The Grand Highlands and Islands Tour

The Best of the Highlands and Islands, in One Journey

Each of my signature tours offers a focused route through a single region from Inverness – Skye, Orkney, Shetland, the Outer Hebrides – each with its own character and story. This tour exists because, after nineteen years of guiding, I kept coming back to the same thought: what if there was one journey that brought all of it together?

The route inevitably jumps around a little in time and place – geography, ferry schedules and driving distances make sure of that. One afternoon we're standing among five-thousand-year-old standing stones, the next we're inside a clan castle still lived in today, and the one after that we're on the northernmost tip of Britain looking out at nothing but sea. It isn't a tidy, chronological story, but then Highland and island history was never laid out that way either.

For all of that, this is just as much a scenic journey as a historical one. The route takes in some of the most dramatic landscapes anywhere in Scotland – the sea cliffs of Orkney, the white sands of Harris, the mountains of Skye and Glencoe, and the wild coastline of Shetland – so the twelve days are never simply a chain of sites to tick off. Landscape, culture and history all share the stage here, in more or less equal measure.

In practice, this tour is built from two routes I already know well. The first five days follow a slightly modified version of my 5 Day Outer Hebrides and Isle of Skye Tour, and the remaining seven follow the same route as my Orkney and Shetland combination, linking two journeys I have guided many times before into one continuous twelve days.

12 Day Grand Highlands and Islands Private Tour

• Day 1: Inverness to Isle of Lewis: — Departing early from Inverness, we travel to the coastal village of Ullapool to board the ferry for a 2¾ hour crossing of the Minch. Arriving in Stornoway on the Isle of Lewis (my home island), we spend the afternoon stepping back through millennia of Hebridean history. We explore the magnificent Neolithic Calanais Standing Stones, the formidable 2,000-year-old Dun Carloway Broch, and the traditional thatched blackhouses that once sheltered island families for generations. We conclude our first day at the secluded Atlantic beach of Dalbeg before returning to Stornoway for our overnight stay.
• Day 2: Isle of Harris — Heading south from Stornoway, we cross the mountain border into the Isle of Harris. The drive along the Atlantic coastline reveals the breath-taking white sands and turquoise waters of Seilebost and Nisabost. At the southern tip of the island, we visit Rodel to explore the medieval St Clement’s Church – home to one of Scotland’s most remarkable 16th-century tomb carvings. After a late afternoon pause in the ferry port of Tarbert, we journey back through the rugged North Harris hills to Stornoway for our overnight stay.
• Day 3: Isle of Lewis, Harris and Skye — We spend the morning at the Butt of Lewis – the most northerly point of the Hebrides – where a lonely lighthouse stands guard over towering cliffs and the crashing Atlantic waves. Returning to Stornoway, we visit Museum nan Eilean within the gothic splendor of Lews Castle to see the world-famous Lewis Chessmen. In the afternoon, we travel south to Tarbert to board the ferry for a 1¾ hour crossing to the Isle of Skye, before our slightly later arrival (approx. 7pm) in the colourful harbour town of Portree for our overnight stay.
• Day 4: Isle of Skye — From Portree, we explore the Trotternish Peninsula, pausing for views of the Old Man of Storr and the coastal cascades of Kilt Rock. We then ascend the ancient cattle pass to the Quiraing; looking out over the village of Staffin toward the Northwest Highlands, this remains a definitive highlight of the Isle of Skye. After a visit to the Museum of Island Life at Kilmuir, the afternoon is dedicated to Dunvegan Castle. As the ancestral seat of Clan MacLeod and the oldest continuously inhabited castle in Scotland, it offers grand history and exquisite gardens to explore before our return to Portree.
• Day 5: Isle of Skye to Inverness — Departing Portree, we journey south to the Sleat Peninsula, an area of stunning coastlines and heather-clad hills often missed by the crowds. Known as a quieter side of Skye, it offers secluded roads and hidden vistas that larger tour buses simply cannot reach. We pause at Isleornsay for views across to the Knoydart wilderness before exploring the breath-taking western shores of the peninsula. After a final morning of unhurried discovery, we begin our scenic return journey through the Highlands to Inverness.
• Day 6: Inverness to Orkney — Departing Inverness with a morning drive to the far North of Scotland and the ferry port of Scrabster near Thurso. The drive north covers wonderful coastal scenery and normally takes around 3-4 hours including photo stops and a brief visit to the historic town of Dornoch. Our 1½ hour ferry journey across the Pentland Firth to Orkney includes a great view of the Old Man of Hoy before our arrival in Stromness. The mid-afternoon is focused on a tour of Skara Brae, a stunning 5000 year old Neolithic village settlement – one of the highlights of the trip to Orkney. We end the day with a short drive to Kirkwall for our overnight stay.
• Day 7: Orkney — Our first full day in Orkney includes a visit to Maeshowe Neolithic chambered tomb. We also explore the Neolithic standing stones of Stenness, the Ring of Brodgar and the 2000 year old Broch of Gurness. The afternoon takes us to the Italian Chapel and the Churchill Barriers before our return to Kirkwall for our overnight stay.
• Day 8: Orkney — Our second full day on Orkney provides the opportunity to venture beyond the main sites. We can focus on Orkney's dramatic coastline, visiting the towering cliffs of Yesnaby, the tidal island of Birsay, and the Gloup, a dramatic collapsed sea cave in Mull Head Nature Reserve, along with free time in Kirkwall or perhaps a tasting at the Highland Park or Scapa whisky distilleries (advance booking required). Alternatively, for those interested in Orkney's naval history, we can sail across Scapa Flow to the Isle of Hoy, visiting the acclaimed Scapa Flow Museum along with the secluded, towering cliffs of Rackwick Bay. After dinner in Kirkwall, we take the overnight ferry (departing at 11.45pm) to Shetland.
• Day 9: Shetland (South Mainland) — After breakfast on board as we sail into Lerwick, we spend our first day exploring the South Mainland. We visit the towering cliffs of Sumburgh Head, a spectacular haven for seabirds and puffins, before delving into the archaeological layers of Jarlshof. This extraordinary site reveals a sequence of island life spanning from the Bronze Age to the Norse era. We conclude the afternoon at St Ninian’s Isle, where you can walk across the world-famous sand tombolo set against the Atlantic waves.
• Day 10: Shetland (Isle of Unst) — Today we journey to the very northern edge of the country: the Isle of Unst. After two short ferry crossings via the Isle of Yell, we reach the most northerly inhabited island in Scotland. We spend the day exploring a landscape of Norse heritage and wild geology, visiting the ruins of Muness Castle and the dramatic shores of Burra Firth. From the heights of Saxa Vord, we look out towards Muckle Flugga lighthouse – Scotland's northernmost point – before making our scenic return journey to Lerwick.
• Day 11: Shetland (North Mainland) — We head to the wild North Mainland to witness the sheer power of the Atlantic at Eshaness. Here, the dark volcanic cliffs and jagged sea stacks offer some of the most dramatic coastal scenery in the islands. We then tour the ancient capital of Scalloway and the picturesque islands of Burra, connected by bridges to the mainland. After a visit to the award-winning Shetland Museum in Lerwick to explore the islands' maritime history, we board our overnight sailing (in the mid-to-late afternoon) back to the mainland.
• Day 12: Aberdeen to Inverness — Arriving into Aberdeen harbour in the early morning (7am) we enjoy a leisurely breakfast on the ferry before heading east towards to Elgin to explore the stunning 700 year old ruins of Elgin Cathedral and the Pictish standing stones of the area. The afternoon takes us back to Inverness where we end the tour with a visit to the 4000 year old burial cairns and standing stones at Clava followed by a guided walk of Culloden Battlefield.