Tips for Booking Your First Disney Trip

Tips for Booking Your First Disney Trip

Booking your first Walt Disney World trip can be daunting but don’t worry I am here to help. Getting it right can not only save you money but maximise the magic while there. While it is possible to book a whole package including flights, accommodation, park tickets, car hire etc through sites such as Travel City Direct or Virgin it will cost more so it is worth considering doing it yourself. Hopefully, this post based on our top tips and experience of booking will help make the process easier.

Choose a Date to Visit

If you are flexible when you can visit it is worth checking out the crowd calendars for the best times to go. There are a few different calendars but my favourite is the WDW Prep School one below.

Walt Disney World Crowd Calendar 2018-2019

The calendars use a combination of season (primarily weather), day of the week, whether US kids are in school, park events (e.g. Food and Wine Festival, or new rides opening), local events (e.g. spring break), holidays, and overall park popularity at the time.

As we are constrained by school holidays, we usually pick the last 2 weeks of August/start September when the US schools go back and the crowds tend to be a little lighter. It is very warm during this period and as it is hurricane season you can expect some epic thunderstorms but none so bad it spoils park fun. Halloween decorations start appearing in Magic Kingdom at the end of August and last year we were lucky enough to attend Mickey’s Not So Scary Halloween Party which is an added bonus of going this time of year.


Next decision is whether to stay in a Disney Resort or off-site. Your budget and the amount of space required are big factors here, as does whether you plan to spend all your time at Disney or intend to do Universal, SeaWorld, Busch Gardens and so on during your trip.

Staying On-Site

We like to stay on-resort and get fully immersed in the Disney experience. We book directly through Disney as soon as the Free Dining offer becomes available which tends to be in October or November. The 2019 offer also includes 14 for 7 days tickets, $200 Disney Gift Card, 15% off at, Memory Maker and Extra Magic Hours. It is worth booking as far in advance as possible to ensure you get the accommodation you want, rooms become available to book 499 days out. The resort accommodation falls into three categories Deluxe, Moderate or Value and the dining plan varies depending on which you choose but you can upgrade your plan for an extra cost.

Disney Dining Plan

Our favourite resort is Port Orleans Riverside which is a moderate resort and has a lovely relaxed atmosphere with great swimming pools, waterslides, food court, restaurant, a bar where Yehaa Bob Jackson plays and the Riverboat to Disney Springs amongst other things.

Port Orleans Riverside

You also have access to to the facilities in Port Orleans French Quarter, we like to pop to the food court for beignets just like Tiana makes in The Princess and the Frog and spend some time in the pool while there.

Port Orleans French Quarter Pool

The Deluxe resorts include the Contemporary which is strolling distance of Magic Kingdom, the Polynesian where ‘Ohana is found and Animal Kingdom Lodge to name a few. Out of the Value resorts Art of Animation and Pop Century are family favourites.

The ease of transportation is a definite benefit of staying on resort as you can get the Magical Express from the airport direct to your Disney Hotel and hop on a bus, boat, monorail or just walk to the parks while you are there.

Rent Disney Vacation Club Points

Disney Vacation Club (DVC) is Disney World’s version of timeshares where members pay to buy points which allow them to stay in Deluxe accommodations during the length of their contract. Sometimes they don’t use all their points and instead rent them out privately or through sites such as or DVC Rental Store. There are 14 DVC resorts to choose from and with villas available which are ideal for larger groups. You can still link up to My Disney Experience which allows you to book FP+, make advance dining reservations and so on. Housekeeping, however, is a Trash and Towel service instead of a daily maid visit which you get if you are staying on-site. For more info on DVC check out these FAQs.

DVC rooms become available for reserving 11 months out and book up quickly so you need to book early or be flexible in the dates, resort, and room type that you’ll accept. You could also opt for a split stay between multiple resorts to accommodate your dates, especially during particularly busy times. Unlike booking accommodation through Disney where you pay a deposit, you will need to pay in full on confirmation of reservation.

Off-Site Options

If you are staying off-site there are a number of hotels on International Drive (I-Drive) which are not just convenient for Disney but Universal and other attractions too. Make sure you check for extra hidden charges such as parking, WiFi and whether there are shuttle buses to the parks if you are not planning on hiring a car.  For larger groups, a villa or house may work out better and there are lots of great ones available with private pools so you can chill out when not at the parks.

Park Tickets

If you are not booking a package through Disney and availing of the 14 for 7 days tickets, check out Attraction Tickets or Floridatix where you can choose from different options. These sites often have flash sales and offers so sign up for alerts and compare before you buy.

Booking Flights

Again the more in advance that you can book, the better. We monitor the prices on Kayak and Skyscanner for the same period as our holiday the year prior to going to get an idea of when the prices are at their lowest and what we can expect to pay. Setting up an alert is easy on both Kayak and Skyscanner. We aim to keep flights to £2,500 for a family of 5.

WDW Booking - set up flight price alert WDW Booking - set up flight price alert

In general, it is best to book a year from the date you wish to travel to get the best prices. If you can find a direct flight for a reasonable price then opt for that. In the past, we have flown via Atlanta with Virgin and Delta which works out well as you clear customs at Atlanta leaving one less thing to do upon arrival in Orlando. We have also flown with Lufthansa via Frankfurt which, personally, I wouldn’t recommend, the flight was not a good experience and Frankfurt airport is quite painful when it comes to security and transferring between terminals which resulted in a very stressful end to our holiday.

Car Hire

For car hire I recommend Alamo which we have used many times in the past and have always been happy with the service. Word of warning, don’t feel pressured to buy collision damage waiver (CDW) insurance, it is better to buy it in advance. Check out this article for more info on how to avoid being ripped off.

What’s Next

I hope these tips have been helpful, please feel free to get in touch if you have any questions and I will do my best to answer. Next, check out my Disney Countdown Calendar for the all-important milestones and look out for my upcoming posts on booking FastPass+, Advance Dining Reservations and more.

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