A Drive Through Scotland
Charles & Catherine Maguire
Sunday 14th September – Sunday 28th September 2025
Overview
Enjoy the best of Scotland as you hit the road to explore the very best that Scotland has to offer. Start off in Glasgow, a vibrant, cultural city that offers a real blend of history and lifestyle. Then it is time to explore the beautiful and remote locations of Oban, The Isle of Skye and Orkney. You will get out on the waters, meet locals, and see and learn the history that these locations hold. It is then time to explore the capital of Scotland, Edinburgh. Arguably one of the most historic cities in Europe there is lots to see and of course the legendary castle that stands high above the city.
Day by Day
Day 1 - Sunday 14th September - Welcome to Scotland
On arrival at the airport you will be met by a private driver who will transfer you to your city centre hotel. Depending on your arrival time you can choose to relax at the hotel or head out to start exploring this unique city.
Overnight: Glasgow | Kimpton Blythswood Square
Room Type: 1x Premium Room
Meals Included: None
Day 2 - Monday 15th September - Glasgow Private Walking Tour & Free Afternoon
Explore the highlights of the city on a private walking tour with an expert local guide. Discover the stories tied in with the varied architecture of streets that have been home to all kinds of creatives over the years. See the influences of Charles Rennie MackIntosh and admire the popular contemporary graffiti murals tucked into unexpected corners all over the city. Your guide will depart at lunchtime, leaving you to continue with further city explorations at your own pace.
Overnight: Glasgow | Kimpton Blythswood Square
Room Type: 1x Premim Room
Meals Included: Breakfast
Day 3 - Tuesday 16th September - Glasgows Varied Food Scene
Today head out with a local city guide and explore some of Glasgows vibrant and varied food. You will visit iconic locations as well as the hidden gems that often produce the most memorable experiences. Learn about the history and what makes Glasgows food scene so appealing as your guide shares their extensive knowledge.
Overnight: Glasgow | Kimpton Blythswood Square
Room Type: 1x Premium Room
Meals Included: Breakfast
Day 4 - Wednesday 17th September - To the Scottish West Coast
This morning you will collect your rental car and depart Glasgow for the beautiful west coast of Scotland. On your journey enjoy the beautiful scenery as you travel through ever changing landscapes on your way to Oban.
Overnight: Oban | No.26 By the Sea
Room Type: 1x Gorgeous Room with Balcony
Meals Included: Breakfast
Day 5 - Thursday 18th September - Out on the Water
Meet a local guide and head out on a days adventure on the water. You will explore some of the small islands off the west coast of Scotland as your guide gives you a brief history of these fantastic locations. If you’re lucky you might come across some of the aquatic wildlife that calls the area home. You could encounter seals, sea birds, and maybe even dolphins as you explore this beautiful coastline.
Overnight: Oban | No.26 By the Sea
Room Type: 1x Gorgeous Room with Balcony
Meals Included: Breakfast
Day 6 - Friday 19th September - To the Isle of Skye
Today you travel to arguably the most famous of Scotland’s Hebridean islands – Skye. You will pass through stunning scenery as you work your way past glistening lochs, stunning mountain tops, and famous castles, until you reach the famous bridge connecting mainland Scotland to the island.
You could opt for a stop at he renowned Eilean Donan Castle, known for it’s role in movies and TV shows, as well as being one of the most photographed locations in Scotland*.
*Entry to the Castle is not included in the trip cost. Tickets should be purchased by the client themselves.
Overnight: Portree | Marmalade Hotel
Room Type: 1x Superior Double
Meals Included: Breakfast
Day 7 - Saturday 20th September - Exploring the Misty Isle
Meet an expert local guide, born and bred on Skye, and head out on a full days exploration of the island, seeing some of it’s most famous locations, alongside some of the hidden gems that only true locals of the island know about. This luxury tour will give you a true insight into life on the island as you lean about it’s rise to becoming one of the hottest tourist spots in the world.
Overnight: Portree | Marmalade Hotel
Room Type: 1x Superior Double
Meals Included: Breakfast
Day 8 - Sunday 21st September - Towards the North of Scotland
Today bid farewell to Skye as you transfer back onto mainland and head for Invergordon. Enjoy the stunning views as you pass Loch Carron and its surrounding beauty. Upon arrival at your accommodation, take some time to relax before an early start tomorrow to catch your ferry to Orkney.
Overnight: Invergordon | Kincraig Castle Hotel
Meals Included: Breakfast
Day 9 - Monday 22nd September - The Ferry to Orkney
This morning, head out for the north coast of Scotland and Scrabster. Here you will board your ferry across to the archipelago of Orkney. Enjoy stunning views out to sea and back across to the Scottish mainland coast as you sail off towards this historic location. Steeped in history, with particular ties to the Neolithic times, there is lots to see during your time here.
Overnight: Kirkwall | The Foveran Hotel
Room Type: 1x Double Room - Kingsize
Meals Included: Breakfast
Day 10 - Tuesday 23rd September - Classic Orkney
Today is a chance to see how the local sheep help to kit out the people that call the island home. Visit a local wool shed and see the processes behind creating warm jumpers from the sheep that are dotted around the island.
You will then have some time to explore at your own pace and head for one of the many historical sites that exist here. One option would be to head for the Italian Chapel, recently voted as one of Orkney’s best visitor attractions*.
*Entry into the Chapel is not included in the price of the trip.
Overnight: Kirkwall | The Foveran Hotel
Room Type: 1x Double Room - Kingsize
Meals Included: Breakfast
Day 11 - Wednesday 24th September - Exploring Orkney
Head out for the chance to truly see Orkney with an expert local guide. You will get the chance to see the very best of the archipelago while learning the history that goes alongside it. There are a plethora of things to see that can be discussed with the guide to ensure it meets your desires. Options include:
- Standing Stones of Stenness
- The Ring of Brodgar
- Barnhouse Village
- Ness of Brodgar
- Maeshowe
- Skara Brea and much more
Overnight: Kirkwall | The Foveran Hotel
Room Type: 1x Double Room - Kingsize
Meals Included: Breakfast
Day 12 - Thursday 25th September - Return to Mainland
Today you return to mainland Scotland, bidding farewell to Orkney and your time there. You will dock back into Scrabster, before taking the drive along the north east coast towards Inverness. Arrive at your accommodation in the capital of the highlands and enjoy some time relaxing or exploring the city.
Overnight: Inverness | Lochardil House Hotel
Room Type: 1x Deluxe King Room
Meals Included: Breakfast
Day 13 - Friday 26th September - The Capital of Scotland
After a leisurely breakfast it is time to head south towards the capital of Scotland, Edinburgh. On route there are lots of great stops for a leg stretch and some lunch. The charming town of Aviemore in the Cairngorms is one option with lots of good cafes, or the highland Perthshire town of Pitlochry is another great location.
Upon arrival into Edinburgh, return your hire car and make your way to your city centre hotel and some well earned down time.
Overnight: Edinburgh | Kimpton Charlotte Square
Room Type: 1x King Premium
Meals Included: Breakfast
Day 14 - Saturday 27th September - Exploring Edinburgh
This morning immerse yourselves in the winding cobbled streets of historic Old Town Edinburgh as you enjoy a private walking tour with an expert local guide. Discover the highlights of this unique capital city from the Palace of Holyroodhouse all the way up the ‘Royal Mile’ to the mighty ancient fortress which is Edinburgh Castle itself. Walk the ramparts atop castle rock and hear the tales of the One O’Clock gun and the stories of locals of times past. Your guide will leave you here so that you can spend as much time in the castle as you wish.
You then have a free afternoon to continue explorations at your own pace, pick up souvenirs or relax as you prefer.
Overnight: Edinburgh | Kimpton Charlotte Square
Room Type: 1x King Premium
Meals Included: Breakfast
Day 15 - Sunday 28th September - Depart
A private transfer will collect you from your accommodation and take you to the airport to make your onward connections. Waving farewell for now but taking with you special memories and wonderful stories of your explorations.
Meals Included: Breakfast
Trip Details
- Inclusions
- 14 nights accommodation, as stated in the itinerary above
- Most meals, as stated in the itinerary above
- Rental car hire from day 4 to day 13
- Private Airport Transfer on Arrival Day, includes Meet & Greet
- Private Airport Transfer on Departure Day
- All Ferry Travel Included in the Itinerary
- All guided hikes mentioned in the itinerary
- Entrance fees and activities mentioned in the itinerary, specifically:
- Day 2 – A private half day walking tour of Glasgow with a local city guide
- Day 3 – A guide food tour of Glasgow
- Day 5 – A private boat tour departing from Oban
- Day 7 – A private full day tour of the Isle of Skye with a local expert
- Day 10 – An Island wool experience – learning about the processes
- Day 11 – A tour around Orkney and some of its historical sites
- Day 14 – A private half day walking tour of Edinburgh with a local city guide
- Day 14 – Entry into Edinburgh Castle
- Personalised trip design and delivery
- 24/7 In-Country Support from the Wilderness Team
- Exclusions
- Flights
- Travel insurance
- Meals not mentioned in the inclusions
- Activities and entrance fees not mentioned in the inclusions
- Gratuities for the main driver guide
- Notes
- All suggested accommodations and services are subject to availability at the time of booking.
- A 20% deposit is required before any accommodation and services will be confirmed.
- This quote is valid for 14 days from the date quoted, after this time pricing may be subject to revision.
- Activities are only private if so specified.
- Pricing
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The NET price for this itinerary, based on 2 clients on a twin-share basis, and including a £12 per person conservation contribution is:
- £8,495 GBP per person
Conservation Contribution This voluntary donation of £12 per person goes towards conservation projects in the locations in which we operate. If you would like to opt out, just let your trip designer know. Click here for more information.
- Terms & Conditions
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Please see our booking terms here.
A Drive Through Scotland
Sunday 14th September – Sunday 28th September 2025