Could anyone hitchhike around 100 Scottish islands in just two weeks?

Inspired by a holiday read while sunning himself on an Algarve beach, our reporter decided he just had to give it a go

• Brian, left, and Jim arriving in Barra

IT SHOULD probably been a plan hatched over a couple of single malts in front of an open fire. But the inspiration for HitchHop, the name we gave our mini-adventure, actually came in the sun-drenched Algarve as I devoured Paul Smith's fantastically addictive book, Twitchhiker.

It recounts his experiences after coming up with the idea of trying to travel to the other side of the world from his native Gateshead using only Twitter for help. I was hooked – on the sheer madness of it, the thrill of the step into the unknown, and the whole premise of relying on the goodwill of others to get around.

It got me thinking about how such a challenge in Scotland would pan out – and whether Twitter and Facebook could help influence such a trip on these shores. As a devotee of Scotland's islands, I spent days trying to come up with potential ways to rethink Twitchhiker for a summer holiday at home with a difference. Before long, two other travel books sprang to mind – comedian Tony Hawks' hilarious attempt to hitch round Ireland accompanied by a fridge and former Scotsman journalist Nick Thorpe's efforts to boat-hitch around Scotland.

Could all three help inspire my own adventure – but one with a twist so daft no-one that would have come up with it before? Eventually, I dreamt up a simple premise – trying to get to as many islands as possible within a set period of time – two weeks. It would have to be a hitch-hiking challenge, as I'd enjoyed at least ten trouble-free years of hitching experience on the west coast. So buses and trains were out, although ferries – for sheer logistical reaons – were in.

From the off, my plans hinged on persuading my good friend Jim Campbell into coming along with me. He was the only friend I judged daft enough to join the fun. He did not disappoint, and diaries were cleared to ensure the end of our challenge would dovetail nicely with the Hebridean Celtic Festival, in Stornoway, a favourite of previous trips. And we knew there was a lighthouse at the very top of Lewis to provide a spectacular finale.

To help drive us on, we decided to support a charity, and the RNLI seemed like the perfect fit for what we were plotting. Thankfully, they embraced the idea and encouraged us to go for broke. As with Mr Twitchhiker, we set five simple rules for what we called HitchHop.

• Both of us have to set foot on an island for it to count.

• All islands will count whether or not they are inhabited – even if they are connected to another island or the mainland by a bridge or causeway.

• Although we will be using ferries, we will be mainly relying on the goodwill of others to get around during the challenge.

• We will accept an offer of a lift, either on dry land or across water, on any form of transport.

• Although we may make some travel plans in advance, we will not accept any lifts until the day we are travelling.

We were deliberately loose in our interpretation of "what is an island?" We were no experts, but to us an island was simply a lump of rock, no matter the size. We also felt it daft to rule out any connected by bridges or causeways to other islands. The trick would still be setting foot on each of them.

A daft idea came to the fore. Our tribute to Tony Hawks and his fridge – a tartan trolley bag, to make us instantly recognisable trying to get a lift. Who else would be travelling the islands with one? I'm also a sucker for a raffle and was convinced a trolley bag would be the perfect travelling companion to cart prizes around in to help our fundraising.

We were reasonably confident about getting lifts on the road, although less enthused about the prospect of standing with our thumbs out in driving wind and rain. Or boat-hitching in gale-force winds. If HitchHop was to be a real success, we needed decent weather.

Although we would be using an unlimited "rover" ticket on Calmac's ferry services, we would have to try boat-hitching if we were to get to more than 30 islands, an initial early estimate. What if no-one let us hop aboard? Would we have to resort to scrubbing the decks to get a lift?

We decided against an official target number of islands, on the grounds that if we got nowhere near we would feel complete failures, while if we passed it easily our challenge could run out of steam.

To help raise awareness of HitchHop, we decided to mount a publicity campaign, launched just over a fortnight before we were due to leave, generating coverage in some weird and wonderful places. Jim's home-made logo was printed onto bright orange T-shirts (the same colour as RNLI lifeboats), as well as hundreds of business cards and postcards. Dunbar RNLI even helped us get our publicity pictures on a training exercise.

Our efforts seemed to pay off and we began to get vague offers of help on Facebook and Twitter. We decided to take our first lift, sailing out of Glasgow on the Clyde, aboard the Waverley paddle steamer, whose future has been threatened by a decline in passengers in recent years, a cause we could easily support online.

We could see a potential pattern developing. But would people really be willing to help us in return for a bit of publicity on Facebook, Twitter and a planned daily blog?

In the end, HitchHop went like a dream. Our big break came with the weather. We had almost two weeks of warm sunshine, when the most trouble we experienced was battles with midges. We slept through the worst spell on a ferry from Tiree to Oban.

Despite an early confidence-sapping wait for a lift out of Largs during its rush-hour – and a struggle to travel the length of Arran in a heatwave – we never had to wait long for a lift, even on the remotest of roads, although our HitchHop banner and an RNLI flag must have been hard to miss. Drivers were full of ideas of how to bag extra islands, many going out of their way to allow us to boost our tally or ensure we caught a ferry on time.

That we managed to get into some vehicles with "Thomas", our increasingly-battered tartan trolley bag, was nothing short of a miracle, especially with the odd dog for company.

We secured a lift with a German family despite their lack of local knowledge: "Where is Hitchhop?" And we were literally running late for a ferry in Berneray in the heat of the day when a motorist who had earlier passed us returned to squeeze us into her hastily rearranged car.

Our big plans to deploy social media to influence us swiftly stalled when we realised how poor phone reception was on the islands. Our blog soon fell hopelessly behind. We had to settle for posting sporadic updates from hostels or libraries.

However, local radio stations were happy to let us on-air to promote HitchHop when we turned up unannounced. We appeared on BBC Alba's news broadcast halfway through the trip, though mercifully did not have to learn to speak Gaelic. And we discovered from friends that word of mouth was spreading around the country.

The main revelation of HitchHop was the boat-hitching element. Russell Cheshire, whose Ocean Breeze company runs tours from Arran's Lamlash Bay, was one of the first to get what we were up to. He let us tag along with one of his tours, which would stop at three destinations to let us hop off and on again – us. We'd never heard of Hamilton Isle until we were about to set foot on it and we'd had no idea that there was an isolated nuns' retreat on the other side of Holy Isle.

In Mull, a visit to the Mishnish pub in Tobermory not only saw us stage a bumper raffle there, but led to an offer of a trip out the following morning with RNLI crew member David McHaffie on a Rib (rigid inflatable boat). By the following lunchtime, another six islands had been notched up, including the tiny Big Stirk, just off Tobermory, which became our favourite island. The pub tactic worked a treat in Islay where two fishermen who had just finished work for the day were cajoled into taking us to two rarely-visited islands off Portnahaven harbour.

However, a visit to Barra – long pencilled into our plans because of the chance to attend the annual "blessing of the boats" ceremony in Castlebay – took things to another level. Off-duty Calmac skipper Michael MacNeil whisked us around than 18 islands off North Bay in his own more modest boat – including a thrilling encounter with a basking shark and a mesmerising lagoon trip – before we returned to Castlebay for a rendezvous with hotel owner John Campbell, who helped us score another nine islands, aided by his trusty broom to help us land on the most hazardous spots.

Single-islands visits often proved entertaining, such as Coll, where we had to quickly persuade a ferryman to relax the rules and allow us to run off the pier and back, or Eriska, where five-star hotel owner Beppo Buchanan-Smith came out to greet us on his carefully manicured lawn, with games of croquet being played a few yards away.

One motorist even insisted we drop in on a sheepdog trials, where by chance we met one of our Facebook followers who ended up providing the crucial contact for our last boat trip.

Various pubs, cafes and hostels became HitchHop HQs for a few hours while phone calls were made, ideas thrown about and raffles conducted. Shopkeepers would happily take a few flyers, pin-up a poster or offer a raffle prize.

Occasionally, someone would have a vague memory of reading or hearing about us somewhere. But with most people, we had to start from scratch.

By the time we reached the Uists and Harris our mobile phone signals were gradually improving. A Facebook plea for last-minute help in Lewis led us to Seatrek, a charter boat company based off Uig, offering the prospect of reaching a dozen or so islands if we could hitch there, which we managed before sunset.

Our morning with Seatrek was an unforgettable experience as their six-man, two-boat crew took us to some 31 islands, jumping on and off at an incredible rate, often clambering over some of the crew to get on to dry(ish) land.

With a full day of the challenge left, we just couldn't leave it at that, despite a group of friends already waiting to greet us in Stornoway.

A chance tea-time encounter at the Co-op with our new Facebook friend from the sheepdog trials secured our passage later that evening on another Rib, with father and son Roddy and Alasdair Maclean. We reached our 100th island just after 9pm at Tannaraidh, with the sun setting over Stornoway in the distance. Somehow, we dragged ourselves along to the opening night ceilidh at the festival, slighly bewildered at what we'd just experienced. I think I fell asleep on the walk home that night. We were praying our luck did not run out on the final day, when all we had to do was hitch the 30-odd miles to the Butt of Lewis. It took just one lift from an SSPCA inspector who recognised us from the ceilidh.

The worst weather of the entire trip, at what it is officially the windiest spot in the UK, kept the champagne on ice at the Butt of Lewis. But over tea and buns in the most northerly cafe in the Hebrides, the thought did cross my mind: "What will next year's challenge be?"

• The Year of Scotland's Islands is a 12-month programme, running until April of next year, showcasing the islands' vibrant culture and creativity, natural environment and quality produce.

l You can support the RNLIL at Brian and Jim's fundraising page: www.virginmoneygiving.com/team/HitchHop