Planning a Multi-Generational Trip to Disney: Making Magic for Everyone

Family photo in front of Cinderella's castle in Magic Kingdom in Disney World

The Magic & the Reality

Let’s be honest; taking a Disney vacation with the extended family sounds awesome. The first grandchild in the family (AKA, Skippy) gets to boop Pluto’s nose at a character meeting while Grandma and Grandpa get to see? Amazing. Absolutely magical. The reality of a multi-generational Disney trip, however, is that there’s a A LOT of moving pieces. Everyone’s got a different bedtime. Energy levels range from toddler to grandparent levels. Think everyone wants to eat at the same quick service? Guess again.

Photo of Liz, Nicole, Skippy, and Pluto in EPCOT

A multi-generational Disney trip isn’t just a vacation. It’s a logistical operation. My wife and I recently planned and executed (pretty flawlessly??) a multi-generational trip to Disney World with her parents and aunt, ourselves, and our toddler. You can benefit from our wins and fails through our experience.

This guide is to help you plan a trip where nobody feels left behind and everyone gets their Disney magic.

The Divide and Conquer Philosophy

Look, it may seem tempting and maybe extra magical to do everything together. Rope dropping together, waiting in lines together, etc. This can, however, quickly lead to burnout. Remember that you’re juggling a bunch of different interests and energy levels. While we were happy to hang out in the long, albeit super cute line for Peter Pan’s Flight, my in-laws were starting to lose steam.

Photo of a painting with Peter Pan in the queue for Peter Pan's Fantasy Flight.

Give yourselves permission to split up. Of course, there are going to be rides and events that everybody wants to take part in. Family breakfast together at the Crystal Palace? Absolutely. Everybody meets up to watch Belle’s Enchanted Tales together? 100%. If youf father-in-law really doesn’t care for the coaster-type rides, give him license to go grab a turkey leg instead. Everybody wins.

With the divide and conquer philosophy, I strongly recommend designating someone as the “captain” or lead planner. For our vacation, that was me (Liz). I was in charge of dining reservations, Lightening Lanes, and creating the general itinerary each day. While it’s a little bit of a thankless and repetitive task, (“Wait, what are we doing now?”), it’s an important job! The lead planner can really be the make or break between chaos and making your dinner reservation at O’hana.

Choosing Your Home Base: Best Resorts for Multi-Generational Groups

As the home base will most likely be where the whole family is staying, this choice is important and there are a lot of considerations to be made. For us, 1) budget and 2) transportation were of utmost priority.

Disney Vacation Club (DVC) Villas

If your budget allows, DVC villas tend to be the highest rated option. These are spaces with full kitchen and laundry, and separate bedrooms for privacy. There are DVC spaces available at most of the deluxe resorts including:

Each of these options come with their own unique, aesthetic vibes and offerings. For instance, if your family is more into beach vibes, the Beach Club or Boardwalk might be more appropriate. If you’ve got littles that are super into animals, the Animal Kingdom Lodge might make more sense.

Suite Life

The most budget-friendly option would be getting a suite at the Art of Animation. You have your option between Cars, The Lion King, or Finding Nemo suite. Each suite sleeps 6 adults with 2 full bathrooms. As a fun fact, when planning our own multi-generational trip, we were planning on getting a Lion King suite. We showed my in-laws a video walk-through of one of the rooms, and my father-in-law could not be sold on the Murphy beds. Despite trying to explain to him that it would be fine and that all rooms have Murphy beds (they do at the budget resorts), he was not having it. So we all paid a little more (yes, more) money to get adjoining rooms at Pop Century.

Important tip if you do this: request adjoining or close rooms upon booking! Otherwise, Disney can’t guarantee your rooms will be close and/or adjoining.

The joke was on my father-in-law when we rolled up and he realized one of the beds in his room was indeed a Murphy bed. It turned out fine, but goodness! I do wish we had put up a little more of a fight. If only to be closer to the adorable Finding Nemo splash pad at the Art of Animation!

Finding Nemo structure at the splash pad at the Art of Animation Resort.

While this is the only experience we can attest do, it was great. Paying a little more for either Pop or AoA as opposed to the All Starts hotels gave us access to the Skyliner. In fact, we now feel like Pop Century is the best value resort at Disney. With Skippy, any opportunity to NOT take them out of the stroller (and in this case, it was on journeys to not 1, but 2 parks) was amazing. We also felt the aesthetics of both Pop and AoA were much more dynamic than the All Stars hotels.

Logistics-First Resorts for Multi-Generational Groups

As alluded too; in planning your home base, budget isn’t the only consideration. For us, right next to budget is logistics. How are we getting from the resort to the parks? If you’re staying at the All Stars, that’s all buses all the time. If you’re following a logistics-first strategy, you want to consider which park(s) you’re going to frequent the most. At Disney World, there’s no resort that, for example, will whisk you off to whichever park of your choosing in a “magical” way.  

Monorail Resorts

Arguably, a monorail resort is ideal is if you have littles. Monorail access to Magic Kingdom and EPCOT means you can roll the stroller right into the monorail car; no breakdown required. That means you’re only taking other transportation options when you visit Hollywood Studios and Animal Kingdom. The monorail access can also make a mid-day nap pretty seamless. You can catch the monorail back to the resort after a half-day in Magic Kingdom and your little even has the chance to fall asleep on the way.

Inside of the Gold Monorail car at Disney World.

To get to the other parks, Hollywood Studios and Animal Kingdom, you would use the Disney bus service.

Skyliner Resorts

Skyliner resorts offer a similar benefit as the monorail at a lower price point. You’re also swapping out a stop at Magic Kingdom for one at Hollywood Studios.

Important Note: Double-wide strollers do need to be collapsed when boarding the Skyliner. So if you’ve got two littles riding side-by-side, you would lose this particular perk of a Skyliner resort.

If this helps inform your decision, I can also share the Skyliner was Skippy’s favorite ride at Disney at their first trip. They sat in the stroller laughing like crazy every time one of the Skyliner gondolas going in the opposite direction passed us by. Guess you had to be there?

The Disney Skyliner from the Art of Animation side.

To get to the other parks, Magic Kingdom and Animal Kingdom, you would use the Disney bus service.

Water Transportation Resorts (Ferries & Water Taxis)

Magic Kingdom Resort Area
EPCOT & Hollywood Studios Area
Disney Springs

If hopping on a monorail or flying through the sky don’t sound appealing, water transportation options might be worth considering. These options will vary depending on the resort that you’re staying at. Most of these options will require a more flexible budget as all of the above hotels are either moderate or deluxe value resorts.

On Foot Resorts

While my wife and might be in the minority on this one, but we LOVE being able to walk to one or more of the parks. A couple of years ago, I was lucky enough to attend a work conference in Orlando at the Disney Dolphin hotel. Rest assured, we spent the off day at Disney World and did you know you can literally walk from the any of the above resorts to both EPCOT and Hollywood Studios? EPCOT is a much closer walk, but Hollywood Studios is maybe another 15 minutes.

Like I said, we might be in the minority because a Disney vacation is 85% walking, but we absolutely loved just being able to leave EPCOT and walk back to our hotel room. No waiting in the queue for the next bus/gondola/monorail.

Off-Property vs. On-Property

While deciding what your home-base is for your multi-generational vacation, you’ll likely debate between staying off-property or on-property. There are distinct pros and cons for both:

Off-property

On-property

In all honesty, we have never stayed off property for a Disney vacation. While it may be cheaper, we think the kicker for us would be missing complementary transportation. Especially with Skippy, we would need a car seat and likely need to rent a car. And with that would come the need to park at each of the parks. We feel it’s (at least currently) worth the cost to not have to lug a car seat through the airport down the East coast.

For a multi-generational family though, an off-property stay could be amazing. You could rent a house with a full kitchen, enough bedrooms for everyone to have their own, and in-house laundry machines. If you play your cards right, this could mean having breakfast at “home” before heading to the parks, which would be even more cost savings. Off-property locations would also offer more opportunity for family time. Depending on the set-up of an on-property stay, it might still feel like the family is still very much separated. Sharing a rented home can feel a little more familiar and comfortable, which might be super beneficial if traveling with family you don’t get to see very often.

Food for thought though; there’s no right/wrong answer. It’s about you, your family, and your vacation goals.

Logistics for Every Speed: Strollers, ECVs, & Walking

A vacation to Disney World is:

With all that moving and standing, you’ll want a plan for everyone in your multigenerational planning. Infants and toddlers (and even beyond!) will need strollers, and you may have some folks in your group would benefit from an EVC, or Electric Conveyance Vehicle.

Toddler Perspective

If you consult the Disney blog-o-sphere, you’ll likely conclude that a stroller is non-negotiable. Skippy wasn’t quite walking for their first Disney, so we definitely needed a stroller. Strollers are essential if you have a little who still takes a nap as well. Skippy is a terrible napper and NEVER naps in the stroller, but at Disney World (AKA over-stimulation station), they took stroller naps. Not amazing ones, but enough to get us through the long park days. When it comes to stroller planning, there are three options.

Bring Your Own

The first, cheapest, and most obvious strategy is to bring your own. This one’s great because you know exactly what you’re getting. Most all, if not every, airline will allow you to gate check one stroller and one car seat free of charge per child. If you’re bringing your own stroller, keep the following things in mind:

Rent a Stroller

Alternatively, you may want to rent a stroller. This can be preferable if you don’t want to travel with your stroller or if the stroller you have wouldn’t work for your Disney needs. For example, most kids transition out of their stroller around 3 or 4 years old. A Disney vacation pushes kids upwards of 7 or 8 with demands to stay on their feet. You might want to rent a single or double (if you have a little and a bigger kid) stroller to accommodate one or both kids. If you’re renting a stroller, keep the following things in mind:

Buy One When You Get to Orlando

This one might be a little controversial. Why buy a stroller when you get to Disney? Wouldn’t you then need to bring it home? Nope. This strategy would be best if you have one or more kids who have outgrown their stroller at home, but aren’t quite up to the challenge of walking ALL day. You would buy a cheapo ($30-$50) stroller off of Amazon and have it delivered to your room at the resort or offsite property. It’s cheaper than a rental, and when you’re done you have the special bonus of leaving the stroller behind to “pixie dust” future guests who might need it! If you’re buying a cheap stroller, keep the following things in mind:

The Grandparent Perspective

On the other end of the multi-generational family spectrum, we have the grandparents. This might also include family or friends who might benefit from some mobility assistance. For this, there’s the option to rent an ECV. This post has already emphasized just how much walking a person does at Disney World. 10+ miles a day! In addition to this option, it’s good to be aware of hidden seating areas for some quality rest (and people watching!) in each of the parks.

ECV & Wheelchair Rentals

At each of the Disney parks, you have the option to rent an ECV vehicle or wheelchair. ECVs are motorized scooters. Each park offers rentals with a per-day cost. If there are members in your planning party that are on the fence about whether they need to rent an ECV, definitely remind them that:

Hidden Seating

If anyone in your multi-generational group just wants a breather, there are a ton of hidden seating areas scattered through each park.

Magic Kingdom
Hollywood Studios
EPCOT
Animal Kingdom

Dining for a Crowd: Best Dining Options for a Big Group

Deciding where and what to eat for a big, multi-generational group can be challenging. Here, we’ve outlined some suggestions and tips that worked really well for us.

Booking Strategy

For those staying on-property, you’re able to book table service reservations 60-days out from your check-in day. That means that 60-days before the day you check-in, you can book your dining reservations for your whole vacation. This is key if you hope to snag some of the more popular spots like brunch at O’hana or dinner at Cinderella’s Royal Table.

When you’re on vacation with a big, multi-generational group, you’ll want to link “Family & Friends” before you reservation booking date. This will allow one person to make big, group reservations for everyone.

Best Restaurant Types for Large Groups

We recommend dining options that offer a buffet/family style and/or entertainment. Ticking either, or both, of these boxes can help ensure that everyone in the group has a great time regardless of their food preferences. While my wife and I, and Skippy, to a degree, are adventurous eaters, we were traveling with several “meat and potatoes” kind of people. It was really important that everyone’s taste buds were taken into account. It’s everyone’s vacation, after all!

Buffet/Family Style Options at Walt Disney World

Touring Plans: A Day in the Life (By Age)

Park days on Walt Disney World vacation with a multi-generational group is no joke! There’s a lot of different levels of interests and energy to tend to. And you want everyone to have a magical time because it’s everyone’s vacation! We suggest some general itineraries to address the unique situations everyone in the group might be tending to. Remember, don’t be shy about spitting up! It’s not a class field trip. If two people want to go ride Pirates of the Caribbean while everyone else wants to get in line for Space Mountain, have at it. Everyone can meet up afterward for some Mickey ice cream bars in front of the castle!

Toddler Focus

We feel like planning a day around your toddler(s) or smaller children really means splitting the day into two parts. Pre-nap and post-nap. Magic Kingdom has the highest number of rides for littles, so that’s the park choice. Playing in both Fantasyland (Peter Pan’s Flight, Many Adventures of Winnie the Pooh, etc.) and Adventureland (Pirates of the Caribbean, etc.) can spark their imagination. Then, around 1PM and 2PM you can prioritize nap time. If you’re staying at one of the Monorail resorts, you can hop on the monorail to a mid-day nap and wind-down. Then around 4 o’clock you can head back to the parks for more fun and fireworks before turning in for the day. Fun!

Winnie the Pooh covered in the Many Adventures of Winnie the Pooh ride in Magic Kingdom. Emphasis on the toddler when planning a multi-generational Disney trip.

Grandparent Focus

The name of the game is “exploration” for the grandparents in the group. We’d suggest EPCOT or Animal Kingdom might be the best parks for grandparents. Both offer lots of spread out walking and interesting things to look at and experience. Each country in EPCOT has performances that showcase many of the world’s cultures, and most (if not all?) are located inside (i.e. air conditioning). Animal Kingdom has several fun shows like the new Zootopia: Better Together and Finding Nemo: The Big Blue…and Beyond. Great ways to sit down and break up the time otherwise spent exploring all the parks have to offer!

Thrill Seeker Focus

While we wouldn’t go as far as to claim that Disney World has any “thrill” rides, but there are some that are more intense than others. More importantly, there are a bunch of rides toddler and littles cannot ride due to height requirements. Multi-generational groups are great for this kind of itinerary planning because there is almost always someone in the group who is happy to hang with the littles while some of the big kids (AKA, Disney adults) go and ride Guardians of the Galaxy: Cosmic Remind or Rise of the Resistance. My father-in-law, for example, is not a fan of fast rides or drops, so he hung out with Skippy when the rest of the group wanted to ride Space Mountain.

Liz and Nicole's ride photo on Guardian's of the Galaxy Cosmic Rewind. Emphasis on the thrill seekers when planning a multi-generational Disney trip

Alternately, if he were a fan of these rides, we could have participated in the rider switch. Many rides at Disney World offer this option, and the specific way you do rider switch differs from ride to ride. At Rise of Resistance, for example, we went to the front of the queue and they advised us to have our whole party come over. They asked us who would be riding first and who would be hanging out with Skippy. My wife and I said we would ride first, and then my mother-in-law and father-in-law (who were both waiting with Skippy) each got issued a Lightening Line to use on Rise of the Resistance when we finished riding first. Neat, right??

Here are all the rides that offer rider switch at Disney World:

Magic Kingdom Park

EPCOT

Disney’s Hollywood Studios

Disney’s Animal Kingdom Park

Shared Joy

Disney World is really made for something like a multi-generational trip because there are so many opportunities to hit a sweet spot that appeals to toddlers, grandparents, and everyone in between! These are the rides that offer low impact, but high “Disney magic.” If the group is taking advantage of our suggestion to split up when folks want to do different things, we recommend coming back together to enjoy these attractions together.

Magic Kingdom

EPCOT

Hollywood Studios & Animal Kingdom

Managing the “Human Elements” (Energy & Emotions)

With so many moving parts in a multi-generational Disney World trip, there are a lot of “human elements” to tend to. While one can’t possibly expect every little hiccup that might pop up, there are many that you can anticipate. We reflected and came up with four different challenges and suggestions on how you might address them.

Hydration & Heat

Summer vacations in Florida are HOT. Our last trip was in November, the week before Thanksgiving, and it still got up to 85* a couple of the days we were there. Make sure everyone in the group has sunscreen (or is at least reminded about sunscreen of they’re big kids (AKA Disney adults). Either bring your own water bottles or take advantage of the free cups of ice water at all of the Quick Service locations. You can check out our post on why we actually decided to never bring our own water bottles again and to stick with these free cups!

The “Disney Wall”

Remember that as magical as Disney World is, it’s over-stimulation station. You’ll know your toddlers and littles best, but you want to keep eyes out for when they might be getting over-stimulated and hopefully address the accompanying meltdown before it happens. Due to the pretty constant stimulation, you might find your otherwise pretty content toddler to be more prone to a meltdown. As such, you’ll want to take into account that it’s not an average day for them, and you might need to be a little diligent in helping them find ways to emotionally or physically regulate when they need.

Budgeting Talk

On a multi-generational Disney World trip, the question of who pays for what might come up a lot. In our experience, this tended to come up the most when it came to food. We’d finish up a Table Service meal and everyone played the credit card dance. Going in, my wife and I discussed this very real concern months before our trip. I mapped out the budget for everyone and actually suggested we all use Disney gift cards for food and souvenirs. We use the widely suggested strategy of using the Target Red card to purchase Disney gift cards from Target. Using the Red card automatically takes 5% off. That means a $100 gift card only costs $95. While it might not seem like a lot, you can use this strategy to book your entire Disney trip which can add up to some decent $$$ savings.

Despite this strategy, I will admit there were several moments during our trip when Skippy eyed a souvenir and grandma and/or grandpa SWOOPED in to buy it. You pick your battles, for sure! Skippy zeroed on on this Roo plush coming out of the Many Adventures of Winnie the Pooh and Grandpa was ON IT. (Skippy still sleeps with Roo every night!)

Capturing Memories

After a Disney trip, one of the absolute best experiences is looking through photos from your trip. The silly faces, the magical moments – all of it! When planning a multi-generational Disney World trip, we cannot stress enough just how strongly we recommend purchasing the Memory Maker.

The Memory Maker is an all-inclusive package that includes all of the photos taken of you and your family on the Disney rides and PhotoPass photographers. PhotoPass photographers are stationed all around each of the parks at all of the iconic photo spots (i.e. the castle in Magic Kingdom and the Tree of Life in Animal Kingdom). Purchasing the Memory Maker gives you access to every single photo taken by these photographers. While the cost is an investment at a couple hundred dollars, with a multi-generational group going, you can split the cost across family members. That way, everyone gets ALL the photos for a fraction of the cost. Yay!

Conclusion: The Legacy of the Trip

While a multi-generational trip is A LOT, it’s well worth it. Definitely be mindful about picking your home base and meals. You know your family best. If planning gets stressful, or if you find yourself in Magic Kingdom on a particularly busy day, keep in mind that you won’t remember the lines; you’ll remember the smiles.