We Don't Take Trips

When it comes to planning a trip, I stopped asking myself where I want to go a long time ago. Instead, I ask myself who I want to be with. Every departure from Maui, with thousands of miles of ocean between us and everyone we love, has to be justified by what is waiting for us on the other side. And what always justifies a trip for us is the possibility of quality time with family and friends. The long table. The reunions that only happen because we got on the plane. We don't take trips. We travel to connect.

Our trip to Barcelona wasn't about Spain. It was about reconnecting with friends we hadn't seen in too long and happening to be in the same city at the same time. We made the decision to make the detour from Italy without hesitation. Paris wasn't about Paris. It was about sitting across the table, twice over, on two separate trips, with two different families we love like our own. The city was the backdrop. The connection was the point.

I know how that sounds. Maybe limiting, like we are leaving entire parts of the world unexplored because we are too anchored to our people to wander freely. But I think the opposite is true. This clarity is not a limitation. It’s a compass. It means we never arrive somewhere without intention. We never wander anywhere wondering what we are doing there. We never come home feeling like something was missing. Because we build our trips around the pursuit of a feeling instead of a destination. And the love we get to experience with our people always delivers.

So this is the most practical travel advice I can offer. Because it immediately clarifies every decision. Ask yourself: Do I go? Who will I be with? What kind of memories do we want to make together? If the answers are good, you go. If they aren't, you wait for a better reason.

Start there. The destination will follow. It always does.

Where does your best travel begin — with a place or with a person? I'd love to know.