As we enter 2020, people are starting to think about their 2021 Disney World holiday. 2021 is a special year because it's Magic Kingdom's 50th anniversary. Those celebrations might begin on or around October 1st (as Magic Kingdom opened October 1st, 1971), and if you paid attention to the free dining plan that was released in 2019 for 2020, you can see that Disney might have been warming up for this.
In recent years, the Disney free dining offer is introduced, but does get reduced in some ways each year. Luckily us Brits do get a pretty good deal compared the free dining offer Americans get which is quite a bit more restrictive. The free dining for 2020 (released 2019) was a little more restricted for us though, as some room types and resorts were completely excluded. What frustrated people the most about it though, is that the free dining didn't include October and beyond, which it did in previous years.
Sadly, don't expect that to change if Disney continue to offer this deal.
I said it then and I'll say it again now. That October change was likely Disney's way of breaking us in with the fact that it could be the same for 2021, due to the 50th anniversary celebration. We've seen quite a few people waiting and holding off their trips to be there for that.
While many people are cautiously optimistic free dining will continue, some people are coming to terms with the fact a year could arrive where it no longer gets offered. I don't think we're there yet though. I have no insider information so can only speculate, but cutting it off would likely lose too many families from the UK. I think it'll gradually get more and more restricted as the years go by. The parks appear to be quite crowded (if you haven't noticed). Of course, Disney being a luxury endeavour, if any economic downturn arrives (like a recession of pandemic), holidays are the first to get cut from people's budget, and its in those you can get some good deals. But don't hope or wish for either of those.
On the plus side to the 50th celebrations, I think it increases hope. That's because just like they did with offers in the summer before Star Wars: Galaxy's Edge opened, they're going to want to incentivise people to come before the big celebrations begin, too. Otherwise it's going to be quiet summer (infectious diseases notwithstanding).
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