The idea for our October trip was born sometime during the sultry, humid days of last summer. I think we were feeling a bit stir crazy, a bit too chained to our desks and confined to the house in the air conditioning at night. We were a few months off our incredibly successful April family trip, and I can’t remember which one of us had the itch first, but oh, did we have the itch.  It also didn’t hurt that I possessed both a) a highly sought-after Disney PIN code (What’s a PIN code, you ask? Read this.) for free dining, and b) knowledge of an upcoming 40% off (!) room-only discount at deluxe Disney hotels. So, a game of Disney discount roulette began. When to go? Where to stay? Which discount to use? Which discount would save us more money?

Originally we began planning to book a December trip. In fact, we *did* book a December trip (everything except the airfare, that is. Good decision!).  And then I started to feel….weird about it. December was shaping up to be a busy time at work. I don’t exactly love to fly, and wasn’t thrilled about the idea of airport delays or cancellations or de-icing procedures.  Granted I had always (and still do!) wanted to see Disney at the holidays, but for some reason it just didn’t feel right.  I tweaked. I tinkered. I moved our days slightly, and then panicked when I realized I had lost all of our dining reservations and it was impossible to get new ones in our new week.

So, well, we kind of said to heck with it. Let’s not going in six months, let’s go in three months!  It turned about to be a good plan – the discounts worked out better, we could attend the Food and Wine Festival, and neither of us would face much difficulty getting out of work for seven days. Because yes, my friends, this was to be a trip of epic proportions, ten days of eating and drinking and riding rides and taking photos and not checking work e-mail. Go big or go home, that was our motto.

Once again, we did the Disney discount math.  We eventually decided on the Animal Kingdom Lodge. We splurged a tiny bit for a pool view. Both of us were excited to book this reservation; after all, we had loved AKL in April, and this time we would have a chance to stay in the main (Jambo) building and be closer to the food and the action. We decided against the dining plan (too much food, too expensive, vegetarians can’t really get their money’s worth, etc), but booked a lot of good meals.

What can we learn from this? Well, spreadsheets are your best friend. Before deciding whether or not to buy the dining plan (regular or deluxe version), I actually figured out by hand the cost of each meal we intended to eat, so as to compare the out-of-pocket cost to the cost of each dining plan:

Ultimately, we decided that neither the regular nor deluxe dining plans offered us the savings or flexibility we were looking for. I can’t tell you how many hours I tinkered with the above spreadsheet, but it was in the long run completely worth it.

Your game of Disney discount roulette will depend greatly upon what discounts are available and at which resort(s) you intend to stay.  It’s worth calling a few Disney reservations employees and having them run different scenarios for you. For us, a 40% room discount outweighed the value of free dining, but for others – especially with larger families – free dining could be worth its weight in gold.

Lastly, I think it’s worth mentioning here (although I’ll subsequently discuss it in more detail, I’m sure) that we did not rent a car. This came back to haunt us. At the time, though, CP in particular was enamored with the idea of being sort of benevolently trapped on Disney property, forced to enjoy the magic 24/7. Well, let’s just say that fantasy was short-lived. We are now committed car-renters, and this nerd advocates that you should be, too.

Up next: Day one of our ten-day odyssey.