I need some help! I'm sure my very knowledgeable and wonderful readers can assist me...
I've been looking at the Tables in Wonderland card, and it definitely seems to make sense. Most of the places we plan to eat at are part of the program, and 20% is a good savings, especially with 4 adults worth of food and alcohol!
Do any of you have experience with it? Do you recommend it? And what may be a stupid question: is it good for a year?
I'll be getting an AP this spring, so this is the first time I've been eligible for one. Though I did hear that they are going to be making them available to DVC members as well (not sure what the price will be in that case). It just seems too good to be true, so I was hoping to hear from folks that have used it!
Your May plans are really shaping up!
I'm also interested to see what people say about the TIW card because I'm going to get one too. Since I'm doing 2 trips next year, I will also be buying my first ever AP in April.

So while I can't offer any advice up yet, I can in April once I come back...which would actually be before you go in May

Day 2 sounds like fun!
We had the Tables in Wonderland card and loved it! It cost us $75 (if I remember correctly) and I think they're actually good for 13 months. Not sure why.It pretty much paid for itself after a couple of meals since dining at Disney is so expensive. I'd say that if you've got two trips planned within the year and you're going to be buying drinks, you can't go wrong with the card. It also adds 18% gratuity automatically, which I liked because it meant I didn't have to figure out the tip!
There was only one restaurant that we went to that didn't accept it, and that was Yak&Yeti. I know there are others, but it seems like most of the restaurants do take it now. Oh, and you can use it for yourself and up to 10 guests (or maybe it's 10 people total) so that would be great for your trip in October with your friends.
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I'm bummed to hear that Yak and Yeti doesn't take the TIW card. We were planning on eating here again, but I'm wondering if I should take full advantage of the TIW card and eat somewhere else in AK that takes it. But this was one of our favorite meals last trip, so it's hard to pass up!