Should I do free dining or buy annual pass? Help me decide

[AvaLovesMickey]

I am not sure if this is the right forum, if not if you could direct me to the right one. I've tried crunching numbers but I need another set of eyes to help me.

There are 5 of us (me, husband, 3 kids but my youngest turns 3 in December).

In September this year we plan to go for a week (buy 5 day passes, no park hopper). Assuming there is free dining, we plan to take advantage of that and pay rack rate for a moderate resort. After adding up sit down meals for a week, 1 sit down meal a day for 7 nights, it would be well over $1,000 saved if we use free dining.

I would like to go back again before September 2016. Possibly Thanksgiving this year, like we did last year (yeah, I know, we should have purchased an annual pass during Thanksgiving last year). I live in Georgia so we could always drive to Orlando in a day.

Anyways, after crunching numbers, and seeing how expensive the food is I am wondering if I should not buy an annual pass in September and just take advantage of free dining. We love character meals.

So I've read it takes about 11 days to break even for the annual pass, which does not take into account the benefits Tables of Wonderland card. Knowing that information, it seems like it would still be more expensive than doing the free meals for a week. But I am a little "Disney overwhelmed" crunching these numbers now. So anyone willing to help me decide?

My theory is would it be better to take advantage of free dining and then buy the annual pass next time we return? Keep in mind, we prefer at least a moderate resort (queen beds a must for us); my youngest doesn't turn 3 until December, and there are 5 of us total.

Thanks for your help!!!

 

[Disneylover99]

Do a free dining package. Keep your five day tickets so you can book fp's and upgrade to an AP after you get there.

 

[AvaLovesMickey]

Ohhhhh you are so smart.....why didn't I think of that. PERFECT. So I get the free dining and then I can upgrade without losing money that I put towards the tickets, right? Thank you.

 

[bsbrady]

Remember as an AP holder you can buy the tables in wonderland card, which gives you 20% off of all table service meals, you will also get AP discounts including resort discounts, if you stay in a deluxe the discount is 35%

 

[JanaDee]

Remember as an AP holder you can buy the tables in wonderland card, which gives you 20% off of all table service meals, you will also get AP discounts including resort discounts, if you stay in a deluxe the discount is 35%

Do your homework on the TIW card. It was never worth it for us. When I was looking into it, you had to spend at least $500 on food just to break even on the cost (amount may be different now).

 

[bsbrady]

Good point, but remember the card is good for a year, and they will be making multiple trips. She mentioned that they will have a sit down dinner for 7 nights. The card might pay for itself on one trip, but most definitely over multiple trips.