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Selected Trips

    Guide Jessie looks into the camera against the dramatic and remote landscape of North Wales.

    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.

    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.

    When I’m not outdoorsying, I am a keen photographer and gardener and am currently trying to learn Icelandic (with difficulty) – þetta reddast!

    Places to Play

    Skye, for the bonkers logistics of trying to get from one side to the other.
    The Isle of Arran for sampling Scotland in miniature and the incredible Cìr Mhòr ridge.
    The Cairngorms for the sweeping roads and quaint little forests near Balmoral.
    Rum – a destination that’s been on the list for years!

    Not a Lot of People Know This

    I once drove a motorhome between all of the national parks in Scotland on a continuous 20 day challenge and thought the Cairngorms was one of the best places ever to visit in a motorhome – they have great lay-bys and tea shops.

    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

    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 in Tynemouth two days later…

    Specialist Subject Read More

    I enjoy researching women mountaineers who contributed towards a relatively unknown corner of outdoor history and writing. I’m a big fan of Nan Shepherd, Gwen Moffat, and Dorothy Pilley – some amazing stories of what they got up to when it wasn’t appropriate for a woman to run around in the mountains without a skirt on.

    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 Advnture.com, 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
    Wilderness Walking – High Points of the Lake District
    13th Jul - 18th Jul 2024
    Trip FullFULLY BOOKED £1,895

    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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