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Countdown to Disney: Planning a Multigenerational Trip To Disney World


In case you missed it, The Glover Family is headed to Disney World! You can follow along in all the planning in our Countdown to Disney series! Missed the reveal? You can view it here: Surprise, You’re Going to Disney World!

Resident Disney Expert

When Stephanie mentioned that her family *may* be planning a Disney trip with her parents and sister’s family I was stoked for them. Especially since I know Stephanie hasn’t been since she was younger and her kiddos have never been. With this excitement for her family came a lot of questions. That’s when I stepped in as “resident expert” for all things Disney!

I guess you can say that Disney runs in my blood. We have quite a history, one that I’m proud of. From visiting as often as we could as a family growing up, being a WDW College Program graduate of 2002, and even having a fairytale wedding in the Wedding Pavilion in 2007 – I like to think that I’m qualified to share stories, planning tips, and a little bit of Disney magic.

Our family just enjoyed our family vacation this fall and for 5 days of that it was a multi-generational trip. There’s something to be said about experiencing the Disney magic in your child’s eyes while they are experiencing it with their grandparents. Those nostalgic memories of visiting as a child have nothing on the new ones that were recently created.

Grandparents enjoying a walk down Main Street in Walt Disney World.
For some Disney can be extremely overwhelming, expensive, and in turn intimidating to plan. It doesn’t have to be! We are here to help. Having been on a few of these family trips here are 4 Tips on planning a MAGICAL multi-generation Disney trip.

Top Tips From Our Last Trip

1. Plan but don’t be too structured. We are big advocates of having a general idea of some goals for your trip. You don’t have to get all Danny Tanner with a “clipboard of fun” having a minute-by-minute itinerary. Let loose, go crazy!


Your vacation goals can be as simple as everyone choosing an attraction, show, or character that they would love to experience. In our family it was a mixed list.

Abigail wanted to ride Seven Dwarfs Mine Train, Riley wanted to ride the People Mover, Mommy wanted the family to meet Mickey in Town Square Theater at the Magic Kingdom, Gigi wanted to see the girls experience the new Frozen ride in Norway, Daddy and Poppy wanted to see the girls faces as they see the castle for the first time, Aunt Britt wanted to ride the new Soarin’, and Uncle Chris wanted to try the new Test Track.

Countdown to Disney: Family fun on the Seven Dwarves Mine Train in the Magic Kingdom in Walt Disney World.

Yes, we had 8 people, but we were there long enough to experience all of those things. Knowing ahead of time what experiences were on everyone’s “wish list” helped to ensure that everyone was able to experience the magic they were hoping for.

2. Take a break! You don’t have to spend every moment with one another. Yes, the trip is all about spending time together as a family – but sometimes families need to take a little break now and again.

You may think that you can totally be a Park Commando, 4 Parks in 1 day, and all that. In reality, depending on what time of year you go you may be surprised – what you may think could be a slow day could turn out to be one of the hottest days of your trip with too many people around. When you notice a bit of the crank pants coming on consider going back to the hotel and taking a nap, taking a dip in the pool, or just a change in some scenery.


3. Let them lead. If you want to be surprised, plan a day where there are no plans and let the kiddos take the lead. Let them decide where to go, what to ride, where to eat. See where the day takes them. This may not necessarily be a good idea for kiddos that don’t like that type of responsibility or pressure, and if that’s the case maybe try a moment, an hour – it could be as simple as saying “we are going to stay at the hotel this morning, pick some fun things you would like to do.”


4. Plan a Park Free Day! Don’t underestimate planning a day away from the parks! Did you know that Disney’s resorts offer various activities throughout the day?

For example, at Disney’s Art of Animation Resort they have activities planned most days. Like their legendary Pool Parties – featuring music, awesome activities, and games such as bingo, poolside challenges, party games, and trivia.

They even have a character artist that meets at 11, 2, and 5 in the children’s play room next to the Front Desk that shows anyone how to draw your favorite Disney Characters. Other fun activities include bike rentals and “Movies Under The Stars” at 7pm.


Get Ready for the Ride of Your Life

Like I said, Disney is not for the faint of heart. You do have to find the fine balance between planning everything out and allowing some elements of surprise and spontaneity. There is so many resources out there to help you plan the vacation of a lifetime with all the magic that Walt Disney World Resort has to offer.

Here are some sites that we love to use while planning, check them out before our next post.

We cannot wait to bring you more tips, tricks, and magic! Up next: Countdown to Disney: Optimize Timing for a Grand Plan



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