This is a good question and I'll share my perspective. We started taking our kids to WDW in 1993 when they were 6 and 8 (now 21 and 20 - expensive college students!). We saved hard for our first trip but were still astounded by the "bottom line". However, we all enjoyed it so much, I set a goal to figure out how to do WDW on the cheap. BTW, our first trip we drove (cost savings .. haven't driven since and we live in the midwest). After a few more financially successful trips, we expanded to
DCL cruises. They are not cheap - better financial values can be had with other cruise lines (which we do also), but NONE have the "magic" of DCL. We have 2 2008 DCL cruises booked. I'll limit my comments to cruising DCL.
Once WDW websites, such as this, started there was a wealth of information from which to research and learn. Do your homework. Also, I'd suggest one big thing: determine your mindset going in. Many feel this is a 'once in a lifetime' so they spend on everything - excursions, spa, souveniors, etc. We settled early on with a mindset of: We want to go on many cruises. Thus, we can't afford to 'live it up' on every (or any) cruise, if we want to go again.
Others here have shared some of the strategies and I'll build on those: Go off season. This usually helps with aifare, too. Study the specific cruise date prices - usually you'll find cheap rates in September and early December. Book early and book on ship if you can (usually a DCL discount that can't be acquired anywhere else.) Then transfer that booking to a Disney specialist TA (such as
Dreams Unlimited) or just start with a TA (if no onboard booking) a that will 'monitor' the cruise rates to watch for a rate decrease so they can apply that decrease to you (DU once saved our family of 4 over $1200 with a DCL rate drop - since we had this money already set aside, we used the saving to upgrade to a verandah/balcony room - see below).
Rarely does DCL "discount" their cruises - early bookings are the best rates and more savings can be had thru a TA who offers you an "on board ship credit". Consider a Disney Visa credit card (always pay off monthly!). We use it for major purchases and then use the "reward points" to pay our purchases onboard. For our 2008 Panama Canal cruise we booked on Disney's website ($25 OBC) with our Disney Visa card (getting a $50 OBC for using it) within 30 minutes of that cruise being open for bookings. This is a 'hot' DCL cruise - most aren't - and by late afternoon our specific cabin category was $1200+ more than what we got it for at opening bell. Then we transferred to Dreams Unlimited and got a $200 OBC. Every dollar helps.
Speaking of cabin category. We've had the cheapest inside stateroom and we've had large balcony rooms. However, we are just as happy with the cheap inside staterooms. The Panama Canal cruise, all 15 days, will find us in the cheapest inside stateroom and thrilled to be on board!!! We couldn't afford DCL regularly if we did balconies every time.
Set up your own shore excursions - usually half the price. Use this cruise forum for infomation or use cruisecritic.com for port and self-excursion research. Limit yourself to either 1 or 0 excursions. There is so much to do yourself at ports and on the ship, that we have not found excursions always necessary. This saves a bunch. Find a good packing list (do a search on this cruise forum for ' excel packing list ' and you'll find a good one). This helps you bring everything you need so you are not having to buy things on the ship, in port, etc. Finally, set a goal to spend only $x on the ship. We've taken cruises and spent less than $25 per person on the ship. We never let our youngsters have spending privileges - we gave them a small notebook with $25.00 written in it. They had to ask every time they wanted something, we'd discuss and if they bought it, they did the math. (Of course, we had to set this expectation and process well before we boarded the ship, so they knew what to expect.) Once they were 16 and 17, we let them have spending privileges, but still allowed them only $x and anything beyond that they had to pay themselves. We quit buying souveniers years ago - really wasn't any value for us.
Do the math and figure out if it is cheaper to use DCL transportation or to rent a car to the port. Usually for us car rental is cheaper, but car rental has increased significantly over the last year.
I hope this helps some. Keep reading the boards and don't be afraid to ask questions - everyone is so helpful here - only because of these boards have we been able to do WDW and DCL as many times as we have (of course, I'd like it to be more, but ...
