With 5 years to plan there are a lot of things that you can do to save, and you might be surprised you might reach your goal in 3 years
So thinking out loud here we go.
Set up an Disney Vacation account and everything you earn and are earmarking for Disney must go in it. A simple saving account would work - watch the fees, and the balance amount.
Start off your Disney savings with a Garage sale, like a really well prepared for garage sale, go through everything every closet's, drawer's and totes you have. Everyone should help as everyone benefits. Depending on time of year you should easily make a couple hundred dollars, We had one when moved at we made 350.00. Also set up for a charity to come and pick up the anything left, the last few time I did "Vines of hope" its a home for young people who need a place to go after rehab, to help them start over. Make sure to get a donation form for the cash amount you can use this for your taxes. Then have a garage sale once a year.
Check your area for a Kids to Kids clothing style shop, where you bring in kids clothing, baby items, some toys, or books. They pay cash for your items or will give you store credit which is normally more than the cash they will give you. Make sure to read what they are taking ( seasonal) and the guidelines.
Start a change jar, and have everyone throw in their change. You will be surprised at how much change you can save this way. Have everyone help roll the change, if you take it a change machine they take a percent.. Plus this is fun for the family to do.
Create some type goal poster board, and have everyone help. This keeps everyone focused on the goal.
Packing your lunch, including drinks and snacks will save you a ton of money. I took my lunch to work 4 days a week, along with snacks and drinks, it was a dollar for a coke/soda out of the drink machine. It saved me around 50 to 60 dollars a week x 4 weeks that's around 200.00+ dollars a month. Get a nice lunch bag or mini cooler, and different containers to easily make lunch, even some Disney napkins, for add incentive to save for your trip. For me I made lunch the night before, packed in my insulated lunch bag, so all I had to do is grab and go. Keep something like a can of soup, or tuna pouches in your desk.
Meal planning, Seasonal cooking, freezer meals and Couponing all of these go hand in hand. While this does taking some time its really worth it. Make a list and stick to it... Which for me was the hardest thing to do. Now in saying that if you come across a really good deal get it, for instance if you have planned to make meatloaf for dinner, and you need hamburger meat on the list and the family packs are on sale, you should go ahead and get it, but know what you are going to do with. So many things you could do with it, make red sauce, taco meat for tacos, nachos or burritos, meatball for subs and you can freeze for later on.
*Check out places like Aldi for pantry staples, I started going for a few things and now I go once a month, they have a great selection of dried fruits, nuts, granola. I also pick up cans of chicken, beef and veggie broth, cream of mushroom soup, cans of mandarin oranges. They also have lots of spices, sugars, oil's, and items for baking, at amazing prices.
*When using your coupons, take the time to match them with your local grocery ad, or if the grocery store has store coupons were you can stack them for add saving.
Then pay yourself the saving... Okay I saved 10.00 on groceries with my coupons, then transfer 10.00 into the vacation account.
* Don't forget looking for coupons at sites like "retail me not" when out shopping.
* Sign up at your favorite stores for shopper rewards. I have 50.00 in rewards at Penny's that I am going to spend more than likely toward some Christmas gifts.