When you've already been everywhere everyone else is going..

There's a moment that happens to every discerning traveller.

You're at dinner with friends, and someone mentions their 'amazing' trip to that boutique hotel in Tuscany. The one with the Instagram-perfect infinity pool. The one that's now booked solid for the next 18 months because every influencer and their management team has discovered it.

You smile and nod, but inside you're thinking: 'I was there three years ago, before it became... this.'

This is the luxury travel paradox: the moment something becomes accessible to everyone who can afford it, it stops being what made it special in the first place.

Last month, I had a client tell me: 'Tess, I can book the Four Seasons anywhere. I can get reservations at the famous restaurants. What I can't get is access to the places that don't want to be found.'

That conversation led to a 20-day journey through the Cyclades that included zero Michelin-starred restaurants and zero five-star hotels - but did include an exclusive private tour by my good friend Giorgos —the same personal tour he gave to Obama and his family in 2024. A champion of sustainability, buying only from local farmers, he has inspiring stories to tell of his initiatives that most visitors never hear. You can't book this experience online. It only happens through relationships - a connection that took me 15 years to cultivate.

The difference? You can't Google your way to experiences like that. Money alone won't get you there. You need relationships, time, and someone who understands that true luxury isn't about thread count - it's about stories you'll never be able to tell anyone because they literally wouldn't believe you.

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My journey on the Venice Simplon-Orient-Express: Paris to Venice

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Why I Choose Every Place to Stay Like a Love Letter.