Start With Why, Not Where

Most people start trip planning by asking:

Where should we go?

Experienced travelers start somewhere else.

They ask:

What do we want this trip to feel like?

Easy
celebratory
restorative
food-focused
romantic
outdoorsy
urban
slow

Once you know the why, the where becomes obvious. If you’re not sure where to begin, you could share your why with an advisor. Write down key themes or create an inspiration board. When something speaks to you whether it’s a vibe, restaurant you’d get on a plane for or bucket-list moment, it helps define what you’re seeking. And every trip is different, and serves you better in a certain time in the year or your life.

The biggest itinerary mistake I see isn’t choosing the wrong destination.

It’s choosing a destination before deciding what the trip is supposed to do for you.

The best trips are designed around intention, not geography.

Places can appear to scratch a certain itch, but in actuality, the trip becomes more exhausting than restorative, the goal of the trip wasn’t achieved or there was more effort than the reward.

Consider next time, what is motivating the trip right now?