Three Questions I Always Ask My Clients That Change How They Travel

Every traveler brings a unique story, a personal rhythm, and a set of expectations to their trip. And as a travel advisor, my job isn’t just to book flights or find the world's best hotels, but to design experiences that truly resonate with who you are and what you want to take away from your journey.

To do that, I always start with three simple but powerful questions that help me (and my clients) see travel in a new light. Any of my clients can tell you that my consultations are thorough. I leave no stone unturned and ask questions they didn't even realize were relevant to their trip. These questions aren’t just about logistics, they’re about unlocking what travel means on a deeper level.

1. What’s the story you want to tell after this trip?

It might sound abstract, but this question shifts the entire planning process. Instead of asking “Where do you want to go?” or “What attractions do you want to see?”, I ask clients to imagine their post-trip story. Do they want to recount a tale of adventurous hikes through wild landscapes? Or maybe it’s about discovering quiet villages where time seems to stand still.

This storytelling mindset moves travel beyond ticking off destinations to creating a personal narrative. My clients take journeys that feel meaningful and memorable. It also helps uncover those less obvious experiences that will make a trip unforgettable.

2. What’s one thing you want less of on this trip?

Sometimes what we don’t want is as important as what we do want. For some clients, it’s less time in airports or fewer rushed mornings. For others, it’s avoiding tourist-heavy spots or overly curated photo ops.

Getting clear on this helps me tailor an itinerary that feels like freedom, not pressure. It also encourages clients to think about their energy and comfort. These two things matter deeply on any trip, no matter the destination or budget.

Most commonly, my clients ask me to help them find time to just wander. While I have built itineraries that are packed full of experiences, I almost always include blocked off time for spontaneity. And when my clients come home, the first things they're excited to share with me about their trips were what they accomplished during that spontaneity.

3. What’s your ideal pace?

This is where many travelers realize how different their preferences can be. Some want an adrenaline-fueled schedule, packed with activities from dawn until dusk. Others crave long, unstructured afternoons to wander, reflect, or simply relax.

Knowing the pace someone wants informs everything from how many excursions to book, to the type of accommodations that will support their downtime. It’s also key to avoiding burnout, so every moment feels like a gift, not a grind.

These three questions might seem simple, but they have the power to transform a trip from a generic vacation into a deeply personal experience. They help me meet clients where they are, understand their travel philosophy, and co-create itineraries that feel tailor-made... because they are.

If you’ve ever felt your trips missed something, or you left feeling like you just “saw the sights” but didn’t really connect, maybe it’s time to rethink the questions you ask before you book.

Travel is one of life’s richest experiences. The better the questions, the better the journey.