The Historian's Grand Tour – 5000 years of history from ancient stones to Highland clans
I normally guide tours of up to five days, each covering a specific part of the Highlands and Islands. Once or twice a year (subject to availability) I also guide a longer, twelve day private journey – one that brings together many of my own favourite places across the region, tracing five thousand years of history from Neolithic stones to the Highland clans.
The Historian's Grand Tour includes Orkney, the Outer Hebrides, the Isle of Skye and the breadth of the Scottish Highlands. It is the culmination of nineteen years of guiding, and while history runs through the whole route, it also takes in some of the most stunning scenery that the Highlands and Islands have to offer.
One Journey, Five Thousand Years
Each of my signature tours offers a focused route through a single region from Inverness. Yet over nineteen years of guiding, I have come to see the invisible threads connecting them just as clearly as the roads themselves. How a Neolithic tomb-builder in Orkney and a Neolithic tomb-builder in Kilmartin Glen were, in a very real sense, part of the exact same Highland world five thousand years ago – despite sitting over two hundred miles apart. How the Ring of Brodgar and Calanais speak to the very same instinct to mark the land as sacred. How the Picts, who left no written records of their own, carved their presence into stone across the landscape. And how the Highland clans fought, feuded, and endured through the centuries of history.
If I could guide this journey in strict chronological order, I would – but geography dictates otherwise. The Neolithic sites of Orkney and Kilmartin sit at opposite ends of the Highlands, with the Calanais stones on the Isle of Lewis positioned between them. Ferry schedules and driving distances turn us into time travellers: Neolithic by morning, clan history by lunch, Pictish by afternoon, and back to the Bronze Age before day's end. It may not be the tidy timeline one would draft on paper, but history in the Scottish Highlands was never laid down in neat order either.
For all its history, this is just as much a scenic journey as a historical one. The route takes in some of the most dramatic landscapes in the Highlands and Islands – the sea cliffs of Orkney, the beautiful sands of Harris, the mountains of Skye and Glencoe, and the sea lochs of Argyll – so the twelve days are never simply a chain of historical sites. History gives the route its shape, but the scenery is there in equal measure, at every turn.
12 Day Grand Highlands and Islands History Private Tour
- Day 1 — Inverness to Orkney: Departing Inverness, we travel to the ferry port of Scrabster, crossing the Pentland Firth past the iconic Old Man of Hoy to Stromness. The late afternoon is dedicated to Skara Brae, a remarkably preserved 5000-year-old Neolithic village, before we settle into Kirkwall for a three night stay.
- Day 2 — Orkney: We uncover the Neolithic heart of the mainland – the standing stones of Stenness, the monumental Ring of Brodgar, and the 2000-year-old Broch of Gurness – along with the chambered tomb of Maeshowe, the poignant Italian Chapel, and the red sandstone majesty of St Magnus Cathedral in Kirkwall.
- Day 3 — Orkney: A day to venture beyond the main sites – the towering cliffs of Yesnaby, the tidal island of Birsay, and the dramatic Gloup sea cave, or, for those with an interest in naval history, a crossing of Scapa Flow to Hoy and the Scapa Flow Museum.
- Day 4 — Orkney to Inverness: Departing Kirkwall, we head to Stromness for the ferry back to the Scottish mainland at Scrabster. Our return journey follows a beautiful coastal route, with a mid-afternoon visit to Dunrobin Castle, the largest and grandest castle in the Highlands, before we settle back into Inverness for an overnight stay.
- Day 5 — Inverness: We explore Culloden Battlefield and the 4000 year old Clava Cairns before heading east into Moray. Highlights include Sueno’s Pictish Stone, the impressive ruins of Elgin Cathedral and Rodney’s Stone in the grounds of Brodie Castle before returning to Inverness.
- Day 6 — Inverness to Isle of Lewis: We board the ferry for a crossing of the Minch to Stornoway, my home island, where we step back through millennia of Hebridean history at the Neolithic Calanais Standing Stones and the 2000-year-old Dun Carloway Broch, concluding at the secluded beach of Dalbeg.
- Day 7 — Isle of Harris: Crossing into the Isle of Harris, we take in the white sands of Seilebost and Nisabost before visiting Rodel and its remarkable 16th-century tomb carvings at St Clement's Church.
- Day 8 — Isle of Lewis, Harris and Skye: A morning at the Butt of Lewis, the most northerly point of the Hebrides, followed by the Lewis Chessmen at Museum nan Eilean, before a ferry crossing to the Isle of Skye and our arrival in Portree.
- Day 9 — Isle of Skye: We explore the Trotternish Peninsula – the Old Man of Storr, Kilt Rock, and the ancient cattle pass of the Quiraing – before an afternoon at Dunvegan Castle, ancestral seat of Clan Macleod and the oldest continuously inhabited castle in Scotland.
- Day 10 — Isle of Skye to Oban: A ferry crossing to Mallaig leads us along the Road to the Isles to Glenfinnan and its Jacobite monument, before we pass beneath Ben Nevis into Argyll, arriving in Oban for a two night stay.
- Day 11 — Kilmartin Glen and Argyll: We journey through millennia of history in a single day – Kilmartin Glen, a mystical landscape of Neolithic standing stones, burial cairns and stone circles, followed by Inveraray Castle, ancestral home of Clan Campbell, and a viewpoint stop at Kilchurn Castle on Loch Awe.
- Day 12 — Oban to Inverness: On our final day, we explore the haunting beauty of Glencoe and the chronicles of the 1692 massacre, before returning north-east along the Great Glen, pausing at Fort Augustus to watch the Caledonian Canal locks, concluding the tour in Inverness.
Private Tour Price (per tour)
May to September: £10000
Depart Inverness
Return Inverness
(12 Days)
Depart Inverness
Return Inverness
(12 Days)
What's Included
What's included in the tour price?
Tours are exclusively for your private group only (up to 3 persons) and prices are per tour. I only offer private tours and do not combine individuals or separate groups – if your private group size is less than 3 the advertised tour price still applies. Your private tour price includes:
- Private tour for your group only (1, 2 or 3 persons)
- An experienced driver-guide and historian (John Alasdair Macdonald)
- A comfortable tour vehicle with good visibility and generous legroom
- All ferry tickets (I take care of all ferry bookings)
- All taxes and fees
What's excluded?
The tour price does not include your accommodation costs, entrance fees, meals and refreshments.
Where should I book accommodation?
To make the most of your tour I recommend you book accommodation in:
- Kirkwall (Day 1, 2 and 3)
- Inverness (Day 4 and 5)
- Stornoway (Day 6 and 7)
- Portree (Day 8 and 9)
- Oban (Day 10 and 11)
Whilst I do not book accommodation directly, I am always happy to offer advice on where to stay and eat. Your tour quote will include a full list of recommended accommodation options for every overnight location along with suggestions for evening meals.
Route & Logistics
Which days does this tour start on?
This tour is available on Wednesday and Friday start days from Inverness.
Where does the tour start from?
Enjoy the ease of a private pickup – I will meet you directly at your Inverness accommodation on the morning of Day 1 to begin the tour. At the end of the tour I will drop you off at your preferred Inverness location.
Is there a return to Edinburgh option?
Yes, but only on this tour. Given its length, I am able to offer a return to Edinburgh instead of Inverness on the final day – something I do not offer on any of other tours. Rather than returning via the Great Glen, we still visit Glencoe in the morning, but the afternoon becomes a scenic drive south through the Trossachs, arriving in Edinburgh around 3–4pm, where the tour ends at your city or airport accommodation. This option carries a surcharge of £200.
What about the ferry sailings?
Ferry sailings are generally reliable in the summer months, but delays and cancellations can occasionally occur. While I cannot be responsible for additional accommodation, food or other costs that clients may incur due to ferry delays and cancellations, I will make every effort to adapt the tour to minimise disruption. Please note that no refunds will be given for tour and itinerary changes due to ferry changes and cancellations.
Can the tour itinerary be customised?
The tour itinerary is based on nineteen years of guiding experience, previous client feedback, and practical travel timings. However, there is a little flexibility and the itinerary can often be adapted in advance to suit particular interests or requests where possible. Please mention any requests in the 'Extra Information' section when completing a Tour Enquiry Form.
Comfort & Practicalities
How much walking does this tour involve?
Most stops on this route are short walks from the vehicle to a viewpoint, castle or historic site. The pace is relaxed and there is plenty of time to enjoy each stop. If you would prefer to skip a particular walk or explore at your own pace, that is absolutely fine on a private tour.
How often do we stop?
The tour has plenty of viewpoint, photo and refreshment stops along with regular restroom stops. As it is a private tour, we can pretty much stop whenever you want!
What clothing/footwear should I bring?
Walking shoes or sneakers with good grip is recommended, along with a light waterproof jacket as Highland weather can be very changeable. All walks are entirely optional and can be tailored to your comfort and mobility level.
How much luggage can I bring?
The current tour vehicle comfortably accommodates up to three passengers with room in the rear boot (trunk) for one medium bag/suitcase per person and one small day bag/backpack per person. If you are unsure about luggage capacity, please let me know the size of your cases and I can confirm there is room.
Do you help with the luggage?
I am happy to help with your suitcases at each overnight location – some of the smaller hotels around the Highlands and Islands do not have lifts but I will gladly assist in getting your bags to your room.
Booking & Availability
How far in advance should I book?
Because this tour requires twelve continuous days of availability, it is best to enquire as early as possible. I regularly accept bookings up to 18 months ahead.
What are the deposit and payment terms?
A 50% non-refundable deposit is required to secure your dates, with full payment due 60 days before the tour start date. Deposit and balance payments are made securely online and accept Visa, MasterCard and American Express. Full details are available in my Terms and Conditions.
How do I book the tour?
The first step is simply to complete a Tour Enquiry Form with your preferred travel dates. I will then reply with availability and a detailed tour quotation (with absolutely no obligation to proceed at this stage). I usually reply to enquiries within 24 hours.
Can I just chat about the tour before booking?
Of course! Given the scale of this tour, I'm always happy to talk it through before you commit. You can reach me in whichever way is easiest for you:
- Complete a Tour Enquiry Form – just ask any questions in the 'Extra Information' section.
- Email me directly at info@thehebrideanexplorer.com.
- Send a WhatsApp message or call me on +44 7943 863292.