Join Mark Bibby Jackson on a 10-day Scotland adventure from Whitby to the Isle of Skye and back, exploring Scotland’s rugged Highlands, historic towns, castles, whisky distilleries and stunning landscapes.
This journey blends history, culture and a touch of serendipity, making it perfect for independent travellers over 40 who love to go at their own pace. Follow along as we uncover hidden gems, iconic landmarks and unforgettable experiences on the ultimate Skye road trip. See what Mark and his three friends from across the Pond – one on his first trip overseas – got up to by following the series of articles below.
Scotland Adventure I: Whitby, Bamburgh and Holy Island
Link: Read Part I
Mark takes friends and family from the North York Moors to historic Whitby, exploring Dracula’s Abbey, Bamburgh Castle, and Holy Island before heading to Edinburgh. Highlights include moorland views, coastal scenery, and local fish and chips.
Scotland Adventure Part II: Portobello, Kelpies and Cairngorms
Link: Read Part II
Skirting Scotland’s cities, the journey heads along the scenic A9 through the Cairngorms. Stops include Portobello Beach, The Kelpies, Pitlochry, and Culloden Battlefield. Whisky tastings and Highland landscapes make this leg unforgettable.
Scotland Adventure Part III: Fairy Pools, Whisky and Wild Landscapes
Link: Read Part III
Finally reaching Skye, the adventure focuses on the island’s dramatic scenery, the Fairy Pools, and local whisky distilleries. Highlights also include Strathpeffer Spa Town, Ullapool’s coastal route, and Fort William for a taste of Highland life.
Scotland Adventure Part IV: Glencoe to Hadrian’s Wall and Chester
Link: Read Part IV
On the journey home, the road winds through Glencoe, past HMNB Clyde (home of Polaris submarines), along Hadrian’s Wall, and ends in Chester. This final leg combines history, Roman heritage, and medieval city charm, rounding off the trip perfectly.
Over to You
Planning your own Scotland adventure? Start with our full Road Trip to Skye travel guide for tips, itinerary ideas and inspiration to explore the Highlands, Skye and beyond. You’ll never look back – trust us.
Photograph of Glencoe taken by Lesley Perlman.
