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How to Plan a Multi-Generational Trip to Walt Disney World

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Multi-generational family vacations have been a ritual in my family for as long as I can remember. Our travels include my children and grandchildren, and quite often my mother too. Four generations sometimes traveling together. Three generations always traveling together. Where do we usually go? Well, Walt Disney World, of course! Several times a year three or four generations of us head to the most magical place on earth. When it comes to multi-generational travel there are really only two destinations that make it easy to plan – Walt Disney World or a Disney cruise. Disney makes it easy for all ages to have a wonderful and memorable vacation.


We are a Disney family for sure! It’s almost as if Disney is in our veins! At just a few months shy of his second birthday my grandson is getting ready for his fourth trip to Walt Disney World. After all, where else would he go for a haircut other than Harmony Barber Shop in the Magic Kingdom!

Walt Disney World is totally different from my youth, totally different than the Walt Disney World I took my kids to. Constantly changing and growing gives the entire family a chance to experience new things together. What other vacation destination can you visit that will entertain you, your children and grandchildren at the same time? There are so many choices at all the parks that we never have any trouble finding age-appropriate activities for everyone.

I try to take one big family vacation a year that four generations will be together. During the rest of the year, we visit in pieces – two generations here – three generations there – one generation alone. Over time, I have set a certain week each year for the four generation vacation so there is no longer a discussion of when to go. All family members know that the first week in June is family vacation week. Does that mean it always works out? No. This year, 2018, our family vacation lost half of the family members about 30 days before. Does that mean our vacation was ruined? No. Three generations went without them and sent them fun pictures and videos each day just to let them see (feel jealous) what they were missing.

Plan Early and Pre-Plan

Pre-planning is an important part of several generations traveling together. Know what each member of the family wants to do and anything special they may have on their wish list this trip. Have at least one family meeting to give everyone a chance to give you their ideas. Having a set week each year helps. If you don’t have a set family vacation week each year the first, and sometimes hardest part of planning is trying to coordinate the schedules of all the family members. Work, school, sports, camp and other commitments of each family unit becomes a thorn in the side of the organizer. The earlier the planning begins, the easier it becomes for everyone to make sure their schedule is clear.

After setting your dates, where will you go? If half of the family wants to go to Walt Disney World and the other half wants to go on a cruise ~ compromise! Go on a Disney Cruise!

If the decision is a hard one and there are five different vacation destinations that family members want to visit, you must come up with a plan that makes the decision easier. You can use any of the following methods:

  • One person (the organizer) is the final decision maker or tie breaker vote
  • Narrow down the choices to three and pop them all in a hat. The youngest family member gets to pick out the winning destination.
  • Everyone must attend (either in person or FaceTime or another method) family meeting for a family vote. 
  • Let the oldest family member (usually Grandma or Grandpa) make the decision

Finding a middle ground that makes everyone happy is sometimes hard but it helps to have on hand the most exciting and fun information about each destination that has been suggested.

Find Out Every Family Unit’s Budget

Each family unit has their own budgetary needs and the planning has to consider those budgets. What is each family willing to spend? If part of you can spend more (or less) are you willing to stay in different level resorts away from each other. Although this doesn’t make for an up-close family vacation, it does sometimes work better for allowing each family unit having their own space.

Accommodations are important when visiting Walt Disney World with several generations or with a large group. Each little family unit needs their own space. Depending on availability when I book I sometimes end up with 3 rooms (2 connecting and the third right next door). However, ideally I like to have a 2 or 3 bedroom unit with a kitchen so that we can at least have breakfast before heading to the park a few times during our stay.

I’m a firm believer in not allowing children from different family units to stay together in the same room. Each family unit has their own rules when it comes to nighttime and getting ready behavior. When groups of kids are together, it seems the rules are forgotten by those that have stricter rules at home than others do. Also keep in mind that Disney requires an adult be in each room at their resorts.

Will you have adjoining rooms, a villa, a vacation home? All of these must be answered before reservations can be made. If the group will be preparing breakfast in order to save some money, at least one family unit needs to reserve a resort offering a kitchen.

Be Sure There Is Something For Every Age Group

When planning meals, FastPasses and extra activities keep everyone in mind. Teenagers don’t want to do the same thing that toddlers want to so planning a multi-generational trip can be a challenge for keeping everyone happy. Make sure there are activities and amenities for everyone. 


I try to make at least one reservation per trip for my son and his wife to have dinner alone for a date night. This also gives me the opportunity to have a fun night with my grandchildren! I always include Chef Mickey’s for my grandchildren. We are slowly working our way through each restaurant in Epcot to expose the kids to different varieties and nationalities of food. Keep in mind that as a large group you don’t have to eat every meal together. It is often harder to get a reservation for 10 so there is no harm in 5 of you eating dinner at Be Our Guest while 5 of you eat dinner at Cinderella’s Royal Table and then meeting up afterwards for ice cream.

Plan a Park Free Day

This gives everyone in the group a chance to go off and do whatever they choose – even if it’s the entire group swimming in the resort pool together!

Split Up/Stay Together

There are times everyone will want to stay together. After all, everyone wants to see the little ones get excited about a parade or a character. There are also times that two of you may want to head to Space Mountain while three others may want to go on the Carousel of Progress. Flexibility is crucial when three or four generations travel together. Just always be sure to set a clear meeting point and time.

Memory Maker

Memory Maker is super important for a multi-generational trip. Everyone wants to be in the picture. No one wants to be left out when they have to be the one taking the photos. Memory Maker to the rescue!

Add Some Extra Magic

I also try to add something extra. One trip I had my granddaughter proclaimed a princess during breakfast in Akershus Royal Banquet Hall in the Norway Pavilion. You can do this through Disney Floral and Gifts – I included all the information in a post afterwards – My Storybook Moment – Princess – From Disney Floral and GiftsOn another trip, I reserved a specialty cruise just for my family! It was a wonderful experience – Our Wishes Specialty Cruise was More Fun Than I Ever Imagined! It was actually so much fun, we are making it a tradition!