From Abergavenny to Guesture: The Story Behind Our Roots

Every journey has a beginning, and Guesture's story started not with boardrooms or business plans, but with the skies above Abergavenny.

This blog is the first chapter in the story of our rebrand — a journey that would eventually take us from AirFreedom to Guesture.

But before the rebrand, there was simply an idea:

a spark of inspiration drawn from freedom, travel, and the unexpected places life takes us.

The Inspiration: Paragliders Above Abergavenny

When I first moved to Abergavenny, I was captivated by the view of paragliders drifting gracefully above the Black Mountains.

Day after day, I would watch them from the ground, their bright sails dancing against the sky. There was something powerful in that image — a sense of freedom, aspiration, and vision.

It struck me that this was exactly how I wanted people to feel when travelling: unburdened, free to explore, with the world opening up in front of them.

That feeling became the seed of a name — AirFreedom.

A Detour in Crickhowell

Not long after, life took me to Crickhowell, where I managed the Manor Hotel.

It was a world in the Welsh hills, it gave me a grounding in hospitality that would shape everything that followed. I learned that running a property isn’t just about bricks and mortar — it’s about people, comfort, and creating spaces where guests feel at home, even when they’re far from it.

These experiences — the skies of Abergavenny and the hills of Crickhowell — slowly intertwined, creating the foundation for something new.

AirFreedom Begins in Newport

When I moved to Newport, the idea of AirFreedom became more than just a concept. What started as helping a few people in Newport with their Airbnb hosting quickly grew into something much larger.

I didn’t set out to build a business.

I simply wanted to help others give their guests the best experience possible. But word spread, and before long, AirFreedom had become a trusted name for property hosting and short-term rentals.

It was exciting, exhausting, and deeply personal.

The name carried all the meaning of its origins — the freedom of travel, the joy of hospitality, and the vision of creating something that mattered to people’s lives.

Guesture Story: The Beginning of a Bigger Journey

Looking back now, it feels almost inevitable that AirFreedom would evolve into something bigger. At the time, I couldn’t have imagined the twists and turns that lay ahead — or the rebrand that would later reshape our identity.

But that’s the beauty of beginnings: they rarely show you the full path, only the first step.

This is just the first chapter of our rebrand story — the birth of AirFreedom.

In the chapters to come, I’ll share how a sudden legal challenge threatened everything we’d built, and how with the help of Michael Tennant at Tennant IP, what seemed like a setback became the foundation for Guesture — a stronger, more resilient brand built for the future.

Follow our journey as we share more about how AirFreedom became Guesture.