Going on a Multi-Generational Trip? Here Are 5 Rules to Keep Everybody Happy

These days, every airline has an app, an “add to iPhone wallet” feature and will undoubtedly send no less than 16 emails prior to your flight. But if you’re traveling with the over-50 set, it might be a good idea to print everyone’s boarding documents, copies of IDs and passports, itineraries, check-in confirmations, etc. ahead of time. For one, there’s the spottiness of Wi-Fi that comes with not only international travel but also domestic road trips. There’s also just the technologically unsavvy aspect of multiple generations (sorry, Aunt Irene). And that’s not an ageist statement: It’s difficult for even my millennial self to keep up with the newest way to pull up my seat number. Bottom line: Be prepared to be called old-fashioned with your file folder of papers—until the Paris train station WiFi isn’t working and you’re the only one with the tickets.

It can be tempting to migrate as a pack—safety in numbers, right? But I'm here to tell you that you don’t need to fly, drive or even stay together during multi-generational travel. For one, traveling separately means Gran and Pa can fly first class and drink wine in the airline lounge without feeling awkward for not including the rest. Plus, everyone’s schedules are different. The kids need a nap at noon? Hit the road at 6 a.m. so you arrive beforehand. And while it’s nice to have a helping hand with kid stuff—the travel stroller, car seat, pack-n-play—it’s also nice to change locations in smaller numbers. The same goes for accommodations. Wheelchair accessible and space for a crib? Finding Airbnbs or hotels that fit everyone’s demands will be difficult. Plan to make the most of the daytime activities instead.

Avoid awkward family money squabbles at all costs (so to speak). Before departing, make a game plan for how vacation expenses—meals, transportation, activities, accommodations—will be split amongst the group. Will Gran and Grampy cover dinners, plus one group activity? The cousins grocery shop and cook the group’s breakfasts? As a “happy anniversary,” are the adult kids going to split the big BBQ luau night evenly? Everyone picks up their own drink tabs? In France, my mom and her sisters each decided to pick up the tab for one dinner, which worked out well since there were five of them and five nights. Deciding these things ahead of time will make for less stress and better budgeting.

Speaking from the jetlagged experience of carting overweight and overstuffed luggage through the cobblestone streets of Paris at 6 a.m., do not make this mistake (or let other family members make it). Of course, parents of small children can hardly help that they have to schlep equipment wherever they go, but make it a point to be a carry-on-positive crew. Coordinate who’s bringing easily-shared items, like hair tools and power converters. Also, make sure a member of your group packs a foldable tripod for the coveted family photo when there’s no one around (or you haven’t learned enough French to ask a stranger politely).

While you may be tempted to keep the group entertained with a plethora of scheduled activities, avoid the temptation. Multi-generational family travel means taking into consideration everyone's differing ability to, say, hoof 18,000 steps through Paris. Build in plenty of downtime—for varying activity preferences, naps for all ages, family bonding, or just vacation magic. We stumbled upon the prettiest French bistro for my aunts and I to order Aperol Spritzes and cool off from the summer heat, which felt like a gift after taking in so many sights in the scorching sun. A good rule of thumb: Focus on one big group activity per day. That leaves time for—how do you say?—qué será, será.