Traveling to Disney World with Friends or Extended Family: Good Idea or Bad Idea?

You’re planning a super fun Walt Disney World vacation! Your sister-in-law hears this and thinks a Disney vacation sounds super fun too.

And she wants her family to travel with you. Yayyyyy!!!

Yayyyy????

If you have enough conversations about your Disney World trips, inevitably your in-laws, or sister, or your college roommate, or your next door neighbor will come up with the brilliant idea that if you’re both going to have amazing Disney vacations, then wouldn’t it be great to have those vacations together.

Is that a good idea or a bad idea? As with most things Disney, the answer is, “It depends.” Traveling with friends or extended family could be a wonderful experience for all involved, or it could be a way to beat a perfectly nice relationship to death with a grotesquely oversized turkey leg. It’s important to look closely at what traveling with others really means and do an honest assessment of whether it makes sense for you.

Here are some things to think about:

• Can the people you’re traveling with follow rules? During the Coronavirus pandemic, there are lots of rules. Wear your mask, keep social distance, sanitize often. If you know that your prospective travel companions are rule flaunters in general, then now is not the time to travel with them.
• Do you actually like these people? All of them? Sure you love your sister like, well, a sister, but what about her overbearing husband or her bratty daughter? While you may be able to cope with these folks at a two-hour birthday party, will you actually remain sane if you have to listen to bro-in-law complain about his boss for five straight days of your precious vacation time. If you can’t honestly say that you enjoy spending time with every single person in the other family, then reconsider making the trip.
• Do your kids actually like each other? Up until age seven or eight you can usually throw youngsters together and they’ll find a way to make it work. But once the kiddos get their own interests, all bets are off. Does a cheerleader cousin make your goth daughter’s skin crawl? Will throwing your children together with polar opposites ruin their vacation (and thus yours)?
• Do you have a similar financial situation? This may be difficult to assess, because most folks in the US would rather sleep on hot coals than have an honest discussion about money. Despite the discomfort, you’ve got to have the money talk before embarking on a vacation with someone. Do your friends think a vacation only a vacation if you’re staying in a five-star resort, while you’re clipping coupons to splurge on a moderate hotel? Do you want to eat table service for every meal, while your friends want to save their pennies by making oatmeal in the room for breakfast and bringing granola bars for snacks in the parks? Obviously, neither approach is right or wrong, but if you’re not on the same page then resentment is bound to happen. The “haves” will feel like they’re being held back. The “have nots” will feel over-extended or guilty. If your spending ability and philosophies are not in sync, save your socializing for your home turf.
• Are your bravery levels compatible? There are plenty of situations at the Disney parks which challenge the senses. Will you react to them in the same way as your companions? If they want to do Expedition Everest six times in a row, while you get dizzy during the rotations at Carousel of Progress, then resentment is likely to accumulate while one group cools their heels waiting for the other.
• Do you have similar attitudes about time? Are you always early for reservations while your bestie is often later than fashionably late? Are you ready for rope drop and pooped by 8:00 pm, while your in-laws like to sleep until noon? It’s difficult to have a great time with someone if you’re never awake at the same time or if you don’t have the same attitude about promptness.
• Do you discipline the same way? In some families, the rules are the rules, no matter where you are. In other families, vacations are where rules are made to be broken. If one set of kids in having ice cream for breakfast, while the other gets no dessert unless they finish their green beans, tensions will arise.
• Do you have similar opinions about COVID risk management? Alas, COVID is still a risk with any Disney World vacation. If you still believe in testing at the first sign of trouble, do they feel the same way? What will happen if someone gets sick? Make sure that people you might spend time with have the same protection philosophy that you do.

Even if you’re truly BFFs at home, it’s important to think about the ways in which travel will put different stresses on the relationship. Daytime and nighttime routines can be very different. Unknown stimuli (such as overstimulation in a theme park) can cause perfectly balanced relationships to skew. Do you really want to mess with a great relationship now? Or ever?

Now before you start thinking that there is NEVER a situation where you’ll be comfortable traveling with another family, there are also some pros to group vacations that may outweigh any cons:

• Date night is easy. Assuming that the other family is willing, you can trade evenings out with your spouse. You watch their kids while they watch yours. Enjoy big savings on sitting fees and feel safety in leaving your kids with a known supervisor.
• Shared experiences can build bonds. If your son and his cousin simultaneously chicken out when attempting Space Mountain for the first time, that’s a story they’ll laugh about later for years to come.
• There may be some economy-of-scale savings. This is particularly true if you decide to stay in off-site accommodations. Splitting the cost of an Orlando-area rental home may allow you substantially upgraded amenities for the same prices as staying on-site with a smaller party.

If you do decide to take the plunge, here are some guidelines you may want to set before you travel:

• Everyone pays for their own food. Tell your server at the beginning of each meal that you want separate checks. This eliminates hard feelings when the sirloin and martini eater wants to go halfsies on a meal with a teetotaler vegetarian, for the third time this week.
• Plan some time apart. Just because you’re vacationing together, that doesn’t mean you have to spend every waking minute together. If you plan to have some activities separately, that will give you more to talk about when you meet up again.
• Distribute tasks. Get everyone involved in the trip planning. This gives everyone ownership in making the vacation a success. This also ensures that no one person is overwhelmed with tasks like making dining reservations or planning itineraries.
• Write out a list of expectations. Items covered may include things such as expected bedtimes, souvenir budgets, or disciplinary tactics for typical misbehavior situations. Share the list with children. The more everyone understands what the common goals are, the fewer opportunities there will be for hurt feelings and misunderstandings.

Over the years, I personally have traveled to Walt Disney World with neighbors, my parents, my sister-in-law and her family, adult friends, unrelated young adult babysitters, and even a group of twelve teenage girls. There have been great successes (priceless photos of the extended clan) and some frustrating challenges. Meeting at 8:00 does actually mean meeting at 8:00, why don’t some people understand that? 🙂

What have your experiences been? Have you enjoyed your journeys to the World with others, or are you going nuclear-family-only from now on because of a negative situation? Give us your tips in the comments below.