What If You Knew It Was Your Last Trip?

We talk a lot about firsts in this business.

First steps in the sand.

First passport stamp.

First time on a plane.

First time seeing the Eiffel Tower or hugging Mickey Mouse or eating real-deal pasta in Italy.

But lately, I’ve been thinking about lasts. What if you knew this was the last time you’d see the ocean?

What if this was the last time your family would all sit at one table, all under one roof, all together in the same moment — no sports, no work calls, no distractions — just laughter, stories, and love?

That’s what this trip was for one of my Granny Group clients. Her last trip.  She knew it.  Her family knew it.  And they chose to go anyway — not in fear, but in celebration.

She told me during planning, “I want to take my family somewhere where we’ll laugh. Where I’ll be part of their stories — something we’ll talk about for years. This is what I want to talk about while I wait to die.”

(If that line doesn’t stop you in your tracks, I don’t know what will.)

She didn’t want a funeral slideshow.

She wanted memories that were alive and loud and messy and real.

And that’s exactly what we created.

It wasn’t about the hotel or the excursions (though they were great).

It was about the time. The togetherness.

The little hands in hers.

The joy of seeing three generations smiling in the same photo.

The quiet moments at sunset when she looked out and knew: this is the gift.

We spend a lot of our lives rushing toward the next milestone. But what if we paused and asked:

If this was my last trip, would I be proud of it? Would it feel like love? Would I be surrounded by the people who matter most?

Granny was.

And her family will never forget it.

If you’re reading this and wondering whether the trip is “worth it”… it is.

If you’re hesitating because the logistics are complicated or the timing isn’t perfect… do it anyway.

If you’re the grandparent thinking, Maybe one more trip with everyone — don’t wait.

Because sometimes the most sacred moments come not from the first time… but the last.

And when you know, and you do it anyway — with joy, with intention, with grace — it becomes more than a trip.

It becomes a legacy.