While it is never guaranteed, for the past few years Disney have offered 'free' Dining plans when you book a holiday with them in advance. These typically become available to book at end of April/beginning of May, for holidays the following year. - usually for holidays between January and September, but excluding the Easter holidays.
Typically if you book a Value resort, you get a 'free breakfast' plan, Moderate resorts get a quick service plan included, and Deluxe resorts get a regular dining plan included. You can read more about these dining plans here.
But you can also choose to pay the difference to upgrade the free Disney Dining Plans - so upgrade the breakfast to a quick service, or the quick service to a regular plan, for example - all upgrades are possible. So, should you?
The Dining Plans are great for dining when in Disney - they offer between 20-40% discounts compared to purchasing the same food out of pocket - but this relies on you choosing the most expensive menu items and using every dining credit available to you. But of course you are not actually paying full price as this is an upgrade, so a proportion of the plan is free to you. So it is a little harder to decide if the upgrade will be better for you than paying for the extra meals at the time.
In making the decision about whether to upgrade your free Disney Dining Plan, we recommend you consider two things. Firstly, make sure you understand exactly what you are getting free and how much you'll utilise them - and therefore if you will need the additional meals in the upgrade. And secondly, compare the cost of the upgrade to the cost of the extra meals.
Note, we have never recommended the Deluxe Dining plan. I'm sure there are some circumstances where you might make the most of it, but for it to be cheaper than paying as you go, you need to be eating at table service restaurants so often that you will have very little time left to actually enjoy the attractions and entertainment at the parks. So for this article, we have focussed on upgrading to the Quick service, or regular Dining Plan.
Upgrade your free Disney Dining Plan: Understanding your freebie
The 'free breakfast' plan is pitched as that, but as it is not a plan you can otherwise buy, it currently translates to one quick service credit for each night of your stay. Those credits work like any other quick service credit - they can be used at any time of the day, at any time over your holiday period, and at any quick service location.
The quick service plan gives you two counter service meals and two snacks a day, plus a refillable mug that can be used at your hotel for hot drinks and soda. Upgrading to the regular dining plan changes one of those meals into a sit down, table service meal.
So consider how much you plan to be in Disney and therefore how many meals you may actually need. For example, if you're planning on exploring outside of Disney on half of your days, (Universal, Sea World, shopping etc), you may not choose to use credits in Disney at all on those days. If so, on the breakfast plan you'll have enough credits for two meals on each of your Disney days. On the quick service plan, you'd have plenty of meals - so consider how many table service meals you'd want on those Disney days. In either case, upgrading plans may not be worth it as you'll only utilise it for part of your trip - it could be cheaper to buy any additional meals as you go.
Conversely, if you'll be in Disney for the majority of your stay, on the breakfast plan you'll definitely need to buy more meals than you've got credits, so at the very least consider the quick service plan. And if you plan to eat a lot of table service meals, the regular plan may be better for you. In these scenarios, an upgrade could be an easy way of knowing your costs in advance and perhaps saving a little money.
Upgrade your free Disney Dining Plan: Cost of the upgrade
So you've decided that you want an upgrade your free Disney Dining plan, in theory - but is the cost of your upgrade cheaper than what you might otherwise pay at the time?
In 2020, upgrading from the free breakfast to the quick service plan will cost £27 per adult per night and £12 per child per night. For this you get an extra counter service meal and two snacks a day for every night of your trip, plus a refillable mug that can be used at your hotel for hot drinks and soda. Would you otherwise spend that amount per person, on an additional counter service meals and snacks? We think this depends entirely on the individual.
To upgrade from quick service to the regular plan in 2020 will cost roughly £17 per adult, per night, but only £3 per child per night. Would you plan to spend that on table service meals over the course of your trip? Remember you need to additionally budget for tips at table service meals - 15-20% of the cost of your meal. This upgrade from quick service to regular dining plans is reasonable - if you do prefer to have table service meals, you will easily spend this.
This means to upgrade from the free breakfast to the regular plan in 2020 will cost £44 per adult, per night, and £15 per child per night - this will give you an additional table service meal, 2 snacks and the refillable mug, on top of your counter service meal previously designated for 'breakfast'. As long as you make sure you use your credits - i.e. eat all these meals at Disney, you could easily spend this.
Upgrade your free Disney Dining Plan: Does Magic & Wishes upgrade?
Without fail, we upgrade (where necessary) to the regular Disney Dining Plan. We rarely venture out of Disney, so we eat all our meals there. And we love trying out a variety of snacks. It makes sense financially for us to upgrade to quick service from the free breakfast, and we also don't want to eat only counter service meals each day - so for us the regular dining plan is the best choice. Food is a big part of our Disney holidays - there are fantastic restaurants in Disney World and we want to make the most of them, without worrying about the cost. We'd never have purchased the Wagyu Beef from Tiffins in Animal Kingdom, without the Dining Plan, for instance. This wont be the case for everyone, but if you do decide to upgrade to the regular plan, make sure you book your restaurants in advance. You need to make the most of those credits you're purchasing. We are sure you won't be disappointed.

Wagyu Steak on the Dining Plan at Tiffins