Ever since my childhood, I have DREAMED of going to Walt Disney World, Florida.

I’m not even really sure how or why this Disney obsession of mine started.

I remember watching Cinderella on repeat as a little girl and adoring it but I was never the biggest fan of the other Princesses of the time (There was really only Snow White and Aurora in the early 80s, wasn’t there?!) and given that the Disney Princess phenomenon didn’t really hit the big time until the 90s with the introduction of Ariel, Jasmine, Belle and Mulan – I’m honestly just not sure where my love for Disney came from.

But still – I remember seeing the TV adverts and begging my parents to take us there on holiday. Of course it was fruitless – my parents couldn’t see the appeal of a visit to the US at all and my mum was terrified of flying – so I clung on to the dream into adulthood.

And that’s how its remained ever since – a distant dream! Every year I would find myself pricing up imaginary holidays on the Disney World website, imagining how wonderful it would be to go there with my own children – and every year I’d come to the realisation that we simply couldn’t afford it.

But a year ago – something magical happened! All of the stars aligned at just the right moment and by some miracle – we could finally make it happen. (Or, if you want to be less poetic about it…I secured a big contract in my work life which amounted to exactly the price I’d been quoted for the Disney trip of our dreams….no brainer!)

With the holiday and flights booked, we’re getting ourselves ready to head off to Florida in just 9 months time and I plan to share my experience of every inch of our dream trip – from the planning to the packing, and everything in between. We’ ve added two days on to the end of our trip so that we can stay off-site and do some of the things we want to like visit the outlet malls and Walmart, I can’t wait!

This will probably seem slightly odd if you’re not a Dis-nerd like me, but trust me – Disney Holiday Planning is a *thing*. It’s a BIG thing actually, with people (me included!) spending months on end researching and planning out every inch of their trip – and who can blame them?! When a holiday is this pricey, you want to make sure you’re squeezing every last drop of enjoyment out of it – or at least, I do!

So to start off, I’m going to tell you all about how we decided when & where to stay during our trip, and how we found the best deal!

The Pre-Planning!

Now before I get into this – let me just explain that although I keep referring to “we” in this post (force of habit!)…make no mistake about it, this has all been 100% a solo effort!

If you were to ask my other half what price we’ve paid for this trip, how the Disney dining plan works, what plan we’re on etc then I can absolutely guarantee you that he would be utterly clueless! I’d even hazard a guess that he wouldn’t even know which resort we’re staying in.

Not for lack of me telling him and boring him senseless about it all, but simply because he just doesn’t get it – he seems to think that magical holidays just “happen” without any of all the fussing and planning that I do for months – hmmm, we agree to disagree on that one!

I take this Disney holiday stuff SERIOUSLY. I’ve bought planning guides, I have a whole dedicated a4 Notebook full of tips and plans for our trip – I’m leaving nothing to chance!

It might sound like it’s all a bit much for a holiday and you might even think that this sort of planning sucks the fun out of it but noooo – you see, I’m a Virgo!! Planning is my porn. I enjoy this part of a Disney trip almost as much as the holiday itself! I LOVE IT.

So naturally…as a (somewhat obsessive) planner, I spent a fair bit of time pricing up imaginary holidays on the Disney website for a long time before we actually booked.

I made sure I knew when the best sales usually happened, I made sure I knew which companies seemed to offer the best deals, and I researched low crowd prediction calendars.

As I’ve waited so long for this trip, I wanted to make sure that our first time we everything I dreamed of.

I didn’t want to settle for a different time of year – I had my heart set on going during Hallowe’en season and I didn’t want to compromise.

I didn’t want to stay off-site for our first trip – I wanted our first experience to be an on-Disney property stay.

I didn’t want to go for any less than 14 nights.

And so, from pricing up holidays for a family of 5 at that time of year, I knew that I was generally looking at between £7,500-£10,000 depending on which hotel we chose.

Which to me – is VERY expensive.

However, from doing my research I realised that by far our best chance of getting an affordable price seemed to be during the Free Disney Dine offer that Disney runs each year for a limited period.

And so, I made a note of when that was likely to come up, and I waited.

Finding Our Deal

The Free Disney Dine Offer started in April , and so I spent a day or two pricing up our trip with a number of different companies.

I looked at various travel agents, and I looked directly with Disney themselves.

And I found the cheapest deal with a company called Attraction Tickets.

Now I have to admit, I was (and still am) nervous about booking with a third party company – I like to book directly with a company wherever possible as I think it’s usually less of a headache and there’s far less chance of a huge company like Disney disappearing overnight.
But Attraction Tickets are ATOL and ABTA protected, and are a reputable company – I did plenty of research and decided I felt safe enough to go ahead and book.  You can also save money on discounted disney vacation package with resort hotels in Orlando Florida too. 

We booked way too far ahead to be able to get flights included, so we were going for a hotel & park ticket package with Free Disney Dining included.

We were offered a choice of two moderate resort hotels – Port Orleans French Quarter or Caribbean Beach Resort – I spent some time researching both hotels and although POFQ looked like it might be slightly better from an adult perspective, I knew the kids would go crazy for the Pirate theming at Caribbean Beach and the pool looked amazing – so I went for that one.

We decided to upgrade our Free Disney Dining plan from the quick service plan, to the Standard plan which means that we get 1 quick service meal credit, 1 table service meal credit and 2 snack credits per person per night of the trip.

This cost us an extra few hundred pounds, but considering the fact that we all LOVE meeting the characters – it was worth it to us, as it means we can book lots of character dining experiences without paying out of pocket (We plan to book 10 character dining experiences if we can get the reservations….so it will more than pay off!)

And so, our grand total for 14 nights in a moderate hotel with upgraded dining plan for five people came to £5,200.

Still a lot of money – but far less than I’d ever been quoted before on any of my mock bookings! I was very happy with that price.

The great thing was I was also able to secure the price with just a £200 deposit – I don’t need to pay the balance until 8 weeks before we travel, so I don’t need to worry about giving all of our holiday money to the company too early.

Finding The Best Price For Flights

With our holiday package secured, it was a waiting game until our flights were released and I have to admit – I was nervous about this!

Sure we’d got a good deal on our holiday price, but the fact was – we could still end up paying thousands for our flights, pushing the cost of the trip way up.

Flights are generally released about 12 months ahead of time, although this varies depending on the airline.

So from September 2018 (2 years before our departure date!) I kept a close eye on flight prices – trying to spot patterns in the pricing, trying to figure out when the cheapest prices went up.

It seemed to me that the best prices were usually offered in the Boxing Day sales – and regular Florida travellers in various Facebook groups all seemed to agree.

So I kept our money to one side, and on Boxing Day – I hit the sale!

Unfortunately for me, luck was not on our side.

Virgin were quoting us £3,500 for direct return flights in their mid-economy seats. This was around £1000 more than the same flights had been advertised for just days previously. I kicked myself for not booking them then!

I tried BA instead and couldn’t believe my eyes when I was quoted over £5,000 for the same flights!

I was worried now…if I ended up paying this much for flights, then our trip wouldn’t have been a good price at all.

I was torn on what to do – worried that the prices would continue to rise, but I decided to hold my nerve and wait a little longer.

So after New Year, on January 5th, I took a look at the prices again.

BA were charging a similar price.

So I tried Virgin….they were coming up at £2,500. A better price, but still a bit more than I’d hoped to pay.

I was about to go ahead and book, but something told me to try checking for different dates – so I did. I set the search function to show me prices for flight dates close to my desired ones.

Up came an outbound flight a day before my desired date, and a return flight 2 days after my chosen one.

The total mid-economy price for all 5 of us was £1,700!

The best price I had EVER seen throughout all of my searches.

I thought about it for a moment – knowing this would mean I’d need to find off-site accomodation for 3 extra nights. But I decided to go for it – deciding that although I may still end up spending the additional £800 on hotels anyway, I’d rather pay that money for extra nights in Florida than spend it on the plane!

So we booked and secured our £1,700 flights – taking our holiday total to £6,900 – again, expensive but by far the best price I’d seen for 14 nights on site for 5 people at our chosen time of year, with dining included.

As a bonus – we went on to Booking.com to look for accomodation for our extra nights, and managed to sort it out for under £400 – meaning we still saved more money than if we’d gone for those plane tickets on our original date, AND we get the 3 bonus nights too!

So that’s how we got our deal – I’ll leave you with my top tips and resources for booking your trip and finding the best price. And I’ll be back soon with a post all about planning and booking our Disney Dining Experiences for the trip!



My Top Tips For Booking A WDW Holiday

1) Decide Your Ideal Dates

Maybe you’re restricted to school holidays or by work, or maybe you just know there’s a certain season that you want to be there for…this obviously makes narrowing down your date options much easier.

Personally, it HAD to be Halloween season for me – I want to do Mickey’s Not So Scary Halloween Party and it’s only on in certain months of the year, so I knew we needed to be there during September or October.

If you don’t have a specific season you’d like to see and you can travel at any time, then be sure to consult the Crowd Calendars.

They’re not always accurate but they are a good indication of when to expect the parks to be a little less busy and this is also usually reflected in the prices, with better deals available during these “off peak” times.


2) Try To Plan 2 Years Ahead And Do Your Pricing Research

If you can plan 2 years ahead of time, then you’ll be able to do some “practice runs” with your bookings for your holiday package and your flights too.

So for example if you plan to travel in 2022, then you can spend 2020 doing some mock bookings for 2021 – to get an idea of when and where the best prices are usually available.

Make a note of your findings to refer back to when its time to book for real! I found this to be such a big help and it definitely helped me to find the best prices.

3) Compare Prices Between Companies

No matter what you do – never look at just one company for prices! You want to shop around as much as possible.
We looked at TUI, Virgin Holidays, Hays Travel, various Florida specialist independent travel agents, and with Disney themselves.

When we go to Disneyland Paris, I usually find that booking direct gets me the best price – but that was NOT the case with Disney World. Attraction Tickets offered a cheaper price than Disney were offering directly, and with better perks too (We got a $100 Disney Giftcard as part of our booking).

4) Consider Whether You Want To Wait For The Free Dine Offer

From doing my research, I knew that booking our trip during the Free Dine offer was going to be the best option for us – and it also meant that I wouldn’t need to worry about saving up a ton of spending money for food or allocating a dining budget during our trip.

I know that our meals are pre-paid for, and we can eat without worrying about what we can afford to spend – which will make for a very relaxing trip for me!

However, some people find that Disney increase their overall price during the Free Dine offer so that its not actually truly “free” at all – a lot of people also prefer not to include the Disney Dining plan as they can eat cheaper without it.

It’s all a matter of personal preference, so look into it and decide whats best for you.

A helpful website for doing this is https://touringplans.com/walt-disney-world/dining/menus which has links to all of the Menus for the restaurants on site, along with pricing.

5) Hold Your Nerve With Flight Prices & Look At Alternate Dates

Trying to find the best flight price is scary business!

Use websites like Skyscanner to help you find the best deals, and be aware that the best prices seem to be either when flights are first released, during the Christmas sales or during the January sales.

If you don’t see a price that you like right away, do try to hold your nerve and check back…you may get lucky!

But don’t hang around too long – if you see a price that you’re ok with, snap it up!

Remember that airline websites use cookies and it’s generally agreed that once you’ve searched a flight once, the price will increase next time you look so DELETE THOSE COOKIES from your browser before you search again to make sure you’re getting the lowest price possible.

Remember to check with different airlines, and know that you can always choose to fly indirect or without baggage if you’d rather – these options both save some money.

6) Know There Are Cheaper Alternatives

As I said at the start – I had certain “non-negotiables” when booking this trip.

It HAD to be Halloween, it HAD to be 2 weeks, it HAD to be direct flights with a good baggage allowance, and it HAD to be on site.

However, if I’d been flexible on any of those things – I could have saved money. Quite a lot of money actually!

You can book holidays to Orlando with flights included, staying in a villa with Disney park tickets included for less than £4000 for a family our size. Pretty much half the price we paid!

So if you’re not dead set on things, shop around and see what you can get – I will certainly be looking to stay off property for our next trip!!


Do you have any tips to share? I’d love to hear them!!


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