What do the world’s most discerning travellers really want from their holidays? At Winged Boots, our travel experts spend their days crafting bespoke journeys for high-net-worth individuals who expect the very best (and then some).
We sat down with Winged Boots Personal Travel Manager, Jack Stean, to uncover the secrets behind luxury travel planning: from creating one-of-a-kind experiences to anticipating client needs before they’re even voiced.
Read on to discover what it truly takes to deliver travel at the very highest level.
Q: How important is hyper-personalisation to high-net-worth clients, and what does that look like in practice?
Jack: "Personalisation is absolutely in the top three things my clients care about. Five-star hotels and business-class flights are the foundation, not the finish. What makes the difference is the detail. That could mean arranging a particular vehicle for a day’s drive, complete with a mapped-out route, or ensuring a yacht is stocked with a client’s preferred fishing rod. These touches show that you’ve thought ahead and that you truly understand what matters to them."
Q: What role do privacy, security and discretion play in designing itineraries?
Jack: "Privacy and discretion are pivotal. Clients need to feel protected at all times. I exclusively work with trusted suppliers and deal directly with senior staff, often at general manager level, to maintain confidentiality. Sometimes we’ll use an alias for a guest until the final moment. The goal is to build itineraries where clients feel secure without sacrificing the extraordinary experiences they’ve come to expect."
Q: Which destinations or experiences are trending among affluent travellers right now?
Jack: "Japan has been hugely popular over the last couple of years. More recently, I’ve seen a rise in UK stays too – not just in London but in places like the Lake District and countryside retreats. Another big trend is revisiting destinations with older children, sharing favourite experiences from years ago or exploring further afield with a new perspective. Many clients want to return to the same hotel but pair it with something new, mixing the familiar with the unexpected."
Q: How do you define and deliver value when working with clients who can afford almost anything?
Jack: "Value is not just about price. Just because someone can afford it doesn’t mean they should overspend. Sometimes I’ll explain why a certain upgrade is worth it. Other times, I’ll be honest and say the second or third-best room in the hotel is actually the better fit for what they want. That honesty builds trust and ensures clients feel their money is working for them."
Q: How do you build trust with clients who are handing over their most precious resource – time?
Jack: "Trust is built over time but can be lost in seconds. Transparency is key. I’m upfront about things like resort fees, schedule changes or anything that might affect their trip. And when things go wrong, because sometimes they do, it’s about how quickly and effectively you respond. Clients remember how you handle problems more than how you celebrate the wins."
Q: What’s the most unusual request you’ve ever received?
Jack: "A client once flew into LA and wanted to attend Sneakercon in Las Vegas. He’s a big collector and needed a way to ship his purchases home rather than carry them. Finding tickets and transport was straightforward. The challenge was arranging for the sneakers to be collected, packed and shipped directly from the event. After a few calls to contacts in international logistics, we had it sorted. The shoes were waiting at his home within 24 hours of his return."
Q: With so much technology available, why do clients still prefer a dedicated travel expert?
Jack: "Booking a flight and hotel online is easy. But how do you know if it’s the right hotel for you? How do you secure the table at that impossible-to-book restaurant? What happens when your airline cancels at 2am?
"A travel expert knows you personally and takes all of that off your shoulders. Clients value the peace of mind that comes with having someone who understands their preferences and can handle everything seamlessly."
Q: In what ways do you go beyond logistics to act as an indispensible travel concierge?
Jack: "It could be calling or WhatsApping a client before they leave to make sure they’ve got everything, checking them in online, or even sending them a daily reminder of their itinerary. Sometimes it’s responding to unexpected events, like when there was a tsunami warning in Japan recently – I contacted clients to reassure them immediately. These things show you’re always one step ahead."
Q: Looking ahead, how do you see expectations evolving?
Jack: "Expectations will only rise. Hyper-personalisation will be more important than ever and the desire for unique, unforgettable experiences will keep growing. I can see a future where even the artwork and furniture in a room are tailored to a guest’s preferences. Clients will want to feel that every single detail has been designed just for them."
From tailoring once-in-a-lifetime experiences to offering discreet, round-the-clock support, Winged Boots travel experts operate at the intersection of luxury, trust, and personal connection. For our high-net-worth clients, travel isn’t just about where they go – it’s about how they feel at every stage of the journey. And that’s where our experts make all the difference. Because when every detail matters, only the best will do.
Our renowned concierge service is what gives us the edge, allowing us to provide seamless travel solutions for high-net-worth individuals.
See what our Head of Customer Experience, Claire Baker, had to say about her team's role in turning even the most outlandish travel dreams into a reality.
Read our interview with Claire
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