DH is a service writer for an auto dealership and I'm a graphic designer with my own small business. We've worked our way up to 3 weeks at WDW for our annual vacation the past 2 years. It takes a LOT of scrimping, saving and planning to pull it off.
Time off is tricky - DH only gets 2 weeks paid vacation, so he saves up his sick time time to take the extra week. I'm much more flexible with my own business, but even though I do a lot of planning to clear my desk before we go, I still usually end up bringing my laptop to take care of the little things that crop up while we're gone.
In terms of cost - it helps tremendously that we pull our travel trailer to Fort Wilderness and stay there with our dogs. Ends up costing us about as much as a value resort - a bit less if we luck into an AP or
AAA discount. The ability to cook some meals saves on food (we usually eat 1 meal out each day), and bringing the dogs with us saves us the expense of having to kennel them (plus we just love traveling with them!) Plus we just LOVE the Fort and all it has to offer.
When it comes to meals, we've done a lot of research about what's available and have found ways to save while still enjoying eating out - a big part of any vacation IMO.
For park tix we've found that by purchasing APs and planning so that we get 2 year's worth of trips out of each (6 weeks total) we save a TON there alone. We also take advantage of the discount perks that go along with the APs - namely the TiW card, which we can also use over 2 trips and has easily saved us several hundred dollars.
At this point our friends and family are playing into our Disney habit - giving us Disney gift cards for birthdays/Christmas - and we also save up points on our Disney Visa throughout the year (they paid for our
MNSSHP tix last year).
We've been to WDW often enough at this point that we don't buy many souvenirs anymore, so we save a good bit of $ there too.
In the end we've come up with a way to spend 3 weeks at WDW (on property) for what the average week-long package costs. It's not easy, but we think it's worth it for the fun and relaxation we have while we're there.
