Planning an international trip for six people is challenging; doing it with four teenagers requires extra preparation. When my twin sons graduated from high school in Australia, we celebrated with a three-week adventure across the US and Mexico.
Each son could bring a companion to make the trip even more special. Charlie chose his girlfriend, Jessie, while Thomas brought his best friend, Brad. As someone who’s explored 109 countries, I thought I had everything figured out — but traveling with teens quickly proved to be its own unique adventure.
A group chat became our planning hub, overcoming generational differences
I created a group chat for our six travelers eight months before departure. The chat served multiple purposes: It built excitement, answered questions, and helped my wife and me connect with our younger travel companions. This was especially valuable for Brad, who had never traveled internationally before.
While I informed parents about essential details, I intentionally let the teens handle most of the communication with their families. This approach gave them ownership of the adventure and built their confidence in traveling.
The challenge became finding the right balance. We quickly learned to save the group chat for crucial updates — too many messages from us “boomers” were ignored.
Letting teens help plan created unexpected choices
Rather than presenting a pre-planned itinerary, I created a PowerPoint showcasing different destination options. I admit this approach sounds incredibly dorky, but it increased their enthusiasm. Their choices surprised me — they chose to explore Joshua Tree National Park over visiting Disneyland and a week in wintery Chicago over warmer destinations.
This collaborative planning transformed what could have felt like a parent-imposed trip into a true group adventure. Everyone gave input, and then the group voted on where to go.
The group showed remarkable flexibility for each other’s interests
One of our biggest wins was how everyone embraced each other’s interests. Brad and Thomas love basketball, so we all watched a Chicago Bulls game. Jessie wanted to go ice skating, so we made time for a special session at Chicago’s Maggie Daley Park Ice Skating Ribbon. The whole group embraced my wife’s love for architecture with tours in Palm Springs and Chicago. No one complained about these individual activities; the group enthusiastically supported each other’s interests.
We expected frequent requests for “parent-free” time, but the teens joined almost every activity. They only slept in occasionally while my wife and I grabbed coffee or split up briefly, like when we explored Chicago’s Art Institute while they used their City Passes at other attractions.
We enjoyed alcoholic drinks together
Our time in Mexico created some of our most memorable moments. Since the legal drinking age is 18, we could share new experiences. We took turns choosing cocktails by the pool, tried different margarita flavors, and explored local bars. As parents, being included in these moments felt special, and we loved watching our kids and their friends transition into young adults.
These experiences were so enjoyable that we’re planning a reunion next month to recreate some of our favorite Mexican cocktails and relive those memories.
Capturing memories became an essential part of the trip
Each evening, we gathered to share our daily highlights, which I wrote in my Notes app. This simple ritual became part of our routine, and on the last night, I compiled these moments into a summary for everyone. We also maintained a shared photo album that started with just my uploads but soon filled with everyone’s snaps. It felt like the age difference became less noticeable as the trip progressed.
The trip worked because we found a balance between structure and freedom. The teens felt involved but not overwhelmed. Throughout the trip, they had privacy when needed but joined most activities.
Perhaps the most unexpected measure of success was that Brad and Jessie accepted my Instagram friend request, an unexpected victory in the world of teen social media.
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