Just the epic island-hopping journey he had in mind
When Arlen contacted us with dreams of experiencing Scotland’s wild islands and remote Highlands, we found a kindred spirit. Arlen was seeking an authentic journey that would take him beyond the tourist trails to discover the raw beauty of the Hebrides and the dramatic landscapes of the Highlands. We crafted a tailor-made 20-day adventure that combined island exploration by car, cycling the legendary Hebridean Way and enjoying peaceful moments travelling by rail in Scotland’s most remote corners.
Arlen’s brief
- Male, solo traveller from New Zealand
- 2-3 weeks to spend in Scotland in April as part of a 3-month sabbatical in Europe
- Likes the idea of bikepacking and staying in guesthouses, farmstays and hostels
- Previously did a rail tour around Edinburgh – Stirling – Inverness – Aberdeen, where he enjoyed seeing the mountains from the train
- Now wants to get out and explore in more detail at a slower pace, possibly hiking or cycling
- Enjoys walking and cycling but is not a regular cyclist
- Very keen to explore the Outer Hebrides
- Agreed a combination of self-drive, rail and cycling would be perfect
- Really likes historical sites, not just castles
Day 1: Exploring Glasgow
Arlen’s Scottish adventure began with his arrival into Glasgow, where he began gently by exploring the architectural treasures of Rennie Mackintosh. We knew this cultural immersion would be the perfect prelude to the wilderness adventures ahead. Our choice of 4-star hotel, acclaimed for its approach to sustainability, provided him with comfortable city accommodation before his journey into Scotland’s wilder territories. This gave him time to adjust and anticipate the island adventures we’d planned.
Day 2: Glasgow to Oban by rail
The adventure truly began as Arlen boarded the scenic train from Glasgow to Oban. This journey is renowned for its breathtaking views across lochs and mountains. We’d timed his arrival perfectly to allow an afternoon exploring Oban’s famous seafood scene and harbour atmosphere. The family-run guesthouse became his base, where we knew the welcoming hosts would share local insights and prepare him for the island explorations we’d carefully curated.
Day 3: Discovering Mull, Iona & Staffa
Day three brought the island adventure Arlen had been dreaming of. We’d arranged for him to join a bus, ferry and boat tour of three nearby islands, taking him through Mull’s dramatic landscapes before the short ferry crossing to sacred Iona—a place we knew would capture his spiritual side. The journey continued to the wildlife haven of Staffa with its famous basalt columns and Fingal’s Cave. In the late afternoon, he then returned to Oban giving him time to reflect on the day’s discoveries.
Day 4: Sailing from Oban to Castlebay
It was time for the long crossing from Oban to Castlebay on the island of Barra. This 5.5-hour voyage through the Inner Hebrides was something we knew would transition him from mainland Scotland into true island life. His accommodation at the local hostel wasn’t just about budget-friendly lodging; we’d chosen it for its authentic island atmosphere and the connections he’d make with like-minded adventurers.
Day 5: Driving across Barra
Arlen’s real Hebridean exploration began as he collected his hire car (self arranged) and set off across Barra. Based on our own travels through the islands, we knew the perfect combination of walks and drives to suggest, knowing his love for coastal scenery would be perfectly matched by the 9km northern peninsula circuit and the stunning beaches of Vatersay. The causeway crossing to Vatersay revealed exactly the kind of hidden gem we’d promised, a 7km circular walk through one of Scotland’s most pristine coastal landscapes.
Day 6: Exploring South Uist
The island-hopping adventure continued as Arlen took the short ferry to Eriskay, where we’d suggested he keep watch for the wild ponies that roam free. We’d planned his route through South Uist, providing him with walking options from the gentle 6km Bornais circuit to the challenging 20km Beinn Mhor adventure, choices that meant he could match his daily energy (and the local weather!) to the landscapes that called to him.
Day 7: Discovering Benbecula
We’d suggested Arlen experience one of Scotland’s small distilleries on Benbecula and prompted a visit to a wonderful community café we know and love, knowing his appreciation for authentic local experiences would be perfectly served by these local hidden gems. His journey north to the pristine sands of Tràigh an Iar beach and the wildlife haven of Balranald RSPB Reserve fulfilled his sense of adventure for the day, providing him with opportunities to stretch his legs and spot for wildlife in the skies above.
Day 8: Walking around Berneray
The final day of Arlen’s Southern Hebrides exploration took him to Berneray, where we’d suggested a final walk around the popular 12km coastal circuit, an interesting mix of Hebridean machair, boggy hill ground and the pristine sands of West Beach! A local bunkhouse provided authentic island accommodation to complete his Southern Hebrides immersion and a chance to meet travellers freshly landed from the islands’ northern counterpart.
Day 9: Cycling the Hebridean Way
Arlen’s transition from Southern to Northern Hebrides marked a new chapter in his adventure. Leaving his hire car behind, he made the ferry crossing to Leverburgh on Harris as a foot passenger, ready to begin the next stage on two wheels. Swapping his luggage for the hire bike we’d arranged, Arlen set off pedalling the Hebridean Way while his bags were swiftly whisked away to his hotel in Tarbert, 35km away. This first cycling day, with its dramatic coastal views and rolling Harris landscapes, was exactly the kind of active adventure we knew would energise him for the challenges ahead.
Day 10: Harris & Lewis on two wheels
The second day of Arlen’s Hebridean Way cycling took him from Tarbert to Balallan, a 34km journey through some of Harris & Lewis’s most spectacular scenery. We’d chosen a family-run B&B not just for its comfort, but for the hosts’ willingness to provide evening meals and packed lunches – a simple but essential offering in such a remote place and the kind of flexible, personal service that transforms a good trip into an exceptional one.
Day 11: Cycling the final stretch
We’d planned this 50km cycling day as the crescendo of Arlen’s Hebridean Way experience. The route from Balallan took him past the ancient Calanais standing stones, an unmissable and magical landmark from Scotland’s mysterious past. His arrival at the local hostel in North Bragar marked not just the completion of his cycling challenge, but his entry into Lewis’s wild northwest coast.
Day 12: Self-drive tour of Lewis
Recognising that Arlen deserved some flexibility after his cycling achievement, we’d arranged a private transfer to Stornoway where he could return his bike and collect a hire car. The drive to the Butt of Lewis lighthouse gave the wild, windswept experience he’d been seeking, while the 6.5km circular walk to Europie beach delivered exactly the dramatic coastal scenery that makes Lewis unforgettable. For the rest of his day, we’d mapped out a self-drive tour of the stunning west coast beaches, including Borve, Dailbeg and Dalmore, knowing each would offer a different perspective on Outer Hebridean beauty.
Day 13: Exploring Lewis’s beaches
Arlen’s exploration of Great Bernera showcased our love for hidden gems. We’ve explored this lesser-known island ourselves and knew he’d love the 11km coastal walk to Bosta beach and its Bronze Age dwelling – a typical Hebridean mix of incredible hiking and fascinating history. Later, the drive around the Uig peninsula to beaches like Kneep, Reef, and Mangersta (our personal favourite) demonstrated exactly why we’d structured his itinerary to end with Lewis’s most spectacular coastal scenery. It also led him to one of our favourite cafes, a true gem that quite literally feels like it’s on the edge of the world!
Day 14: Exploring Stornoway before sailing to Ullapool
We’d planned Arlen’s departure from the islands with the same care as his arrival. His final morning exploring Stornoway and the trails around Lews Castle provided a gentle conclusion to his island adventure, before the afternoon ferry to Ullapool marked his transition back to the Scottish mainland. The crossing itself is part of the experience, providing a time to reflect on the extraordinary island journey we’d crafted together.
Day 15: Driving through Garve and Kyle of Lochalsh
Arlen’s entry into the northwest Highlands began with a scenic bus and rail journey from Ullapool to Garve and on to Kyle of Lochalsh. Collecting his hire car and driving the famous Bealach na Bà pass to Applecross village represented everything we’d promised about Scotland’s dramatic landscapes. Applecross is a special place, one that’s dear to our own hearts, and we knew he would appreciate the peace and relaxation it would offer after his island adventures.
Day 16: Walking around Applecross
We’d built this rest day into Arlen’s itinerary knowing that even the most adventurous spirits need time to absorb and reflect. The choice of walks from Applecross village, including the stunning coral beaches, meant he could be as active or contemplative as his mood demanded. The local hostel provided exactly the kind of comfortable, no-frills accommodation that suited his independent travel style, yet still within walking distance of the village’s beloved inn.
Day 17: Visit to Torridon’s dramatic mountains
The drive along Applecross’s spectacular coast road to Torridon provided a relaxing day out while showcasing one of Scotland’s most scenic routes. We’d recommended the Applecross Smokehouse knowing Arlen’s appreciation for local artisan produce, while the visit to Torridon’s dramatic mountains and the charming Wee Whistlestop Cafe provided a choice of epic adventure or gentle relaxation, depending on how the mood took him on the day.
Day 18: Kyle of Lochalsh to Inverness by rail
Arlen’s journey from Applecross back over the mountain pass to Kyle of Lochalsh, then by train to Inverness, was the perfect transition from remote highlands to Scotland’s Highland capital. His accommodation in a local ‘bar with rooms’ run by a fellow B Corp provided comfortable city accommodation while maintaining the authentic Scottish character that had defined his journey. It also just happens to serve its own delicious organic beers and they make pretty awesome pizza too!
Day 19: Exploring Inverness
We’d crafted Arlen’s Inverness day with optimal flexibility, providing suggestions such as a boat trip on the famous Loch Ness or enjoying a simple walk around Ness Islands. The afternoon train to Pitlochry and evening exploring this charming town provided the gentle conclusion his highland adventure deserved, with the local hostel offering comfortable accommodation in stunning Perthshire surroundings.
Day 20: Discovering Pitlochry
Arlen’s final day perfectly balanced relaxation with optional adventure. Whether choosing one of our suggested local hikes from Pitlochry or taking the short train ride to visit impressive Blair Castle, he had the flexibility to end his journey exactly as he wished. The afternoon train to Edinburgh brought his 20-day tailor-made Scottish adventure to a close, leaving him with memories of islands, highlands and incredible experiences that would last a lifetime.
Plan your personal adventure
This tailor-made 20-day journey is just one example of our expertise in carefully curating complex, multi-destination adventures that seamlessly blend active exploration with authentic cultural immersion. From island-hopping through the Hebrides to cycling the iconic Hebridean Way and exploring Scotland’s most remote highlands, every detail was carefully planned to deliver the kind of transformative adventure that created lifelong memories for Arlen to treasure.
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