One-on-One Vacations with My Twin Sons

“What I love most about these trips is the bond that comes from being fully present with one child at a time.”

In this blog series we are walking through the four pillars of Resilience for Progress: Physical, Personal, Professional, and Prosperity. Each one shapes a fulfilling, resilient life. Today, I’m sharing how the Personal pillar comes to life in my own family through one-on-one trips with my teenage twin sons.

The idea started when I noticed how easily our conversations had shrunk into one-word exchanges. How was your day? “Good.” How was the event? “Fine.” Between school, activities, and friends, my high school aged sons are often on the move. I wanted a way to slow things down, to step outside the constant sense of busyness, and to connect with them as individuals. Taking trips with each son individually became a way to nurture the separate relationships.

With Avery, our first two annual trips centered on his love of all things theater. We have visited New York City twice, seeing Broadway and improv shows, touring the Broadway museum, and taking a walking tour of the theaters. On the first trip we stayed after Moulin Rouge for autographs, and he was giddy as the performers came out to greet the spectators. I will never forget him almost bouncing on his toes, turning to me with a grin, and saying, "thank you so much, Mom!" The highlight of our most recent trip was surprising him with backstage access to Harry Potter and the Cursed Child and The Great Gatsby. Enjoying theater productions has always been part of who I am, and sharing them with Avery created memories that belong only to us.

With Alex, the trips look completely different. Always reluctant to pick the next destination, two themes have resonated well for him: nature and adventure. In Las Vegas, he bravely jumped 829 feet from the top of the Stratosphere while I, too anxious to take the leap myself, cheered him on from below. Together we toured the Grand Canyon, taking in the beautiful landscape from the rim and climbing around the rocky terrain. The following year, in Rocky Mountain National Park, we hiked trails to stunning views and tackled the Via Ferrata, a guided climb along iron rungs and cables set into the rock face. I may not be a day-to-day nature lover, but stepping into his world gave me joy. These moments stretched me in ways I would never have chosen on my own, and that made them even more meaningful.

What I love most about these trips is the bond that comes from being fully present with one child at a time. The conversations flow more easily. Even something as simple as sharing a hotel room turns into a multi-day sleepover filled with shared stories and moments to savor. And sometimes the best memories come from the small choices, like when Alex wanted to order pizza in and watch a movie instead of going out to dinner. Saying yes made the night perfect for him without having to compromise planning with others.

These trips have taught me that relationships thrive when we make space for them. They have reminded me to let each child’s passions guide the experience. And they have shown me that traditions, even small ones, can carry forward. I hope my sons always let me take these one-on-one trips, even if someday the tradition extends to include their future families. What matters most is carving out intentional time and building memories that last.

For me, this practice is Personal Progress in action. Relationships do not flourish by accident. They require attention, planning, and care. Yet the return is immeasurable: deeper connection, stronger trust, and memories that sustain us through every season of life.

At the upcoming Resilience for Progress Retreat, we will explore how to apply the four pillars of Physical, Personal, Professional, and Prosperity to your own life. If this story sparks ideas about the relationships you want to nurture, I invite you to join us. Together we will practice intentional ways to strengthen the connections that matter most.