Disney World With Friends or Extended Family: Magical or Mistake?

Talk about Disney World long enough, and sooner or later a friend or relative will say, “We should totally go together, it would be awesome!” And maybe it will be! But most of us have that one friend (or maybe it’s your mother) that no matter how much you love them, you could never live with them. And it’s kind of the same with travel: just because you hang out three times a week doesn’t mean a joint vacation will be magical.

Group vacations can be fraught, but they have a lot going for them. When kids are along, date night is easy if you trade off babysitting duties. Shared experiences build bonds and priceless core memories that last for years. And you may find savings from economies of scale. So how do you know if your extended-family vacation to Disney World is a good idea or a bad idea?

Over the years, I’ve traveled to Disney World (and other places) with groups including my family, friends, and kids’ friends – with and without their own parents. Whether it’s your first visit or you’re the expert in the crew, here are some tips for making a group vacation to Disney World great. And that includes knowing when to consider canning the idea.

Don’t Take a Vacation From the Planning

On top of my own trips, I’ve heard gripes from some fair number of others who traveled with family or friends. A common thread? The “newbies go with experts” dynamic. The newbies let the experts take the lead on planning, but nobody talked enough about vacation styles or goals.

The good news: everyone doesn’t need to have the same vacation style to have a wonderful vacation experience. But you do need to plan with everyone’s preferences in mind. If you’re newbies, it might feel easy to sit back and let your expert in-laws do all the work. But once on the trip, voicing dissatisfaction is challenging. Either you’re afraid to mention it because you’re worried it will seem like criticism of the planner’s effort. Or worse, you do mention it and they get in a snit because they take it that way!

All-hands planning gives everyone a stake in making it a success. You don’t need a group vote on every tiny decision. But everyone needs to be comfortable being honest, respectful, and practical. That’s honest enough to say: “I don’t think we’d enjoy that.” Respectful enough to say: “OK, let’s find something else that works.” And practical enough to pick your battles; too many requests for compromise could leave everybody feeling that there’s nothing they’re excited about. Including you.

Here are some big choices you’ll need to navigate, and suggestions on making potential pitfalls work for everyone.

What’s Your Style?

There are people who like to make a plan. There are people who like to follow a plan. And there are people who like to not have a plan. If you’re happy to follow along in the wake of someone else’s plan, everything’s groovy. But if you don’t like to follow any plan at all, hitting the parks with someone devoted to a checklist ends with everyone grinding their teeth.

Obvious answer: You don’t need to be joined at the hip 24 hours a day. Committing only to a joint experience for one “must-do attraction” for each traveler is a common approach. You can, say, tour together with a plan for a few hours every morning before going separate ways. If one group is very into roller coasters, some alternate itinerary magic will ensure the ride chickens aren’t always cooling their heels and waiting. Or you might agree to pass on group touring and focus on group experiences like dinner and fireworks instead.

Pro tips: No matter what, everyone will enjoy some unplanned time that gives an opportunity to go their own direction. And if everyone prefers to be spontaneous, it’s still a good idea to have a method for choosing what to do. Spontaneity doesn’t mean no decisions are needed; it’s just making them on a different timeline.

Style is more than planning what to do

If you’ll be traveling with children, how do you handle discipline? Are you a vacation rule-breaker, or is bedtime still bedtime? Ice cream for breakfast for some and no dessert without vegetables for others is a recipe for tension. And for older kids, it’s not going to fly if one family is fine letting them roam the parks solo while the other set of parents wants full supervision.

Let’s say someone gets a bad cold. And they insist they’re not skipping the fancy sit-down dinner. Is someone going to spend the meal in a huff? You, as you picture them infecting the whole restaurant? Or maybe it’s you, as you stew in the perceived judgment over something you don’t think is a big deal.

Even things like Disney’s Lightning Lanes can be a source of friction. Some people are all in on paying a bit to minimize waits. Others are unwilling to buy into a “pay to play” model and view any form of line-skipping as the ultimate in rudeness.

These are the differences that may be irreconcilable. If your basic philosophy on these everyday situations is pretty far apart, it’s time to reconsider. In the long run, your relationship may be better off if you stick to socializing in small doses instead of traveling together.

Write it down for everyone

Make a record of everything you agree to while planning. Items covered may include things such as bedtimes, souvenir budgets, or disciplinary tactics for typical misbehavior. Don’t leave out expectations around promptness! Share the list with everyone, including kids. The clearer the general expectations are, the less likely you are to have hurt feelings and misunderstandings.

Also write down and share any firm plans that you make; tours, restaurant meals, and the like. You’ll find some tech tips to make that easier here: Sharing Disney World Plans With Your Group. And for in-park itineraries, you can share them in the TouringPlans Lines app. Don’t forget to include preferences collected during planning; they’ll help with decisions that you make on the fly.

Talk About the Money

Money is going to enter the conversation. Erin Foster, another TouringPlans group trip guru, notes that most folks in the US would rather sleep on hot coals than have an honest discussion about money. But despite the discomfort, you’ve got to have the money talk before embarking on a vacation with someone.

Are you a couple that needs space to unwind and decompress at night? Odds are, you’re doing nobody any favors by agreeing to share a Value resort room because your friends’ finances are a bit strapped. That’s especially true if, left to your own devices, you’d book a room at a 5-star hotel.

On the other side, if your finances don’t stretch to sit-down dining be honest about it from the get-go. You may not want to feel that you’re holding everyone back. But it’s up to them to decide whether a trip you can afford will make them feel that way. And spending your vacation feeling over-extended or guilty from budget anxiety won’t be a good time.

Perhaps you’re lucky enough to be going on a trip that someone else is paying for. You may still (you be the judge) want to confirm that holding the purse doesn’t mean they get to dictate all the plans. Because you might not be touching your bank account, but you’re still spending a precious resource – your vacation time. It’s fair to be clear that you consider that an investment too.

Where Will You Stay?

Money is obviously a question, but also – how much do you like everyone you’re traveling with? Get a large enough group together, and you’ll often find a “comes with”. That is, half the group can’t stand Uncle Joe for more than an hour or two, but he comes with Aunt Jane, who everyone adores.

If everyone, including the kids, is fast friends, then regular hotel rooms might get the job done. If not, think about digs with separate bedrooms and a shared living space. This allows you to replace some close-quarters activities like touring and dining with casual socializing that may minimize interpersonal frictions.

There are many such options off-site, and they can compare favorably in price to individual hotel rooms. If the budget will stretch to it, Disney Vacation Club Resorts have 1-, 2-, and 3-Bedroom Villas. The on-site option lets everyone use Disney transportation to come and go from a “home base”, even if some are sleeping in a cheaper room elsewhere.

What (And Where) Will You Eat?

Food is another area where vacation tastes and budgets tend to differ. My husband doesn’t consider it a vacation unless we eat a sit-down meal once a day. When my kids were little, I didn’t consider it a vacation if we did that more than once a day. Our budget couldn’t take it, and neither could my patience with the kids.

Add more people to the mix, and you’ll have more food preferences and differences in habitual mealtimes. If everyone isn’t on the same page, here are some suggestions:

• Plan for a DVC Villa or off-site condo-style accommodations with a kitchen; cooking (or DoorDashing) some of your own meals can accommodate both budgets and picky eaters.
• Everyone pays for their own meals in restaurants; avoid the friction when steak and cocktails wants to go halfsies with the teetotaler vegetarians … again.
• Commit to one meal a day, or a few special meals over the trip, to guarantee some together time.
• Splitting up to accommodate different tastes at Quick Service doesn’t mean that families need to stay together. Mix and match!

All Together Now

Disney World is a great place to take a vacation with friends or extended family. Partly, this is because it can accommodate so many different tastes. Rope drop to close commando touring? That works. Hanging out by the pool and ducking into the park for fireworks? That works too. But if you take a trip with others, then communication, planning, and flexibility will be the keys to making sure it doesn’t end in a meltdown.

Have you taken a group trip to Disney World? Would you do it again? Share your tips in the comments!