From Oxford to the Highlands

The Willis Family

Sunday 19th May – Sunday 26th May 2024

Number of Travellers: 4
Duration: 8 Days / 7 Nights


On a carefully crafted, bespoke trip, explore the pastoral beauty of England and the rugged wilderness of Scotland. From Oxford, travel north through the rolling hills of the Yorkshire Dales National Park. Meet locals and enjoy a traditional sheepdog demonstration before heading back to the past with a visit to Hadrian’s Wall. Travel to Scotland and spend time in St Andrews before making your way to the salt-stung, seaweed-strewn shores of the West Coast. Take a boat trip to Iona and discover the ancient history of Kilmartin Glen. Bring your trip to a close surrounded by the stunning architecture of Edinburgh, enjoying a spooky tour through its subterranean streets. On an adventure designed just for you, immerse yourself in the history, heritage and distinctive springtime beauty of the Highlands.


  • Visit the Isle of Eriska and enjoy a private boat trip to Iona.
  • Explore the spectacular Glencoe Glen on a fully-guided hiking adventure.
  • Discover the gruesome history and tall tales of Edinburgh's shadowy underground streets.

Day by Day

Day 1 - Sunday 19th May - Arrive in the Yorkshire Dales

This morning, pick up your car hire and travel north to the Yorkshire Dales. Nestled amidst a patchwork of rolling hills and meandering streams, the Yorkshire Dales National Park unveils a tapestry of rugged beauty. Cascading waterfalls, limestone crags, and ancient valleys crisscrossed with stone dyke walls and dotted with hardy sheep. Admire the beautiful scenery as you settle into your boutique country house hotel, which is nestled in the hills outside of the market town of Hawes. Enjoy a stroll around the town before enjoying dinner and a good night’s sleep.

Overnight: Hawes | Stone House Hotel
Meals Included: None

Day 2 - Monday 20th May - Sheep Dogs, History and into Scotland

After breakfast this morning, head out to meet a local shepherd for a sheepdog demonstration. You’ll watch as these amazing dogs work together with each other and the farmer to herd their flock of sheep expertly. A quick stop in Hawes to visit the Wensleydale Creamery you’ll be on your way north. Before crossing the border, stop at Vindolanda, an excavated Roman fort and village along the UNESCO World Heritage site of Hadrian’s Wall. Visit the award-winning museums to learn the history as well as the archaeological work that is still ongoing. Later, cross into Scotland, skirt Edinburgh and head to St Andrews, where you’ll stay with your friends.

Overnight: St Andrews
Meals Included: Breakfast

Day 2 - Sheepdog Demonstration Read More +

Activity: Sheepdog Demonstration
Richard Fawcett:
Start Location: Yorkshire Dales | Start Time: 9:30 am | Approx Duration: 1.5 hrs

Phone: +44 (0) 7593 966271

Leave your car at the hotel and walk a short distance down Brunt Acres Road. The farmer is Richard Fawcett whose field is on the right as you walk down Brunt Acres Road. The field is accessible by a metal gate. Please wear suitable footwear as it may be muddy.

Day 2 - Visit to Roman Fort Read More +

Activity: Visit to Roman Fort
Start Location: Vindolanda | Start Time: 2:00 pm | Approx Duration: 1.5 hrs

Booking Reference: BLA-COL-DQPCRB-H
Phone: +44 (0) 1434 344 277 | Website:

Please quote your booking reference number and Wilderness Scotland.
Chesterholm Museum
Bardon Mill,
NE47 7JN

Day 3 - Tuesday 21st May - Explore St Andrews

After breakfast, set out to explore St Andrews. Visit old stomping grounds, perhaps visit the town, enjoy coastal walks to pretty fishing villages or check out Dunino Denm to look for fairies. The day is yours to spend how you wish.

Overnight: St Andrews
Meals Included: None

Day 4 - Wednesday 22nd May - Highland Estate Tour & Travel West

This morning, you’ll travel to the west coast. Along the way, you’ll stop at the Highland Estate of Straloch. Here, you’ll meet the estate owners, giving you a glimpse into Highland life. Once on the estate try your hand at fly fishing in the estate loch or wander round the gardens and meet the rescue donkeys. Then jump in the Landrover to travel into the hills where you will enjoy lunch with a view. Later, continue west; arriving at your hotel, there may be time to wander around the grounds or even make use of the spa before dinner.


Overnight: Benderloch | Isle of Eriska
Meals Included: Lunch

Day 4 - Wild Picnic and Fishing on the Loch Read More +

Activity: Wild Picnic and Fishing on the Loch
Estate Owner: Will Holt
Start Location: Straloch Estate | Start Time: 10:30 am | Approx Duration: 4 hrs

Phone: +44 (0)7941 152 049

Please meet Will at:

Straloch Estate
PH10 7PH

Day 4 - Dinner Details Read More +

Restaurant: Isle of Eriska Hotel | Location: Benderloch
Reservation Time: 7:00 pm
Phone: +44 (0)1631 720 371 | Website:

Please pay locally

Day 5 - Thursday 23rd May - Hiking in Glencoe

After breakfast, wind your way to Glencoe for a wonderful day of guided hiking. This spectacular glen – carved out centuries ago by glaciers and volcanic eruptions – is full of harrowing history, fascinating geology and commanding views. With many excellent walks to choose from, chat with your guide and settle upon a route perfectly suited to you. One great option is to hike along a narrow, rowan-hung gorge until you reach the Lost Valley. This enclosed meadow, high, green and hidden by precipitous tors, is said to be where the Macdonald Clan used to conceal their rustled cattle. After your hike, head to a local hiker’s inn for dinner, and hopefully, you will catch some live music.

Overnight: Benderloch | Isle of Eriska
Meals Included: Breakfast and Lunch

Day 5 - Dinner Details Read More +

Restaurant: Clachaig Inn | Location: Glencoe
Phone: +44 (0) 1855 811 252 | Website:

Table reservations are not possible but if you aim to be there at around 6pm you should get a table. Please pay locally.

Day 5 - Guide Details - Ray Allwood Read More +

Name: Ray Allwood
Contact Number: +44 (0) 7740 920 059
Meeting Place: Glencoe Visitor Center Car Park | Meeting Time: 9:30 am

Ray will meet you in the car park of the Glencoe Center next to the entrance.

Day 6 - Friday 24th May - Boat Trip and Iona Visit

Today, join an experienced, well-seasoned skipper for a private boat trip. From the Isle of Eriska, zoom out onto the smooth water to keep an eye out for wildlife that make this wild part of Scotland. Head out to Iona and spend time on shore exploring and visiting the Nunnery and Abbey. On your return journey, visit the remarkable Eileach an Naoimh or Isle of the Saints. There is no public ferry, so these islands are rarely visited, and the unusual beehive remains of the monastery established by St Brendan around AD 542 are well preserved. Take time to explore the islands before heading back to your castle hotel.


Overnight: Benderloch | Isle of Eriska
Meals Included: Breakfast

Day 6 - Private Boat Trip Read More +

Activity: Private Boat Trip

Start Location: Isle of Eriska Jetty | Start Time: 10:00 am | Approx Duration: 6 hrs

Phone: +44 (0) 1631 565 833

Please meet the boat at the Isle of Eriska Jetty, the hotel will point you in the right direction!


Day 6 - Dinner Details Read More +

Hotel: Isle of Eriska Hotel | Location: Benderloch
Reservation Time: 7:00 pm
Phone: +44 (0) 1631 720 371 | Website:

Please pay locally

Day 7 - Saturday 25th May - Kilmartin Glen & Travel to Edinburgh

As red deer graze quietly across the heathery hillsides, enjoy breakfast before travelling down the west coast towards Edinburgh. Along the way, stop to explore Kilmartin Glen, a place where human history can be traced back over 5000 years. Visit the newly renovated museum and then head out to walk among the stone circles, burial chambers and standing stones. Back in the architecturally stunning city of Edinburgh, enjoy a tour of the city’s catacombs, exploring the underground vaults and winding streets where dark secrets lurk in the crumbling shadows. With many fantastic restaurants to choose from tonight, head out to enjoy a delicious, celebratory dinner to bring your Scottish adventure to its perfect close.

Overnight: Edinburgh | Kimpton Charlotte Square
Meals Included: Breakfast

Day 7 - Kilmartin Glen Visit Read More +

Activity: Kilmartin Glen Visit
Start Location: Kilmartin Glen | Approx Duration: 2.5 hrs


This is an optional extra but well worth the visit. Please pay locally for entry to the museum.

Day 7 - Real Mary King's Close Tour Read More +

Activity: Real Mary King's Close Tour
Start Location: Royal Mile, Edinburgh | Start Time: 5:15 pm | Approx Duration: 1 hrs

Booking Reference: 41771188
Phone: +44 (0) 131 225 0672 | Website:

Please arrive 10 minutes before and quote the reference number and Wilderness Scotland. This is a Flexi Ticket and the start time can be altered up to 6 hours before.
The Real Mary King’s Close
2 Warriston’s Cl

Day 8 - Sunday 26th May - Depart for Home

Depending on your departure time today, enjoy a relaxed breakfast and perhaps a stroll around some of Edinburgh’s cobbled streets before catching the tram or a taxi to the airport to begin your journey home.

Meals Included: Breakfast

Trip Details

Inclusions Read More
  • All accommodation from Day 1 to Day 8
  • Meals as indicated above
  • Services of an experienced and knowledgeable qualified guide on Day 5
  • All guided hikes and activities mentioned in the itinerary including:
    • Sheep dog demo
    • Vindolanda entry
    • Fly-fishing and Highland Estate picnic
    • Guided hiking in Glencoe
    • Private full day chartered boat trip
    • Mary King’s Close Tour
  • Personalised trip design and delivery
  • 24 hour in-country support from the Wilderness Team
Exclusions Read More
  • Flights
  • Travel insurance
  • Meals not mentioned in the inclusions
  • Transport to and from car hire pick up or to the airport
  • Activities and entrance fees not mentioned in the inclusions
  • Gratuities

Get in Touch


Stone House Hotel

Sedbusk | Hawes | North Yorkshire |
DL8 3PT | England
Phone: +44 (0) 1969 667 571

Isle of Eriska

Benderloch | Argyll |
PA37 1SD | Scotland
Phone: +44 (0)1631 720 371

Kimpton Charlotte Square

38 Charlotte Square | Edinburgh | Midlothian |
EH2 4HQ | Scotland
Phone: 800 44445 566

Meet Your Guide

Ray Allwood

Contact Number: +44 (0) 7740 920 059

I’m a keen hiker, cyclist, climber, mountaineer and skier, not necessarily in that order.

My interest in the outdoors started in 1989 when as a BT apprentice I was sent on an outward bounds course. We spent a week walking, climbing and camping in Purbeck, Dorset. This led me to join a Mountaineering club and a joy of climbing and hiking started, ultimately leading to my qualifications as an Outdoor Professional.

Full Web Bio