Most people start planning a trip by picking a destination. It seems logical. But I’ve found that destination is rarely the decision that actually determines how a trip feels. 

There are five decisions that shape every journey — and most travelers only think consciously about one of them. The other four happen by default. 

How much to move. One base or multiple stops? This choice alone defines whether a trip feels grounding or energetic. 

What anchors each day. Too many plans and the trip becomes a schedule. Too few and the day drifts. One thoughtful anchor per day, with the rest open, creates the best rhythm. 

What doesn’t make the cut. This is the hardest decision — and the one most people skip. But the trips that feel most satisfying are the ones where something was deliberately left out. 

Who carries the planning. Someone always carries the mental load. That weight shapes whether the weeks leading up feel exciting or exhausting. This is the decision that changes everything. 

Where to go. Yes, destination is last. But when the first four are clear, destination becomes much easier to evaluate. “Where should we go?” alone is almost impossible to answer. “Where should we go, given that we want five nights, a calm pace, and no more than one flight?” — that’s a question with an answer. 

Getting the Booking Order Right 

Once you understand these five decisions, the sequence of bookings matters enormously. Most people start with flights. But flights should come third. 

Start with your anchor property — the hotel that shapes how your days unfold. It dictates what’s walkable, what requires transportation, how the experience flows. The right property in the right location is more consequential than anything else you’ll book. 

Second, book the experiences with limited windows — the private tasting, the restaurant that seats twenty, the seasonal event. These become the stories you tell afterward. 

Only then book flights and transfers. By then, the logistics are straightforward. They’re connective tissue in service of decisions you’ve already made, not the other way around. 

Last, leave the in-between open. Day-to-day dining, spontaneous museum visits, neighborhood walks — these moments make travel feel alive. They work best when they’re not scheduled. 

Start With the Feeling

But here’s what should come before all of this: How do you want to feel when you walk back through your front door? 

Not where do you want to go. Not what do you want to see. How do you want to feel? 

Someone who says “restored” needs a very different trip than someone who says “inspired.” Someone chasing “reconnected” will benefit from a different structure than someone who wants to feel “adventurous.” 

These aren’t just words. They’re design principles. Once you know the feeling you’re after, every other decision becomes clearer. What kind of days produce that feeling? What rhythm supports those days? What destination naturally supports all of that? 

Most travel is designed forward: pick a place, research what to do, book accommodations, fill the days. Hope it works out. 

Backward design starts from the feeling and works toward the structure. It aligns the trip with what you actually need — not with where you think you should go. 

If you’re beginning to think about a trip and you’re not sure where to start, I’d love to have that conversation with you. Not the logistics — the intention behind it.