Travel planning for families especially when you’re wrangling teens and tweens often feels like mission control. You’re juggling budgets, schedules, and, most importantly, expectations. We all want the same thing, to bring home not just souvenirs, but truly great, shared memories for everyone. But here’s the secret I learned the hard way, if you assume you know what will make everyone happy, you risk missing the best connections of all. From realizing a centuries-old ocean liner could appeal to a teenager, to trading in a standard activity for an evening of inventing "Chesskers" in our matching pajamas. I discovered that the most valuable part of any vacation is setting aside your own agenda to make sure every single traveller feels seen, heard, and completely included in the adventure.
The Trap of Assuming I Knew Best
As the family planner, I often fall into the trap of thinking I know what will work for everyone. We recently had a trip that proved just how dangerous that assumption can be.
On our most recent trip to LA to visit Disneyland. I nearly missed out on a deeply personal experience simply because I figured no one else would be interested, a tour of The Queen Mary. My great-grandfather was a sailor on that ship, and I was genuinely ready to skip it, resigned to the disappointment that the historical aspect would be a guaranteed snooze-fest for the rest of the family.
It was a casual mention, a thought I voiced aloud that changed everything. The moment my girls mentioned that The Queen Mary is known as one of the top 10 most haunted places in the world and that they would love to go, I had to set out to restructure our trip. My quiet historical interest transformed instantly into their must-do teen adventure. We didn't just tour the history, we did the ghost tour, and the unexpected thrill of it became one of our collective highlights. My lesson was clear, Don't assume, just ask. As parents, we often act as the 'travel advisor' for our families. I realized as I moved forward in this new career as your Travel Advisor I would love to include the whole family in the planning.
Meeting Them in Their Galaxy
Strong family bonds aren't just built hiking up mountains or visiting museums, they are built wherever you truly connect. And sometimes, that place is the resort's common area.
While visiting Dreams Royal Beach in Punta Cana, we carved out time to simply hang out in the resort's teen area one evening (which may be allowed if yours are the only teens there, or during open house hours). We joined the girls in these cool gaming pods for a how to session playing video games. I had the realization that slowing down and just enjoying each other's company is so important. It’s easy to feel a little awkward stepping into a world where your kids are the experts, but you have to remind yourself we constantly ask our children to face new experiences. Why not step out of your own comfort zone to meet them in theirs? A little discomfort is absolutely worth the chance to connect.
This spirit of adaptation led to one of our most unique memories. The resort had a giant outdoor chess game, but not all of us knew how to play. So, late one night, the girls invented Chesskers, a combination of chess and checkers. It became a nightly event once we were all in our matching jammies. The connection you make during that time, when you ditch the rulebook and create your own fun, will help your relationship stay strong well after the trip.
We saw the same connection in action at Disneyland when we added a special Droid building session for Dad. He was talking about it so much we finally had to force him to go. Although we are not huge Star Wars fans, it was so much fun. I enjoyed watching my husband and teenage daughters pick out all the parts together, and it was easy to get lost in the immersiveness of Galaxy’s Edge. The quiet joy of watching them collaborate and create was a rewarding experience, plus Dad got to bring home an awesome souvenir.
The Planner’s Secret: Everyone Gets a Win
To ensure no one felt overlooked, I relied on a simple strategy for our Disneyland trip, everyone submitted a wish list of their top three rides or experiences. It was easy to come up with a list after watching so many youtube videos in preparation.
I made sure to have a game plan based on what activities to 'rope drop' and which could be left for later in the day. I was focused on ensuring the things we were most excited for were done early in the trip, just in case there was a chance to do them a second time. This approach built excitement and trust.
When we were able to pivot like securing an extra Individual Lightning Lane for us to ride Radiator Springs Racers again at night (I would 100% suggest you budget for this) it instantly elevated the entire trip. But sometimes, the best "pivot" is forced upon you. On our very last night, we got stuck on Big Thunder Mountain, which initially felt like a huge waste of valuable time. The moment we realized we were going to be evacuated off the ride, however, the mood shifted completely. That unplanned experience became a huge bonus, we got a free Lightning Lane pass, saw things few guests ever get the privilege to see, and snagged some truly unique photos. It proved that even when things go wrong, embracing the moment can turn a frustration into an exclusive, unforgettable memory.
It's also important to remember that not every shared experience will be a hit. Take Guardians of the Galaxy: Mission Breakout. Let's just say that was a one-and-done for most of us! Yet, those moments of shared suffering and laughter created a powerful bond. We still reference that feeling of being completely terrified together. Sometimes, the fails become the richest memories.
We also learned boundaries. While my youngest daughter and I loved leaning over the side of the boat to join a dolphin stampede during a Newport Coastal whale watching tour, my oldest, who had the courage to join us on the boat, realized as we lost sight of land this activity wasn't for her. Then the sea sickness kicked in, she and Dad decided next time they will stay on shore. I was grateful for her courage because without it I likely wouldn’t have booked the trip and seeing whales would have still been on my bucket list. It was still a great experience that we learned from.
The Unexpected Detour: Local Gems and Shared Chaos
One of my favorite, most enduring memories came from throwing the original plan out the window. We were in Punta Cana and wanted an animal excursion, naturally thinking of the typical dolphin or monkey tours.
A gentleman at the resort desk suggested something different, Eco Park, a place he noted that local families also visit. We loved the idea of a less-touristy option, and it was perfect. We got to feed lots of different animals including baby pigs, take a scenic bamboo raft ride, enjoy the thrilling swing over the hill, visit their dog shelter, and even brought home some honey from their beehives. The open-air hop-on-hop-off bus tour around the park was almost as thrilling as the swing!
Then came the grand finale, horseback riding through the valley. All was going well and we were pushing through the nervousness. Then we ended up getting caught in a torrential downpour. We were soaked, laughing hysterically, and fully immersed in an experience none of us had planned. It proved to us that the true reward of travel isn't ticking off items on a checklist, it's the beautiful, spontaneous connections you forge when you listen to your family, let go of assumptions, and embrace the chaos together.
The Power of Tradition: Mom and the Girls
While full-family chaos creates robust memories, focused one-on-one (or one-on-two) time is equally vital for connection. For us, that means our annual trip to the Stratford Festival.
This tradition is my essential break from the usual mom routine of running the household. It’s dedicated time spent with just the girls, pursuing an interest Dad would happily sleep through. We get dressed up, eat good food, shop the quaint stores, enjoy the quiet rhythm of the cafes and gardens, and immerse ourselves in one or two of the world-renowned plays. This quieter tradition allows for a different, more mature level of connection and conversation. It’s a dedicated time when I can see them as young adults with maturing tastes, and it’s a connection I deeply cherish and hope continues long into the future.
Bringing It All Home: A Call for Connection
The truth is, your kids won't remember every famous landmark you painstakingly planned to visit. They will remember the feeling of fear and fun during a ghost tour, the shared adrenaline rush after a terrifying ride, the collaborative chaos of inventing a new game, and the pure, unscripted joy of getting soaked together in a tropical storm, the road trip for a couple of nights away from the ordinary.
Connecting on a family trip isn't about perfectly executing an itinerary, it's about being flexible enough to let every person bring home a good memory, even if that memory means staying on dry land or losing badly at a video game. It's about recognizing that sometimes, the best part of being a parent is allowing your child to guide the adventure, or just enjoying the quiet ritual of a beloved annual tradition.
Travel Tips for Traveling with Teens:
- Implement the "Top Wishes" Rule: Before you leave, have every traveler including the parents list a couple of their would love to do activities. This ensures everyone feels invested and guarantees a minimum level of satisfaction for all.
- Embrace the "Pivot": If you hear a local recommendation or your child expresses a spontaneous interest (like Droid building), be willing to spend the time to shift the schedule. The unplanned activities often yield the deepest connection.
- Dare to Be Uncomfortable: Dedicate time to activities your teens love, even if you are totally inexperienced (like gaming). Showing up in their world validates their interests and creates powerful bridges of communication that last long after the vacation ends.
Need a Travel Advisor to Uncover Your Family's Ghost Tours and 'Chesskers'?
Planning a trip where everyone feels seen can be a challenge, but it’s always worth it. If you need help structuring a wishlist strategy, finding local gems, or just brainstorming ideas to get your teens talking, I'm here to help you start crafting those unforgettable experiences that turn into lasting memories.
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