Multigenerational Travel: Celebrating Life’s Milestones Together

On the Atlantic Coast at Sam Lord’s Castle in Barbados.

If the pandemic taught us anything, it’s how precious time together truly is. For our family, that lesson hit hard when Ashley left for the University of Virginia in 2021. She began her college journey in the midst of uncertainty, and the family trips we had planned — a high school graduation trip to Italy and a junior year Spring Break adventure out west— were canceled. By the time she graduated in 2025, it had been since 2019 that we’d traveled together as just a family.

Her graduation became the perfect excuse to finally make it happen. Add in another milestone — my in-laws’ 60th wedding anniversary later that summer — and we had two beautiful reasons to celebrate. A multigenerational trip suddenly felt like not just a vacation, but a necessity.

Choosing the Right Destination

When traveling with three generations, the destination matters. We needed something easily accessible from both Philadelphia and Washington, D.C., with activities that would appeal to different interests and energy levels. A Caribbean all-inclusive checked all the boxes — and Barbados was the clear winner.

Located just a few degrees from the equator, Barbados in early June meant warm weather and less risk of hurricanes. Our resort was small and intimate, never crowded, with plenty of pool chairs, delicious meals, and live music each evening (where Nana proudly showed off her dance moves night after night).

The Gift of Uninterrupted Time

What struck me most wasn’t the scenery — as beautiful as it was — but the simple joy of watching generations connect. My daughters, now young adults at 22 and 19, interacted with their grandparents in ways that warmed my heart. They were patient, tender, and deeply present — qualities I might not have noticed in the busyness of everyday life.

One of my favorite memories was gathering in the gazebo after dinner, playing a question game that led Nana and PopPop to share stories of their youth, early marriage, and life experiences. I watched the bridge between generations narrow before my eyes.

At home, grandparents visit, but the girls are often pulled in a dozen directions — school, friends, jobs, activities. In Barbados, we had none of those distractions. Phones were down, schedules were clear, and we spent eight days immersed in nothing but family.

Why It Matters

As my daughters’ grandparents grow older, I am mindful that these opportunities are limited. Someday soon, my girls will begin careers and families of their own. These trips — these moments of laughter, connection, and storytelling — are treasures we won’t always have the chance to create.

Multigenerational travel is about more than the destination. It’s about honoring milestones, building memories, and reminding ourselves of what matters most: time together.

So take the trip. Celebrate the occasions. Play the games. Dance to the live music. Because we don’t know how many tomorrows we’ll have — but we do know that the memories we create will last a lifetime.

-Stacia