Traveling with Parents? Here’s How to Make It A Great Trip
Traveling with loved ones as an adult can be both rewarding and stressful. Sharing new experiences is wonderful, but extended time together in a new environment can test even the closest relationships. Honest conversations early on help ensure everyone is on the same page. More than the trip itself, what matters is making time together positive and stress-free—especially when the unexpected happens (and it will!).
Couldn’t help but play a little joke on my parents as I welcomed them to Asia at Singapore’s Changi Airport! Full credit to my brother-in-law for the funny idea!
I’m truly lucky to have parents adventurous enough to visit me in Asia from Canada—and who have supported my travel dreams since I was little and they saw how much exploring meant to me.
“When I invited my parents to visit me on a five-week, five-country trip in Southeast Asia, I quickly realized that although we share a lot of love, we also have very different rhythms.”
After years of living independently, I had to adjust my expectations to balance family time and personal space. With open communication and planning, we made the most of our trip—though there were bumps along the way. I still wish I’d been more patient, but we all cherish those five weeks and the privilege of sharing that experience.
Being silly on Hanoi’s famous train street (far between the train’s scheduled visits!) - we came back later since we missed it passing through, and it was well worth the experience!
1. Key Questions to Ask Before Booking
Make Sure You’re on the Same Page
In my case, my parents weren’t too interested in participating in the trip planning and were happy for me to plan it. But there were still some important questions we needed to discuss to make sure I planned something that would be interesting and fun for everyone. Before booking flights, we discussed the following to make sure we were on the same page:
Where do we want to go? Do we want to stay in one place or move around?
What’s the budget, and who is paying for what?
What types of accommodations do we prefer?
How can we make spending so much time together most enjoyable and relaxed?
How much do we want to plan versus being spontaneous?
In my case, since I was working remotely for part of the trip, we also needed to discuss how to balance my work with travel and spending time together.
This discussion was the foundation for our planning going forward. After we discussed this, I presented them with a general itinerary (destinations, main events and activities), and we had fun dreaming up this holiday from there.
I rough it a lot more often when I travel solo, but with my parents, we treated ourselves to pretty nice hotels or Airbnbs throughout this trip. This was a fun night relaxing at Metta Residence & Spa in Siem Reap, Cambodia, after a long day of sightseeing the city’s ancient temples.
2. Use a Shared Planning Tool
TripIt or a Shared Calendar = Your Best Friend
To keep everyone on the same page, I put all of our travel plans into my TripIt app, which my parents had access to. This way, they could easily check booking details and the itinerary whenever they wanted. This also helped to reduce their reliability on me at times.
TripIt has its limitations, but it’s still a great tool. You can setup auto-forward for booking confirmation emails, and it will organize your hotel reservations flight tickets and more into your itinerary. I also manually added notes, like which days we’d be in each city and visa reminders, to make it clear for everyone.
If TripIt isn’t your style, you could do something similar using Google Calendar or Apple Calendar, but I love that TripIt has both an app and desktop version, plus the email integration and flight check-in reminders. It will simplify your life.
Cruising down the Mekong Delta on one of the last days of our trip — this was a relaxing way to end the trip since we booked with GetYourGuide, so the planning was minimal.
3. Share Responsibility for Planning
Appoint a Planner but Share Decisions
Now that you have the tools, it’s time to think about who is responsible for organizing different parts of the trip. While I’m naturally the planner, I made sure to involve my parents in decision-making. I narrowed down options for flights, accommodations, and activities, and we discussed them together. This helped them feel included and gave me some relief from handling decisions alone.
“There’s usually a “planner” personality in the group, but sharing decisions makes everyone feel more engaged and reduces stress on one person.”
Since my parents’ trip to Southeast Asia was a long one, we only planned accommodations, flights and trains for the first 3 weeks in advance. We wanted to see how things were going, what they liked and what they didn’t like, and then plan the rest together.
It can be a lot of pressure on one person to organize a trip that will please everyone. Even if I don’t feel my parents would hold it against me when something goes wrong, I really wanted to create an amazing experience for them and would feel bad if I accidentally sent them to a dumpster of a hotel. They understood this and we agreed to share responsibility for planning and to roll with the punches.
4. Roll With the Punches
Stay Calm & Remember: The Best Memories Are Often Unplanned
From missed flights to hotel rooms that don't meet expectations, there will inevitably be moments where things go off course. Instead of trying to control everything, it’s best to adopt a flexible mindset and embrace the opportunity for spontaneity. Sometimes a missed train or a rainy day can turn into a cherished memory.
Allow for some downtime and unplanned adventures—it’s often in those moments that you find the best parts of your trip.
Don’t Let a Change in Plans Become a Catastrophe
Things will go wrong sometimes. So instead of catastrophizing it, look for the opportunities in it. A missed flight could mean more time somewhere cool, or another opportunity to eat that amazing curry you discovered, or simply more time to rest instead of burning out with go-go-go travel.
For example, we ended up having an issue with our visas to enter Vietnam — which meant we were denied boarding our flight out of Siem Reap, Cambodia, with no idea when our visas would get approved. Yikes! We ended up taking a night bus down to Kampot, in the south of Cambodia. We spent time there in nature for a couple of days until our visas were approved, and it turned out to be such a lovely unexpected side adventure.
During that instance at the airport counter, I needed some space to discuss with the airline and make some calls, so they went to find us some food while I sorted things out. I was really glad that they didn’t panic and trusted me to handle it, because it would have been more stressful otherwise.
“At the end of the day, most of my best travel memories stem from unplanned — and even seemingly catastrophic events at the time turn into the best opportunities. Stay open to the possibility!”
The biggest challenge we faced logistically was that our Vietnam visas were delayed. We decided to hop on an overnight bus to Kampot, in the south of Cambodia, and had a great time in nature there until our visas came through and we were able to head to Hanoi. The overnight bus was a bit rough, but a memorable adventure! I’m so impressed that they agreed to try it :D
5. Respect Different Rhythms & Needs
Consider Everyone’s Interests
Give everyone space to explore what excites them, even if it’s not your thing. While I love historical sites, my dad prefers live music, and my mom enjoys craft workshops. In our downtime, we had different preferences too—walking, swimming, or in my case, blogging. Some activities we did together; others, separately. Building in guilt-free time for individual interests keeps everyone happy and engaged.
Even on a family trip, you don’t need to be together 24/7. Whether it’s exercise, blogging, or a quiet walk, personal recharge time is essential. This not only maintains mental well-being but also makes shared experiences more enjoyable. A little flexibility goes a long way in keeping the group comfortable and energized.
Create Conditions for Personal Space
After years of living alone, I had to adjust to my parents’ different expectations of personal space. I prefer quiet mornings, while they were ready to chat and plan the day. It took some adapting! To enjoy your time together, everyone needs both physical and mental space.
“No one should sacrifice what keeps them happy—whether it’s enough sleep, a workout, or time alone. If you want to relax on the beach while others go shopping, go for it! Compromise is valuable, but honoring your own needs ensures you’re better company later.”
To maintain physical space, don’t cram into one hotel room. While we shared for two nights in Singapore to save costs, we mostly booked separate rooms or large Airbnbs with private spaces. The Airbnbs ensured that my parents also had more space than when they shared hotel rooms, which can be quite small in Asia! We found big Airbnb apartments that were very affordable in both Bangkok and Saigon.
My parents initially struggled with the idea of doing things separately, but after I sent them on a date night in Kuala Lumpur while I caught up with a friend, they saw the benefits. The odd opportunity like this gave us all space to come back to each other fresh and excited. Alone time prevents burnout, and when you reunite, you’ll be more relaxed, refreshed, and have more to share. Giving each other breathing room also helps avoid irritation or resentment, making the trip more enjoyable for everyone.
Some nights were very social - like that time I took my parents out on Khao San Road (yes…Bangkok’s Red Light District — they have surprisingly great live music!). Other evenings were for alone time and recharging.
6. Set-up Local SIMs and Apps
Ensure Communication and Self-Reliance with Local SIM Cards
One of the first things I did when my parents arrived was set them up with local SIM cards so they could stay connected without relying on Wi-Fi or my hotspot. This made a huge difference because they didn’t need to rely on me to look things up, check schedules, book a car, etc. This was also critical, of course, to make sure we could easily text or call each other when needed.
In Southeast Asia, you can find SIM cards or eSIMs that provide coverage across the region, so you don’t even need to change it each time you cross a border.
Set-up Vital Travel Apps
If your travel companions aren’t tech-savvy, take a little time at the start of the trip to set up and explain essential apps like Google Maps, WhatsApp (not common in Canada and the USA, but vital for travel almost everywhere else), and airline apps for mobile boarding passes. It’ll save you any last-minute frustration later.
My parents are adventurous and happy to try new foods that I suggest! They had fun at night markets all around the region.
Some of the apps I most recommend are:
TripIt for travel planning
Whatsapp for international messaging and communicating with local businesses (ex. restaurant reservations, hotel pickup arrangements, etc.)InDrive
Grab, InDrive and/or Uber (country-dependent) for rideshares
Google Translate for communicating with locals
Google Maps for walking directions
xe for currency conversion rates
GetYourGuide for booking activities and tickets
Relevant airline apps for quick check-in and mobile boarding passes
Booking.com for researching and booking hotels
To my surprise, my parents enjoyed tuktuk rides! Here we were in rural Cambodia enjoy the quiet countryside atmosphere.
7. Let Go of Old Dynamics
Spending extended time with family as adults is a trip—literally and figuratively. Old dynamics resurface (hello, teenage eye rolls), but letting the little things go makes for a much better time.
One thing I always try to remember is that everyone experiences the world differently, and their reality is just as real as yours.
“What excites or shocks one person might not even register for another, but that doesn’t make it any less valid. My parents were blown away by things I wouldn’t have given a second glance, but instead of brushing it off, I tried to see the trip through their eyes. Their excitement made me appreciate things in a whole new way.”
At the end of the day, travel is about making memories together. That means rolling with cultural misunderstandings, unexpected connections, and weird but wonderful experiences that push us outside our comfort zones. And honestly? Those are usually the best stories anyway.
My parents always make friends everywhere we go - it’s one of their best qualities! While waiting for our ferry to Phuket from Klong Jirad Pier in Thailand, we had fun chatting with this lovely family from India.
8. Check Yourself
Mom and dad are also living life for their first time. None of us have it all figured out.
When we put in effort to grow and to understand people we care about, we show up better for them and build stronger relationships. Acknowledging where you can improve—and having open conversations with your parents or travel companions about strengths and weaknesses—helps you travel together more smoothly.
For instance, I’m the planner, so I took care of the trip details like booking accommodations and flights. But my mom’s sociability was just as crucial—she helped us connect with locals and made sure we didn’t miss out on those spontaneous, personal experiences that made the trip memorable. And my dad’s better sense of time meant we were reminded when we had to go.
At the end of the day, traveling together isn’t just about seeing new places—it’s about sharing and bonding over a special experience together. The more you embrace that, the more meaningful (and fun) the experience becomes. And yes, that is often easier said than done, but it’s always worth trying.
Exploring under the sea during a day trip from our secluded hotel in Krabi, Thailand.
Enjoy Your Travels!
Traveling with parents or other loved ones can be a deeply fulfilling experience, but it requires more than just a well-planned itinerary. It’s about balancing the group dynamic, creating space for individual needs, and understanding that things won’t always go according to plan—and that’s okay! With the right mindset and some planning, you can ensure that everyone feels valued and respected, and that everyone has the opportunity to create their own memorable experiences along the way.
Eating banh mi — in my opinion, the best sandwich in the world — on the streets of Saigon, Vietnam, with our awesome local guides for a day in the city.
While it can be challenging at times, the effort you put into planning and maintaining open communication will ultimately make your trip more rewarding. Be patient with yourself, your family, and the unexpected moments that arise. You’ll be talking about this trip for years to come — laughing about the unexpected twists, the funny reactions you each had, and the people you met.
So, whether you're embarking on a weekend getaway or a month-long adventure, take the time to plan thoughtfully, communicate openly, and, most importantly, enjoy the journey together!
Time to go home! After 5 crazy weeks of travel through 5 countries, they were looking forward to going home at this point. But it’s always hard to saw goodbye.
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