A Journey to The Western Isles

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This is the story of two old, grumpy men embarking on a cycling journey, retracing the footsteps of two other, far more famous grumps—Samuel Johnson and James Boswell in 1792.

In our journey, nobody died, no major disasters happened. Nobody got murdered (although sometimes it was pretty close). While our tale may not have been national headlines, it is not without merit. Over three weeks, we visited seventeen Scottish islands, gathering stories and memories along the way. So, cosy in and let me recount our adventure.

Lets start with ME...ME...ME...

Well, I would never claim to be a long-distance cycling superhero. In fact, before this project, setting out on a cycling adventure was nowhere near the top of my 'to-do” list. As a teenager, I rode my bike primarily out of necessity rather than enjoyment, and in the years since, I’ve taken a far more leisurely form of transport.

Four decades have slipped by my only real connection to cycling being the annual tradition of watching the Tour de France from the comfort of my armchair. So, what drove me to undertake such a journey? It may have been a blend of midlife bravado and a desire to prove I could still accomplish something physically significant before my hips, knees, or mind reached their expiration dates.

West with Weston

When it came to choosing a companion, my ego couldn’t risk being outdone, so I needed someone whose fitness matched—or perhaps fell just short of—my own. Chris a long-standing friend from my sailing days fitted this description perfectly. Though I might have started out as the (slightly) fitter of the two, as the journey unfolded, Chris demonstrated remarkable mental resilience and a quietly persistent spirit. His tall, lanky silhouette, paired with a determined grin as he pushed his bike up (and, YES, down) the Scottish hills, said everything about his ability to stick with a challenge — especially since we were battling some truly awful weather along the way.

This tale is dedicated to my cycle partner Chris Weston, despite what I might say about him in the first few chapters, his determination and uncomplaining attitude shone through. It was a pleasure to ride with him.

LE-JOG or JOG-LE

Our original plan was to tackle LEJOG—the iconic Lands' End to John O'Groats cycle route, famed among touring cyclists. At this point, I only considered myself a touring cyclist largely because I now owned a touring bike. But, as Robbie Burns so aptly put it, "The best-laid plans o' mice an' men gang aft agley." And, indeed, our plans did go 'agley'.

Logistical challenges quickly surfaced with the LEJOG route. Lands' End lies 430 miles from my home in the East Midlands, and even after reaching the far tip of Cornwall, we would have to double back nearly all the way to central England before heading north. What seemed an easier and more appealing alternative was to cycle 500 miles through the Outer Hebrides, visiting as many Scottish islands as we could along the way.

Ultimately, we traversed 17 islands, and both of us narrowly survived the midges and trench foot!

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'Be Prepared'

Chris is, without question, the most pleasant and unassuming insurance man I have ever met. His days are filled with work and an array of community responsibilities, leaving him precious little time for personal pursuits.

Remarkably, just ten weeks before our great adventure was to commence, Chris still hadn’t acquired the most essential piece of equipment—a bike. This led to a frantic eBay bidding war, and a hasty purchase made without any real consideration of its worth. Retrieving the bike required a long journey to Cheltenham, after which it was quickly handed over to the local shop for an expensive full overhaul.

Months of detailed planning and preparation had all fallen to me, as had the careful testing of our equipment. With time to spare, I was ready and packed, but Chris had me dashing around Leicester to collect last-minute bits and pieces: a lightweight sleeping bag, spare parts for his bike etc. Amongst this was a rather smart camping cutlery set I bought for £1.99. It came in a stylish black canvas holder and seemed to have magical disappearing qualities.

Chris had also assured me that the hiking tent he’d bought from a ‘Toys-Are-Us’ closing down sale was ‘fit-for-the-purpose’. I should have been more inquisitive. It turned out that he hadn’t even opened the bag since buying it. Unlike Chris, I had taken my own tent for a dry run (which, ironically, was anything but dry, it had a good soaking) to St Neots, Cambridge. That weekend trial taught me that anything more complicated than boiling a cup of coffee was out of the question; my tent was simply not designed for culinary feats. On returning home, I threw out the Cordon Bleu Campers Cookbook. Even my shaving kit fell victim to my quest for efficiency, as I repeatedly crossed it off, only to give up and grow a beard instead.

. . . and their OFF!

And so, in September 2008, two novice, utterly unprepared, cycle-tourers—set off into the Scottish outback, in what would prove to be the wettest summer since...well, since 2007.

The drive up the A1 to Edinburgh was the usual nightmare journey. Enough said. Our base camp would be my mother’s house. On arrival, Chris spent the evening packing his panniers, a task he hadn’t even begun when I picked him up that morning. He rushed around his house emptying his wardrobe into the back of my car in a mild panic of clothes collecting. That evening, to my dismay, he started making a lengthy list of items he still needed to buy before we could embark on our journey into the unknown.

Camera Shy

One crucial item Chris realised was missing was his new, expensive digital camera— the one special purchase he had made just before our planned departure. As we sifted through the luggage scattered across my mother's living room, it became clear the camera was nowhere to be found. Retracing his steps, Chris recalled taking it to his gym shortly after buying it. He distinctly remembered last seeing it in his kit bag, which now appeared to have suspiciously gone-walk-about. Typically, a law-abiding and mild-mannered person, Chris was furious at the loss. His calls for justice—directed not only at the culprit but at the entire membership of the Sport Centre—were delivered with the fervour of a zealous crusader.

A major expedition on day one was a visit to the shops in Princess Street.

Tiso's are for heroes, like us!

Saturday morning saw us darting through the shops on Edinburgh’s Princes Street, especially Tiso’s—a haven for the heroic adventurer. If you are a Munro bagger, you do it outfitted in Tiso’s gear. Skiers, canoeists, and climbers flock there for the latest outdoor essentials and, more importantly, to parade the season’s fashionable colours around the Scottish hills. Unfortunately, for us, the camping section is on the top floor, and it was like climbing the north-face of the Eiger. By the time we reached it, we were both breathless, a fact clearly not lost on the smug, muscle-bound shop assistant looking on. Chris wasted no time gathering clothes, emergency packs, midge nets, and, of course, the requisite Avon 'Soft and Gentle'.

This afternoon, we were set to leave for the 'wild west nether regions' of Glasgow.