd need to transport to the park (WDW says to allow 40 minutes, but it really doesn't take that long)...so I'd get to the park at the 4-4:30 range and an hour later have little people wanting dinner...no park time!
So...a character meal for a child is about $10, for an adult it is about $15. Dinner is about $23-25 for an adult, again about $10 for the kids. The UPH passes are based on about $40 for kids, $50 for adults per day (you can check the exact prices for your length of stay at the WDW site.)
I figure if I don't go to a park, I save $50 per adult per day...so if I spend $15 on a breakfast, I've saved $35. Park admission for a full day is a good value. However, for a few hours, it's pricey.Park hopper plus passes do give you admission to the water parks and /or pleasure island (they are called extra features or something like that), but they are limited in number or times while the UPH are unlimited.
Another way to save $ at WDW is that each category on the ship is tied to a particular level of resort at WDW. You may not want the category that goes with your cabin. For instance, you may want a verandah on the ship, but be happy with a value resort....or you may have a category 6 on the ship but want a concierge level room at your resort. Ok, if you want a lower level resort than is tied to your cabin, you can save major $. If you want a higher level, booking separately gives you that option.
We've stayed at the All Star (value level resort) and at several of the Deluxe level resorts (Animal Kingdom Lodge, Poly, Old Key West, etc.) Quite frankly, we found the attraction of the animals at AKL to be wonderful. I wasn't overly thrilled with the things at the Poly or Contemp. The rooms are a little bigger (how much time do you spend in your room at WDW)?...but otherwise, I didn't find them to be worth triple the price of a value resort.
Again, it all depends on the decisions you make...but you can save very serious money at WDW by changing your resort level and by changing the type of passes you have--with very little impact on the fun of the trip.
With 4 people, a private car service (Happy limo, FL limo, Tiffany limo are some) will be cheaper than
DCL transfers. In addition, the limo service will run when YOU want it to rather than on their schedule, and will allow you a 15 minute stop at a grocery or wal-mart on the way to the port. A much nicer situation.
If you use DCL transfers and stay at a resort that isn't designated as a cruise resort, the bellman will take you to the nearest cruise resort to catch the DCL bus.
If you do
trip insurance and book separately, you will need to use a private company to insure the whole trip. DCL willl only insure the part that you book thru them. The good news is that private companies are cheaper.
HAppy planning! Have fun!
also -- I didn't like that we paid for park tickets for all day Sunday, the day we left for embarktion. That probably factors into the "wish I realized that before I left" and the cost savings the smart ones understand.
Thanks.
I really did try to work it out several times and several different ways b/c I read it's cheaper to book it seperately but again no dice!! If I wanted to stay Value and go with any level of stateroom or even a mod I could possibly see a savings but not booking the Poly or BC at $280 or more a night. The price I got seems pretty good to me 
