Planning your first Walt Disney World trip with little kids (and maybe even grandparents tagging along)? Welcome to the most exciting—and sometimes overwhelming—phase of your Disney adventure! One of the biggest questions I hear from families is: “Okay, but when should we actually go?”
It’s a great question because picking the right time to visit can make or break your experience, especially when you’re juggling preschoolers’ nap schedules and grandma’s comfort. Let’s break it down so you can avoid the crowds, beat the heat, and still experience plenty of magic.
Best Months to Visit Disney World: Avoiding the Madness
If you can swing it, aim for late January through early March or late September through early November. Why? Cooler Florida weather and manageable crowd sizes. Think: fewer lines, shorter waits, and more chances to snag those all-important character hugs without your preschooler turning into a cranky pumpkin.
Disney World Dates to Steer Clear Of (Unless You Like Crowds, That Is)
Steer clear of peak holiday seasons, spring break, and summer vacation periods. I’m talking Easter, Christmas, Thanksgiving week, and the holy grail—summer months. The parks turn into a human sea. Trust me, when you’re chasing little feet through throngs of people, the magic can get a little… well, overwhelming.
The Magical Exceptions: Special Events
If your family digs the holiday spirit, visiting during Mickey’s Not-So-Scary Halloween Party or Christmas celebrations can feel like stepping into a storybook. But heads up—these times bring heavier crowds, and prices tend to climb. So pack your patience, and maybe schedule some mid-day pool breaks!
Disney Weather Real Talk
Florida weather can be unpredictable. Even in “cooler” months, afternoon rain showers pop up like clockwork. Pack lightweight rain ponchos (the kind you can fold into a pocket or an umbrella-my choice), and plan your outdoor adventures for mornings and evenings whenever possible. Also, lather on the sunscreen—little ones’ skin needs love and protection. Don’t forget to add sun protection for your lips as well.
For the record, we are umbrella people. We do not like having a sticky piece of plastic to carry around all day. I LOVE having a small micro SPF umbrella for each person on hand. This is assuming the person using it can carry it…if not, please have ponchos on-hand to cover storllers, scooters and belongings.
Final Tip: Listen to Your Family
At the end of the day, the “best time” to visit is when your family can relax and enjoy. Preschoolers and grandparents alike thrive on routine, so if your ideal dates line up with school holidays or necessary family schedules, it’s okay! Just know there are ways to make it work, and we’re here to help you tailor your plans to fit.
For the record, we are umbrella people. We do not like having a sticky piece of plastic to carry around all day. I LOVE having a small micro SPF umbrella for each person on hand. This is assuming the person using it can carry it…if not, please have ponchos on-hand to cover storllers, scooters and belongings. Tip: Your Disney Resort Hotel usually has towels out in before you exit for the bus, take one or two, if they are out, that means rain is coming.
Curious about how many days you should plan or which tickets make sense for your crew? Stay tuned for the next post where we’ll dive into that—and if you want to skip the wait, reach out any time at letstravel@thewdwguru.com. Planning Disney vacations is what we do best!
Ready to get started? Download my free “Ultimate WDW Planning Checklist for Families” and start organizing your dream trip today!
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