Stop Asking Where to Go. Start Asking Why.

Most people start travel planning by asking a familiar question: Where should we go?

It’s understandable—but it’s often the wrong place to start.

Some of the most memorable trips aren’t built around a destination at all. They’re built around an interest. A passion, a curiosity, a long-held fascination, or even a single thread that ties the journey together. The places matter, but they’re not the point. They’re the setting.

I’ve seen this firsthand. One of my favorite trips in recent years grew out of following the Washington Capitals through Western Canada in January 2025. Hockey was the organizing principle, not the entire experience. The route created opportunities—cities, side trips, meals, landscapes—but the interest gave the trip coherence. It shaped the rhythm, the choices, and the memories.

That’s the power of interest-led travel.

In intelligence analysis, arguably the most important key to success is taking the time up front to ensure you are answering the best question. We call it the Key Intelligence Question, or KIQ. The same concept applies to travel.

When a trip is designed around an interest, it immediately answers questions travelers often struggle with. How long should we stay? What’s worth prioritizing? Why this city and not the next one? Instead of trying to “see everything,” the itinerary filters decisions through a single lens. The result is usually less rushed, more intentional, and more personal.

Interests don’t have to be narrow or obsessive. In fact, they work best when they’re broad enough to allow variety. Sports, food, history, architecture, literature, nature, genealogy, music, film, faith, craft, learning, or even a particular era of history can all serve as anchors. The trip still includes iconic sights and spontaneous discoveries, but everything feels connected rather than random.

This approach also changes how travelers experience familiar places. A city stops being a checklist and starts becoming a classroom, a stage, or a backdrop. A mountain town becomes more than scenery when it’s tied to outdoor tradition or environmental history. A market visit feels different when food is the through-line instead of a filler activity. Even downtime feels earned rather than wasted, because it supports the larger purpose of the trip.

Interest-based travel is especially effective for repeat travelers. If you’ve “done Europe” or “been to the Caribbean,” the question isn’t where to go next—it’s why. Framing a journey around an interest allows travelers to revisit regions in new ways, often discovering places they would have skipped entirely if geography were the only guide.

It also lends itself well to deeper planning and better value. When the purpose is clear, it becomes easier to decide where to splurge, where to simplify, and where independent exploration beats a packaged experience. The trip feels designed, not assembled.

This philosophy is shaping how we think about future offerings as well. Beginning in 2027, we plan to introduce espionage-history–themed travel—journeys built around intelligence history, Cold War sites, and the stories behind them. These won’t be novelty tours or surface-level sightseeing. They’ll be interest-driven itineraries that use place as context, not the headline.