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Jessie Leong

Jessie Leong

Creative | Engaging | Empathetic

Mini Bio

I have been an outdoor instructor for over ten years, working as a freelancer teaching navigating, route planning, expedition management, and bushcraft survival skills. I regularly travel to Northern Iceland in the winter season to guide snowmobiling, snowshoeing, cross country skiing, and paddle sports.

My favourite thing about guiding is meeting many different people from around the world. I love nothing more than having a laugh and sharing a cuppa and a chocolate biscuit by the fire. I am a keen cold-water swimmer, mountaineer, and rock climber. I am also currently trying to master the dark art of ski touring.

Having spent time juggling outdoor work alongside creative projects, I am also an award-winning filmmaker. One of my climbing films won People’s Choice at Kendal Mountain Film Festival. My most recent film, Perfect Partners, was shown as part of Montane’s International Women’s Day. You can watch the films on my YouTube Channel.

Favourite Place to Play

Anywhere in the Chew Valley, Peak District
West Cornwall, ideally the rock climbing on Bosigran
Going for a gorgeous hike through the meadows in the Yorkshire Dales and eating all the cheese samples

Not a lot of People Know This

I play a Miss World contestant, Miss Philippines, in the film Misbehaviour (2020) about the 1970s Miss World contest.

Qualifications Read More
  • Mountain Leader (Summer)
  • Rock Climbing Instructor
  • Outdoor First Aid (16hr)
Experience Read More

Having done many hiking expeditions, from exploring the Caucasus in Georgia to the Fann Mountains in Tajikistan to the foothills of the Himalayas, I have enjoyed exploring the far-flung corners of the world, learning to be adaptable, to be thankful and gracious, to plan ahead, and, above all, to have a happy and positive outlook on life – being able to hold onto your plans loosely helps!

Biggest Adventure Read More

Most of my adventures centre around the communities that have done a lot in gaining experience in the outdoors – I’ve done many adventures with a hillwalking and mountaineering club, and I’m also part of the Pinnacle club, a women’s only climbing club and the Alpine Club.

But the biggest adventure has to be when I took my Dad (67 years old) on an unsupported road ride along the Hadrian Cycleway. We had a mechanical failure 14.5 km/9 miles east of Carlisle on a Sunday with no bike repair shops nearby. Somehow, we managed to blag a free bike, two cups of tea, and a stranger offering to post my Dad’s broken bike back home. We made it to the end of the cycleway!

Specialist Subject Read More

I am a big fan of the literary greats, and when I was younger, I was convinced that Elizabeth Bennet was my teen hero.

Publications Read More

I’m a features writer for Summit Magazine, one of the UK’s largest outdoor magazines for hillwalkers, climbers, and mountaineers. I write regularly for, with work published in Nat Geo, Sidetracked Magazine, and on BBC News.

Book a trip with Jessie

Trip / DepartureAvailabilityStatusPriceBook
Luxury Walking – Highlights of Northern England
2nd Jul - 11th Jul 2024
4 place(s) leftGuaranteed 4,295Book Now

Make Trip Private

Sometimes it's nice to get family and friends together and travel privately for some quality time. This means you benefit from all the features of the group departure, including hand-picked accommodation and expert local guides and we'll take care of it all. Then you can make your choice of departures dates and we'll get back to you to finalise the details.

We work together with our team of guides to decide which departures they lead each year. As part of that, guides provide available dates that they are free to be booked. This means that any of the dates you see in the first field of the form below, could be perfect for your private departure or customised tour.


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