Why You Should Travel With Your Parents As They Get Older — and How to Plan a Trip That Everyone Enjoys

Six tips for a trip that you'll all remember fondly, taking into account differences in interests, age, and ability.

When I was a kid, I took traveling with my parents for granted. Sure, they paid for everything, but they were also basically chaperones. To my brothers and me, they seemed hell bent on limiting our fun. For example, they took us to Denali National Park instead of Disney World; we sometimes stayed at hotels without pools (that’s your cue to gasp); and they never let us buy anything from the SkyMall catalog.

Of course, some 20 years later, I consider traveling with my parents, now both in their 60s, to be the utmost privilege. I know they’re no longer invincible, nor am I, and every day that passes brings us closer to our last. Fortunately, since graduating college, I’ve been able to cover some serious ground with each of them.

Together my dad and I have looked for the Loch Ness monster in Scotland, photographed wildlife in Grand Teton National Park, and most recently, survived the infamous Drake Passage while en route to Antarctica. Meanwhile, my mom and I have stayed at a $9/night treehouse hostel in Mexico, eaten at a Michelin-starred vegetarian restaurant in Vienna, and most recently, road-tripped through three states.

That’s not to say that all of our trips have been without hiccups, however. After all, even if you’re the apple that fell right under the tree, traveling with the people who raised you isn’t always easy. “There are always challenges as we are dealing with different physical abilities and interests,” says Alexis Sherry, a New Jersey-based travel agent. Still, Sherry is seeing an increasing number of clients requesting vacations for more than one generation. They can be difficult to plan, but so far she says she’s had no “disasters,” and often, her clients come back closer than ever.

“Our parents/caregivers are our earliest attachment bonds,” says Katie d’Autremont, a licensed professional counselor based in Bozeman, Montana. “It can be healing and fun to rekindle that bond in our adult years and as our adult selves.” She sees traveling together as the perfect opportunity for getting to know each other for who we are now, with “now” being the operative word. After all, as humans, we’re always evolving.

We’re also always busy. So, if you need a little help planning your next — or perhaps your first — trip with your parents as an adult, the following tips are for you.

Play '20 Questions' before you go.

“Start conversations early and be clear about expectations and possible boundaries,” says d’Autremont, who, coincidentally, is currently planning two trips with her husband and his parents. She believes communication is key and recommends asking questions: “What’s the goal of the vacation — leisure or exploration?” “Who is in charge of planning excursions?” “Will we do everything together or should we build in some solo time?” and perhaps most importantly, “Who will pay for what?” In her professional experience, Sherry says it’s always the parents who pay, but that could just be because she’s a travel agent. I know when my parents book travel for me, they pay up front. But when we’re on the actual trip, I try to chip in where I can. For example, my parents don’t have Uber (they refuse to download it), so I always take care of our transfers. I also love to treat them to gelato.

Take advantage of your 'adult' schedules.

“No more worrying about school holidays!” says Travel + Leisure A-List Advisor and luxury travel planner Jonathan Alder. Now that you’re grown, and your parents may be retired, vacations don’t have to revolve around a traditional calendar. Adler recommends traveling during quieter times when you don’t have to deal with crowds or surge pricing. For example, when my dad and I visited Jackson Hole, a popular resort town in Wyoming whose population balloons on the weekends, we were able to go mid-week because he was recently retired. It saved us hundreds of dollars and got us a room at a resort that’s normally sold out.

Try to travel with one parent at a time.

The dynamic is always different when I’m with just one of my parents. I find they listen better one-on-one, and they’re also more open to new things. For example, if I had traveled to Austria with my mom and my dad, my dad — a retired pork producer — would never have agreed to go to a vegetarian restaurant, and my mom would have joined him at a steakhouse in solidarity. Or, similarly, if my mom — who broke both legs in a car accident and still has issues with mobility — had joined my dad and I when we went to Argentina, we probably wouldn’t have spent our last free day hiking up a volcano.

Consider cruising.

When it comes to different generations traveling together, Adler is a big fan of cruising because there are always so many activities catering to a variety of ages and interests, and it’s easy to reunite for meals. I did a Danube river cruise with my mom a few years ago, and during the day I’d do the more active excursions like cycling and hiking while she visited churches and museums I had little interest in seeing. On the Antarctica cruise with my dad, I’d take painting classes or go to the spa on sea days while he attended lectures and read every book about Ernest Shackleton he could get his hands on in the ship’s library. We weren’t together 24/7, but the time we were together, we were energized and excited to share what we’d done in our “free time.”

Play TSA and inspect their bags.

My dad is notorious for packing things that either won’t get through TSA or are moot in this modern world. For example, he tried to pack a headset from the ‘90s on a recent flight to Buenos Aires. I had to tell him that airlines provide earbuds these days. And for the road trip I did with my mom, she brought a backpack filled with books on CD that she got at the local library. Not only did our rental car not have a CD player, but there was no way I was going to listen to a Nora Roberts marathon. I’ve also enjoyed introducing my parents to more travel-friendly clothing. Fabric technology has come a long way in the last few years, and while my dad still can’t pronounce Lululemon, he’s glad I introduced him to joggers. Otherwise he’d be sitting in economy wearing Wranglers so stiff they could stand up on their own.

Be patient and kind.

As our parents get older, they have a harder time getting around, and other health issues can obviously arise. When I travel with my dad, I have to keep in mind that he can’t be up and running first thing in the morning (which is when I’m always raring to go). He needs at least 30 minutes to change his insulin pump, and because he has diabetes, we have to stick to a strict schedule when it comes to eating. My mom, on the other hand, is experiencing some memory loss like her mother and her grandmother before her. Every time I’m tempted to get frustrated with my mom for forgetting to say “thank you” in the local language, I have to remind myself that she took care of me for 18 years — including my terrible twos. If your parents are anything like mine, they’ve made so many sacrifices on our behalf that the least we can do is be patient and kind.

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