If you’re like me, you probably started bribing your parents and in-laws to go on family vacations even before you got pregnant. “Won’t it be great to create those memories with your grandchildren?” was my favorite line. While traveling with your parents guarantees built-in baby sitters, planning multi-generational family travel takes a lot more effort than you might think.

For instance, can your almost 70-year old father make it down into Antelope Canyon without complaining the whole time? Is your sister-in-law going to be as in awe of the Eiffel Tower as you were the first time she sees it or should you not make a big deal out of it?

What is it about multi-generational family travel that makes planning so difficult? Well, you know your partner and your kids and can plan the perfect vacation for your own little family, but what about when you start to add family members? You have to take different travel styles, personalities, and expectations into consideration. And the more people you travel with, the harder this can get sometimes.

But fear not 🙂 keep the below tips in mind while planning your next multi-generational family trip and you’re trip will be great.

Confirm your destination and itinerary

How annoyed would you be if you’d poured hours into your perfect itinerary only to find out that your aunt has zero desire to visit x-city? Forget annoyed, you might even be a little peeved, right? The very first thing you have to do if you’re planning a trip like this is to get everyone on board with the destination and places you plan to visit. When planning our trip to Arizona, I made sure that my parents were OK with not only the pace of our road trip but also the places I wanted to go.

This will also serve as your first lesson in compromise because with multi-generational family travel, you’ll learn, compromise is key. Plus your family should appreciate being a part of the planning process from the beginning.

Pro-tip: When planning your itinerary, don’t forget to take any kids’ or babies/toddlers’ schedules into consideration. Getting them on a good nap and eating schedule will be crucial to everyone’s enjoyment of the trip so don’t forget to consider the littles too!

Decide the length of the trip

I’m going to say something you won’t say out loud but I KNOW you’ve asked yourself: how long can I stand to be around these people?

If you’ve never gotten annoyed with another human being before, good for you. That’s a beautiful trait. I don’t know what that’s like. Being around anyone for an extended amount of time can test even the strongest relationship. So ask yourself how long could this trip be without ruining your relationship?

Think of the most annoying thing they could do and do the math on how many days in a row they could do that thing before you jump off a cliff. That’s the sweet spot. Congratulations, you’ve just decided the length of your multi-generational family trip!

Use a trip planning app like tripit.com

For organizational purposes, I highly recommend using a free trip planning app like TripIt. I used Travefy (while it was still free) to plan my family’s recent two-week trip to Switzerland and it was great. You can add all of your trip details and then share it with whoever you like. This way, you can keep yourself organized by the day as well as give people a heads up of what to expect and when.

If you’re like me, you love a good list or travel folder. For the sake of not having to depend on wifi/data, I keep it old school and still print hotel and airbnb confirmations, flight itineraries, and any attraction tickets I’ve bought in advance. But having the option to also have your whole itinerary conveniently on your phone is priceless.

Decide who’s going (and how many people)

Have you ever been invited somewhere and before answering if you were available, you ask who else is going? First of all, that’s rude.

But really, this is important. You want to enjoy your vacation so it’s probably not in your best interest to invite uncle so-and-so and his ex-wife, who both adore you but want to kill each other.

In my experience traveling with both my parents and my husband’s dad and sister this year, 4 adults is my limit. As the resident trip planner, I found myself anxious keeping track of luggage and people as we moved around Arizona and later Switzerland . I would not have been able to enjoy myself if I’d added more people (and more luggage). And luckily, there were no big fights because everyone got along (for the most part lol).

If you plan to have a larger party than just a few extra people than your immediate family, I’d recommend traveling to one place/resort or even a cruise. This would cut down on your coordination of tickets, hotels, etc.

Plan something for everyone

I would hate to go on a vacation and not get to do anything that I actually wanted to do. So it’s important to plan something for everyone in any age group or interest level. Maybe that means simply offering free time where nothing is planned so people can go shopping. Or it could mean planning an elaborate wine tasting and pairing with a Michelin starred chef for the food and wine experts in your group.

However you plan to include everyone’s interests, remember that some people will not be interested in some things while others will be thrilled about it. That’s OK; you can’t please everyone. But do your best to have something for everyone and you’ll feel good about the trip you’ve planned.

Anticipate questions from the less well-traveled

Did that make sense?

To save yourself a possible headache later, try and anticipate what questions or needs your less-traveled family members might have. For example, a packing list is always a great and gives people an idea of what they will and won’t need or shouldn’t forget. If you’ve got family who rarely travel by plane, be sure and remind them about ID requirements, weight restrictions on their luggage and what to expect when going through security. My husband is clutch when it comes to packing a carry-on backpack so he created a packing list just for what our family would want access to on the plane.

Don’t schedule TOO much

Remember earlier when I hinted at how much time you think you could spend with someone before you jumped off a cliff? Well, there’s a good chance that you overestimated just how much you could take and should probably schedule some “free” time where people can do what they want.

Vacations should be easy and planning every part of the day can definitely ruin the fun, relaxing part. I recommend planning at least a few half days where there is nothing pre-planned so that people can do whatever they want, even if what they want is still just to hang out all together 🙂

Plan the trip together

My last bit of advice is simple: plan as much of this trip together with those going. After all, it’s a family trip and planning it can be half the fun. To alleviate the pressure of planning everything yourself, you can delegate part of the planning to someone else. For example, ask your brother to find tickets to the sporting event he’s requested everyone go to. Or ask your cousin to help you find the best restaurants in the city you’ll be in and bring the list back to the group to decide where to make reservations. Planning together will also build excitement for the trip.

While this post was meant to make you giggle a bit, I do hope that it helped you decide how to go about planning your own multi-generational family trip. Traveling with family can test your relationship but it can also create memories that truly will last a lifetime and I can’t recommend it enough. If you can travel with your parents or adult siblings and your own children, please do. And let me know how the planning and execution went! I can’t wait to hear all about it.