Meet Josiah (Jo for short) – UK cycling guide whose love of cycling was sparked far from home and fuelled by a taste for big adventures. Having seen first-hand how travelling by bike opens the world and the people in it, he jumped at the chance to join the Skedaddle guiding team! We caught up with Jo for a Q&A to learn more about his story…
Tell us a little bit about yourself…
When I first left Kent to study at University in Wales, I had no idea I was about to stumble across the wonderful world of adventure and outdoor sports. It still amazes me I managed to squeeze law lecture and essays between all the cycling, hiking, kayaking and climbing I discovered there.
After graduating, I set off on a ‘gap year’ to ride my bike from England to Australia. Well, three gap years later and I finally rolled into Sydney with 40,000 kilometres of stunning vistas, interesting people and memorable riding – across deserts, jungles, and mountains stretching behind me.
Since then, I’ve loved guiding people on their own adventures, helping to showcase the beauty of our world from the saddle, and encouraging them to overcome the challenges encountered on these sorts of trips so they too can learn about themselves and enjoy the taste of achievement.
What got you passionate about cycling?
Setting off to cycle around the world, I never really believed I’d make it. But, on those early days, I remember watching my progress inch across the map in disbelief at the distances you can cover on a bike – and finally daring to believe this audacious dream might really be possible. That sense of wonder about how far you can travel on a bike has never left me.
This passion only deepened as I discovered how a bike breaks down barriers between people. Daily, I was stopped by people from all walks of life who wanted to know where I was going; they invited me to share a meal or perhaps sleep a night in their house. These interactions were among my favourites.

What’s your history with Skedaddle?
I’ve seen first-hand how travelling by bike changes the way you see yourself and the world around you and it’s a privilege that my job as a Skedaddle cycling guide lets me take other people on some of the most beautiful riding the UK has to offer. When I first discovered the job opportunity during COVID, it took a fraction of a second to decide to apply!
My first trip for Skedaddle was Cotswolds – Bourton-on-the-Water based out of the grand HF house there. The weather was great, the group was lively (in the best way!), and we enjoyed three superb days riding around the Cotswolds. I almost couldn’t believe I got paid at the end!
What is your favourite trip?
For the pure joy of riding my bike, the Caledonia Way is an absolute favourite for the spectacular riding every day and the varied scenery you witness as you traverse a less-visited slice of Scotland from coast-to-coast.
I also love the Lands’ End to John o’ Groats trip. There’s a misconception that the UK is crowded and you need to travel abroad to find true outdoor adventure; A LEJOG trip certainly dispels that myth as you travel for three weeks across the country watching the landscapes of Cornwall blend into the wilds of Scotland with endless great and undiscovered riding in between. A similar transformation happens to each cyclist as the pre-trip nerves at Lands’ End melt into the euphoric sense of achievement at John o’ Groats.


What’s your favourite Skedaddle memory?
I find that at the end of every tour or season; my favourite memories always revolve around the friendships I’ve made while on tour – both with the group of cyclists and the team of other guides. When every day revolves around pedal strokes, exploring a new area, and enjoying great food, friendships form quickly and deeply. On a recent Lands’ End to John o’ Groats, most evenings my stomach hurt more than my legs because of so much laughter.


What’s your favourite power snack and why?
Towards the end of a long, cold day in Scotland, when the 10 kilometres to the guesthouse seemed an impossible distance, my fellow guide, Lorna, produced some buttered malt loaf. The salty butter complemented the rich sweetness of the spongy cake, and she struggled to make more as fast as we could eat them. Suffice to say, it was rocket fuel to reach the guesthouse, and more malt loaf shot to the top of the shopping list when we reached Fort William.
What’s your top packing essentials for a cycling holiday?
The line between an enjoyable trip and a miserable one can all come down to being uncomfortable. Bring clothes and equipment you’ve worn and used before, so you’re not ‘breaking them in’ for the first time on your holiday. On that note of comfort, if you’re renting a bike, take the time with your cycling guide on the first day to dial in your bike fit!
Tell us something about you we might not know…
I spent much of the Covid lockdown stuck on a tiny island in the Arctic with only a fisherman, a jazz musician and an artist for company. I’d sought out an isolated location, free from distractions to write a book. Even there, the book didn’t get written, and I spent my days kayaking around the archipelago, watching orca, admiring the northern lights and sweating in the sauna.
Want to know more about our amazing guides? Check out our meet the team section on the blog to get to know our team a little bit better and for more expert advice on all things cycling!
