Trip Planning 101: Deciding When to Visit Disney World

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The first step in planning a visit to Walt Disney World is deciding when to take your trip. This basic decision can have a big influence on the pace, mood, and cost of your vacation. Here’s a quick guide on how to choose the best timetable for your Walt Disney World experience.


Gather Your Tools

Before you sit down to plan, you’ll need to gather the following items:

  • A blank calendar. I like having one where I can see whole year in front of me, such as the 2014 calendar above.
  • Your school district calendar (if applicable).
  • Work schedules.
  • Calendars for your family’s activities: sports, church groups, dance recitals, etc.
  • Your personal appointment calendar.
  • The Crowd Calendar.
  • The Walt Disney World attraction closures schedule.
  • Access to information about Disney’s special events each month. There’s a great section about this in the Unofficial Guide to Walt Disney World.
  • Access to your favorite weather website, such as
  • Access to your favorite airline website, travel aggregator website (Expedia, Travelocity, etc.), or travel agregator app (Kayak, etc.).
  • Access to your favorite Disney discounts web site, like
  • Several colored pencils or markers.

Brainstorm Planning-Related Information

Before you sit down with the calendar, you’ll need to ask yourself some basic questions.

  • Are travel dates limited to school vacation dates? Or are you willing to take the kids out of school for a few days, or more?
  • Are there work-related dates that prevent travel? For example, you’re an accountant who can’t travel during tax season.
  • Are there family-related commitments that prevent travel? For example, your sister’s wedding is in August so you can’t go to Walt Disney World then.
  • Are there religious observances that prevent travel? For example, you need to be home during Easter.
  • Are there specific events at Walt Disney World that you’d like to experience? For example, Food & Wine Festival, Flower & Garden Festival, or Mickey’s Very Merry Christmas Party.
  • Does weather play a factor in your vacation enjoyment? For example, you don’t consider it a vacation unless it’s warm enough to swim. Or you’re uncomfortable carrying your toddler when it’s more than 80 degrees out.
  • Are there medical reasons not to travel at certain times of year? For example, your allergies flare during the spring. Or you become short of breath at temperatures above 85 degrees.
  • Do you have any absolutely 100% must-do attractions? For example, your son is obsessed with Star Wars. His (and thus your) vacation will be ruined if he doesn’t experience the Star Tours attraction.
  • Are there other people’s schedules to consider? For example, your dog walker is unavailable in the summer. Or your mother-in-law is traveling with you and must be consulted.
  • How important are low crowd levels to you?
  • How important is low cost to you?
  • Are there any habits of my traveling party to consider? For example, your teenagers refuse to wake up early on vacation, so you’d prefer travel when the parks are open late.
  • Are there special celebrations to consider? For example, your daughter has always wanted to be at Walt Disney World on her birthday.

To make it easy, we’ve created a handy Date Planning Worksheet, a downloadable PDF for helping you organize your dates.

Narrow it Down

If the reason that you’re visiting Walt Disney World is for a specific event, perhaps to run in the Walt Disney World Marathon, then selecting your travel dates is going to be easy. But most folks will have some more challenging choices to make. For example, while I personally make three or four annual research trips on my own, my family also likes to take one long trip to WDW each year (a full week), plus a long weekend bonus trip.

Let me walk you through my family’s planning situation for 2014 as an example to show you how you might tackle your task.

Here were my family’s considerations:

    My three daughters are now all in high school, with a challenging curriculum and an inflexible attendance office. We did occasionally pull the kids out of school for travel when they were younger, but falling behind in high school is not an option. Thus, we will not travel when school is in session. I’ll cross off the dates school is in session in red.


    Our younger daughters go to a sleepaway camp for much of the summer. This is the last year they are eligible to be campers and attendance is a priority for them. Thus, we will not travel when camp is in session. I’ll cross off the dates camp is in session, also in red.


At this point, we’ve got February break, April break, the end of August, and Christmas as possibilities for long family vacation, and possible long weekends in September, March, and Thanksgiving. In the past this would have made my planning fairly straightforward. However, in a big new wrinkle for our family, my oldest daughter will be heading off to college in the fall, which means our though process will be a little different this year.

After much discussion, we agreed that she can spend April vacation on a spring break trip with her friends. She also reminded me of an extracurricular commitment at the beginning of February break. My husband then reminded me of a work obligation at the end of February break and also pleaded that case that daughter #1 would not want to travel over Thanksgiving because it would be her first time back from college to see her high school friends. And my younger daughters reminded me that big sis would be off at school during September. I’ve put all these considerations in yellow on the calendar because most, but not all, of the family could travel then. I can see the harsh reality ahead that full family vacations are going to be few and far between, but I’m hanging on for now.

    Dates with partial family availability are shown in yellow.


Given all our obligations, our possible travel dates are pretty obvious. We have the chance of a full week in August or at Christmas, a long weekend possibility in March, and a mid-sized trip in February. I’ve marked our contenders in green.


Here’s where you need prioritize the vacation characteristics that are most important to you: weather, crowd level, price, attraction closures, availability of activities, and so on.

Let’s look at how these items change during our possible long travel weeks of mid/late August vs. late December.

  • Weather. I pull the monthly averages for Orlando on and see that the average high/lows for mid August are about 92/74 (ouch) and for late December are 73/52 (fine, but possibly chilly if temperatures are lower than normal). For us, this round goes to December.
  • Crowd Level. Here I need the TouringPlans Crowd Calendar. Our August dates show mostly 5 and 6 level crowds the first week (manageable) and 3 and 4 level during the second week (pretty good). Christmas week predictions for 2014 are not posted yet, but previous years have shown flat out 10s across the board (as crowded as crowded can be). The August wins this round.
  • Cost. There are many items that factor into the cost of your vacation, but one of the largest is the price of your hotel. To get a rough gauge on hotel price, I went to the Walt Disney World website and looked for the cost of a night at the deluxe-level Polynesian resort. I chose the Polynesian because we are a family of five, and the deluxe resorts allow five guests in one room. For the date of August 17, 2014, the website shows rates starting at $459 per night. For the date of December 22, the rate is $701 per night. While these are not necessarily exactly what your costs would be (particularly in August you might be able to find a better deal through a travel agent or a service like Expedia), they do give you a ballpark expenditure for your trip. August wins on price.
  • Attraction closures. We love almost everything at Walt Disney World, but there are a few rides that are must-dos on every trip (I’m talking to you Soarin’). I want to make sure that our favorite rides will be available during our vacation. I give a quick glance at the Attraction Refurbishment Schedule and see no notifications of significant closures during our possible travel dates. While there is a possibility that some rides will be down in August, this round is a draw.
  • Activities. These are the intangibles that can change the feel of your trip. My family will take into consideration that we love the water parks, which are best experienced in warmer weather. Win one for August. I am also enthralled by the holiday decorations at the parks. Nothing puts me in my happy place like the Osborne Lights at Disney’s Hollywood Studios. Big points for December, with the caveat that we have seen the lights several times in the past few years.

The Decision

With all the information in front of you and your priorities sorted out, it’s decision time. Some households may go by parental fiat, and others will take a poll and give everyone a vote. We hashed it out in a family conversation and decided that despite my husband’s aversion to heat, we will plan our big family trip for August. The main factors in our discussion were the lower pricing in August as well as some potential other plans that might become a priority in December. (Another Adventures by Disney trip is a distinct possibility!)

Fine Tuning

Once you know your time frame, it may pay to tinker with exact travel dates a bit. We travel to Walt Disney World by air. I plugged some different date combinations into Kayak, the airline price finder app, and found that flights from my area to Orlando vary by more 50 dollars a ticket during the weeks we’re looking at. If we leave New York a day later, we’ll save enough on airfare for a signature meal and some rockin’ souvenirs. Before you nail down your exact dates, it may pay to fine tune them with a bit of more in-depth research.

Look for Hidden Opportunities

I mentioned earlier that, in addition to a week-long Disney trip, we also like to take a long-weekend-sized trip to the World each year. Given my family’s current circumstances we’ll probably end up sneaking away for a few days in February. But in past years, those September dates have frequently been the winner.

The four-day September opportunity often presents itself to us because I happen to live in a community with a large Jewish population. School is closed then for the High Holy Days, making it a great getaway time for those not observing Rosh Hashana and Yom Kippur. When hunting for travel dates, look for these hidden opportunities. For example, New Jersey residents can often capitalize on a lengthy teacher conference in November (Jersey Week), Massachusetts residents may have a Patriot’s Day bonus, or Louisiana citizens may get free time around Mardi Gras. Keep an eye out for confluences of stealth time off. It may be possible to cobble together an entire week of vacation while only missing a day or two of school.

Ta Da!

In purple, are the dates when it works best for our entire family to be together at Walt Disney World next year. Once we laid everything out, it really wasn’t difficult to see what made the most sense for us.


While this process-of-elimination tactic can work for anyone, other guests will have different approaches. For example, my parents, a retired couple, have far fewer constraints on travel dates than I do. Their priority is to not encounter large crowds when they travel. For them, the first stop in their planning would be the Crowd Calendar. They might choose to redline any dates with a crowd level greater than five or six. Similarly, a family with medical issues exacerbated by heat might check the weather and then first redline the months of May through September, consulting their personal schedules from there.

What techniques do you use when planning your travel dates? What type of system works for you? Let us know in the comments below.

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Erin Foster

Erin Foster is an original member of the Walt Disney World Moms Panel (now PlanDisney), a regular contributor to, and co-author of The Unofficial Guide to Disney Cruise Line. She's been to WDW, DL, DL Paris, Hong Kong Disneyland, Aulani, DVC Vero Beach, and DVC Hilton Head. She's a Platinum DCL cruiser and veteran of 10 Adventures by Disney trips. Erin lives near New York City, where she can often be found indulging in her other obsession - Broadway theater.

7 thoughts on “Trip Planning 101: Deciding When to Visit Disney World

  • January 13, 2014 at 6:24 am

    Great advice! Love this and will definitely be using it on trips in the future!

  • January 13, 2014 at 9:16 am

    I would suggest that you look into buying points from Disney Vacation Club members. Visit the Disboards to see what’s available. 95% of the time you can buy points for about 50% off rack rates. I have done this on my last 10 trips, you do need your dates to be firm but it is a great savings and allows you to stay at the premium resorts

  • January 13, 2014 at 11:39 am

    Thanks, Erin. This is the detailed, well-researched and very well-written kind of post that makes your site worth the cost. I do so enjoy reading knowing the information has been vetted and presented with respect for your readers.

  • January 13, 2014 at 11:27 pm

    The process of elimination is great.

    But essentially, most people either go with or without kids,

    With… either in or out of school. Frankly,if you’re not taking out of school, then you should probably vacation elsewhere. Disney is very different and possibly unbearable during crowd levels during summer. And spring and Christmas are even worse.

    The best times are may, september, october, nov and dec except for thanksgiving and Christmas. Jan is to cold and so much is closed, and hours are very short. All other times are too crowded.

    So basically there’s may, food and wine, early Xmas, and Halloween. Bonus times are Jan or feb… pick one of those times and it will be a better experience. May being the wrist,but at least the water parks are open and fun.

  • January 14, 2014 at 12:26 pm

    Erin, has your daughter already selected her college?? (and therefore already know when her semester begins?) Here in the Midwest, most universities begin classes the third week of August, with freshman orientation the week before. Last fall we dropped our son off on August 10! Not sure how hypothetical your example is…

    • January 14, 2014 at 12:37 pm

      Thanks for looking out for me 🙂

      Yes, we are very fortunate that she was accepted to her first choice college early decision several weeks ago. Knowing that there is a huge variation on start dates, we held off much longer than usual with our travel plans for this year. (Very frustrating for this uber-planner.) The school she has chosen does not start until September.

    • January 15, 2014 at 8:05 pm

      Annie B, I totally concur. I’m a professor at a school in Texas and classes start the last week in August, and while there is some freshman orientation throughout the summer, there is a mandatory freshman orientation the week prior to the start of classes. I’d just make super-doubly sure that while classes don’t start until September, she isn’t required to be there prior to Labor Day.


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