Once upon a time, a Disney trip meant parents taking their kids to enjoy the magic while grandparents stayed behind. But times have changed, more than 50 percent of families now travel with both children and grandparents, according to the Family Travel Association’s 2023 survey.
Recently, my husband, our 16 year old son, two cousins, and even Grandma and Grandpa set out on a four day, three night magical adventure to Walt Disney World. With iconic rides, family-friendly meals, and entertainment for all ages, Disney is the perfect destination for a multi-generational trip. However, planning for everyone from grandparents to teens takes some strategy. Here’s how we made it work!
1. Best Timing for Kids, Parents and Grandparents
The best time to visit Disney with grandparents and kids is between late October and May when the weather is cooler, and crowds are smaller. If you must visit during peak times, don’t stress, longer park hours and extra entertainment make up for it.
A slower pace is key for multi-generational travel. I recommend at least two park days, with a rest day in between to recharge. If you are flying in on an early flight, use the first day as a recovery day to avoid exhaustion. We also opted for a Park Hopper Pass, allowing us to move between parks at our own pace.
2. Staying on Disney Property is a Game Changer
Staying on Disney property made all the difference for our trip. We booked two Lion King Suites at Art of Animation Resort, which gave us plenty of space; two bathrooms, and a living area with a pull-out sofa bed. The suite’s kitchenette complete with a Murphy bed that pulled down from the wall made it easy to relax and refuel.
Resorts like Art of Animation, Polynesian, and Riviera Resort offer quick access to the parks via the Monorail or Skyliner, cutting down on walking. Speaking of the Skyliner – it might just be my favorite attraction! It’s such a relaxing way to travel and super convenient for strollers and scooters.
3. Wear Matching T-Shirts & Assign Buddies
Matching shirts aren’t just for Instagram, they actually helped keep our group together! Custom shirts are an affordable, fun way to keep an eye on each other. Also, assigning buddies (especially for younger kids) helps ensure no one gets lost in the crowd.
Pro tip: Ask any Cast Member for a FREE celebration button if you are celebrating your first visit, birthday, or anniversary!
4. Strollers & Scooters are Lifesavers
Disney World is huge, we are talking at least 15 miles of walking per day! When Grandpa Angelo arrived in his dress shoes, I realized I had forgotten to tell him to bring sneakers. We quickly rented a wheelchair and scooter for the grandparents, which turned out to be a game changer.
Wheelchairs are just $12 per day, and Disney allows you to transfer rentals between parks for free. Just show your receipt at the next park and you’ll get another one at no extra charge. Plus, the kids loved taking turns pushing Grandma around!
5. Best Character Meals for The Whole Family
A quick monorail ride from Magic Kingdom took us to Chef Mickey’s at Disney’s Contemporary Resort, where we had brunch with Mickey, Goofy and Pluto and the best cinnamon rolls ever!
For a fun dinner, we dined at The Crystal Palace in Magic Kingdom, where we met Winnie the Pooh and friends. I love this restaurant because of the views of Main Street U.S.A. and of Cinderella’s Castle. We booked a 6pm reservation so we could step outside just in time for the Happily Ever After fireworks. Watching my husband, our son and Grandpa three in a row, all shed a tear as Tinker Bell flew across the sky was a priceless memory.
6. Ride and Attractions for Everyone
Our group was split between thrill seekers who enjoyed attractions like The Guardians of the Galaxy: Cosmic Rewind Attraction and those who preferred more relaxing attractions. Some of our favorite family rides included:
– Haunted Mansion
– The Many Adventures of Winnie the Pooh
– Pirates of the Caribbean
– People Mover
– Peter Pan’s Flight
– Mickey & Minnie’s Runaway Railway (and my absolute favorite!)
7. Family Dance Party with Disney Characters
At Hollywood Studios, we escaped the rain by catching Disney Jr. Play and Dance!, which is a live show that runs multiple times a day. A DJ played upbeat Disney hits, and we had a blast dancing together as a family with some of our favorite characters. Best of all, we got to take pictures with Roadster Mickey Mouse!
8. Interactive Shows & Dinners for Everyone
Some of our best family moments happened over dinner. On our first night, we dined at 50’s Prime Time Café in Hollywood Studios, where the servers called us “cousin” and playfully enforced old-school family rules.
Another night, we went to Hoop-Dee-Doo Musical Revue at Wilderness Lodge, where we enjoyed all-you-can-eat barbecue and live entertainment. Grandma Anita even got serenaded for her birthday! Afterward, we roasted marshmallows at the Chip & Dale Campfire Sing-Along, a perfect way to end the evening with Grandpa saying, “This is the first marshmallow, I’ve roasted in 72 years!”
Make Your Own Magical Memories!
This trip created some of our most cherished family memories. Whether you’re planning your first multi-generational Disney trip or your tenth, these tips will help make it smooth, stress free and magical for everyone.
So grab your Mickey ears and start planning – it’s time for your own Disney Adventure!
***Disclosure: The writer and her family were hosted by Disney.
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