Walt Disney World Vacation Planning Guide

Canadian Guide to Walt Disney World Vacation Planning

A Canadian’s Guide to Planning Your Walt Disney World Vacation

The prospect of embarking on a Walt Disney World vacation is an exciting time for any Canadian family.

All too often, however, the initial excitement can wane as you get deeper into the planning process. If you’re new to Disney vacation planning, it doesn’t take long to discover that information overload can lead to feeling overwhelmed. Decision paralysis is unfortunately a common occurrence for new Disney travelers. The more you reach out for online advice and information from friends, the more confusing it becomes with differing answers and conflicting advice.

Disney Vacation Planning Has Become a Cottage Industry

Maurice's Cottage, Magic Kingdom, Walt Disney WorldThere’s a reason why an entire cottage industry has evolved around the planning of Walt Disney World vacations: it’s a very big place with an (almost) infinite number of vacation options and variables for any traveler to consider. In short, the biggest asset of Walt Disney World (being its size and breadth of vacation options) can also become its biggest liability—at least as it relates to Disney vacation planning for first-time travelers to Walt Disney World.

To help bring a sense of order to the Walt Disney World vacation planning process, I will outline the key areas that you will need to consider when planning your Walt Disney World vacation. I will cover the key decision points and a suggested order in which to make them. Nothing is written in stone, but I have learned from experience that if you are looking to bring a sense of structure to your Walt Disney World vacation planning, these key steps, questions and decision points will help to guide you along the way.

Regardless of whether you plan to book your Walt Disney World vacation directly, or use the complimentary services of a Canadian Travel Agent (such as me) who specializes in Disney Deluxe vacations, considering these questions in advance will help to make the Disney travel planning process go much more smoothly and lessen the likelihood of last minute oversights or unexpected surprises.

A few important points to remember before we begin planning your Deluxe Disney vacation

Go Easy On Yourself
You can drive yourself crazy with the minutiae of just about every decision you’ll need to make along the way. So go easy on yourself. Try to keep it fun. Just remember that there are only five of what I consider to be Walt Disney World Vacation Planning Golden Rules. Much of the rest of your planning is more about knowing the pros and cons of each question/decision that you’ll need to make so that you go into things armed with knowledge and with eyes wide open.

Minnie Mouse, Magic Kingdom, Christmas ParadeFor example, probably the number one most common question I get asked is “When is the best time to visit Walt Disney World?” Despite what anyone may tell you, there is no definitive answer to this question. “Best” is a relative term and everyone has their own set of variables behind the question. You may be told that the Christmas break is the absolute worst time of year to go. That may be true from the perspective of crowd levels in the parks—particularly the Magic Kingdom (which can be more likely to reach capacity early in the day during the week between Christmas and New Year’s). However, if this is when you have the time available for a vacation, then that is the time you will visit. You just need to be aware of factors like crowd levels so that you can plan accordingly and won’t be surprised by the volume of guests when you arrive onsite.

On the other hand, the Christmas Break is also one of the most magical times of the entire year to be at Walt Disney World, so there are usually several things to consider and absolute answers are not as obvious as you might think. It’s all about being armed with the knowledge and experience that you gain from your Disney Specialist Travel Advisor and other sources that you trust.

When Do I Think is the Best Time to Go?
For the record (and with all things being equal), I would say that the last two weeks of September are probably one of the most ideal times of year to visit Walt Disney World if you have no restrictions on your schedule. Crowds are down because most kids are back in school. The weather is still quite nice at this time of year. The Epcot Food & Wine Festival is usually under way and if you time it just right you might even catch Mickey’s Not So Scary Halloween Party in the Magic Kingdom.

My Disney Experience: Your First “Must Do” Task

My Disney Experience is Disney’s website and app that becomes the central hub of your entire Walt Disney World vacation. Over the past few years this technology has really grown and matured to the point that it is a very convenient and useful central source for all of your Walt Disney World vacation planning. There isn’t much that you cannot do in there. So be sure to go online to set up an account and download the corresponding app to your phone.

Disney's Boardwalk Inn, Walt Disney World

Seven Steps to Planning Your Walt Disney World Vacation

Questions You’ll Need to Consider Upfront

In creating this guide, my focus is on helping you understand the options and ramifications around each critical planning question so that you can make decisions with as few unexpected surprises as possible. We’ll keep this at a high level, as the planning will quickly become more customized when begin to drill down. The highest levels will be fairly common to all Walt Disney World travelers.

Step 1. When will you visit? Pick your travel dates.

When you plan to visit Walt Disney World can have an impact on your Disney travel plans. If your timing isn’t set in stone, there are several things to consider, including crowd levels, weather at different times of the year, special events that may be happening and so on.

Step 2. Where will you stay? Select your Walt Disney World Resort Hotel.

Check availability and pricing for your top choices of where to stay onsite, including room options, view etc. and then prepare to book your accommodations.

Step 3. Which Walt Disney World tickets will you buy? Choose your Disney World tickets.

Walt Disney World Magic Your Way tickets come with many possible options. Generally speaking, the more days you buy, the less expensive is the cost per day. Also, you will need to consider if you think you’ll visit more than one Disney Park per day (meaning you will need to purchase the Park Hopper add on) and also if you may want to visit a Disney Water Park during your stay (there are additional add-ons for things like this as well). In most cases, you will also book your tickets at the time you book your resort accommodations.

Step 4. Do you want to purchase a Disney Dining Plan? Decide whether or not to purchase a Disney Dining Plan.

Disney offers dining plans in three different sizes. They allow you to effectively prepay for your meals. Without going into too much detail here, it is impossible to quantify precisely whether or not there is a financial benefit gained from purchasing a Disney Dining Plan because there are too many variables. I suggest that you think of it this way: the dining plan can be more convenient to use (you won’t need cash on hand for all your meals, except for gratuities and any alcoholic drinks), however, you may find yourself consuming more in order to use up your credits. It’s a personal decision that is different for each family. For the record, in my family we do not purchase dining plans as we prefer to pay as we go and eat as we please.

Step 5. Where will you dine? Make your Disney dining reservations.

Walt Disney World has a lot of dining options between the parks, resorts and other areas such as Disney Springs. The most popular restaurants book up far in advance. Do your research and make a list of the places that you think you may want to visit for meals. You’ll want to make your dining reservations as soon as you book your accommodations (as early as possible) in order to get your top choices. However, be aware of where each restaurant is located. The trick is knowing how long it will take to get to each establishment from wherever you may be on a given day.

In short, book your dining while considering your itinerary loosely in the back of your mind. You’ll want to book dining first (because it is harder to get) and then build your itinerary around that (not the other way around). But you do need to consider where each place is located so that you can actually make it there without too much fuss.

Step 6. Which Disney park or parks will you visit each day? Start planning your Walt Disney World itinerary for the week.

In a typical week-long Walt Disney World vacation you will have six or seven days to visit the four main Disney Parks. Each morning you will likely head to one park, with the ability to double up on your favorites later in the week (four parks, but six/seven days). If you have the Park Hopper option, you may plan to visit a different park in the evening on a few days, after a mid-day break at your resort.

Another factor to consider is whether or not you will be attending any ticketed special events (such as Mickey’s Very Merry Christmas Party) or taking any special ticketed tours (such as the Star Wars Guided Tour). Tours and special events may be held only on certain days, which will directly impact your itinerary, park selection, dining and FastPasses. So there are many things to consider as you build your customized Walt Disney World itinerary.

Still another factor to consider is which parks have early Extra Magic Hours on which days during your vacation. Extra Magic Hours give guests of Disney’s onsite hotels an extra hour of access to a park in the morning (or hours in the evening) at different parks each day. Once you know when your trip will take place, go online and check the Walt Disney Work Parks Calendar to see which parks have early Extra Magic Hours. You’ll want to take advantage of those, particularly in the morning where it can be a real benefit (I find the later ones to be less beneficial as they are more crowded—which the exception of the occasional times that the hours go past midnight. Crowds will thin out after midnight and they can be fun times in the parks.)

Step 7. Which Walt Disney World attractions are most important to you? Make your FastPass+ selections. 

For each day of your stay (for which you purchased park tickets) you will be entitled to pre-book three attractions in one park. The first three for each day must be in the same park. After you use those three, then you can book additional FastPass+ attractions in a different park. There are some restrictions around which attractions you can book and these differ by park and attraction.

If you are new to Walt Disney World travel, then right about now is probably where you will begin to see the merits of working with an experienced Disney travel advisor who will help to guide you through the planning process. This is consistently one of the most valuable services that I provide for my clients (based on their feedback) and where they see the true value of decades of Disney travel that I bring to the mix. So please do not hesitate to reach out if I may be of assistance to you.

Be Our Guest, DIsney's Magic KingdomThe Walt Disney World Planning Conundrum:
Chicken or Egg? Parks + Fastpasses + Dining

Walt Disney World vacation planning is more art than science.

There are no hard and fast rules about what to book first (FastPasses, Dining or certain parks on certain days), because you may need to juggle parks on certain days to accommodate when you can actually get the FastPass that you want, or the dining reservation that you want. So it really pays to do your advance research and make a list of your must-do attractions and restaurants, along with any possible special events or tours.

All of this advance research will help you to adapt and make changes on the fly as your Walt Disney World vacation schedule begins to take shape.

Walt Disney World Deluxe Vacation Planning Services for Canadians

Are you a Canadian considering a Deluxe Disney vacation to Walt Disney World and looking for assistance planning your vacation? Please feel free to contact me for more information. It would be my pleasure to assist you.

Also, be sure to read my post on how to pick the right Travel Agent for your Disney vacation planning needs.

Mike Belobradic: The Finer Side of Disney Travel
Canadian Luxury Travel Advisor – Deluxe Disney Travel Specialist


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