Self-Drive - Isle of Skye

Lia, Jef, Lynn, Gert Jan, Christian, Joost, Jan & Michelle

Monday 12th May – Friday 16th May 2025

Number of Travellers: 8
Duration: 5 Days / 4 Nights

Overview

Immortalised in stories and songs, the Isle of Skye has long attracted travellers to its wild shores. The dramatic mountains, rugged coastline and rich history full of myth and legend make it the perfect place to escape and reconnect with the natural environment. This enriching self-driving short break includes a mix of self guided exploration and guided activities led by a local expert, allowing you to get to know Scotland’s most famous island.

From a central base on the island, you’ll set out each day to explore, walking through history and spectacular scenery with your guide. You will visit a coastal crofting village abandoned during the turbulent Highland Clearances and take a boat trip into the heart of the Black Cuillin to a wild and remote loch. Enjoy the warm and welcoming hospitality the Highlands are famous for and fresh local produce from the land and sea around the island.

Itinerary at a Glance

Day 1 | Monday 12th May | Over the Sea to Skye | Overnight: Portree

Day 2 | Tuesday 13th May | The Clearance Villages | Overnight: Portree

Day 3 | Wednesday 14th May | Loch Coruisk & The Black Cuillin | Overnight: Portree

Day 4 | Thursday 15th May | Free Day to Explore | Overnight: Portree

Day 5 | Friday 16th May | Exploring Portree & Departure

Day by Day

Day 1 - Monday 12th May - Over the Sea to Skye

Your journey starts by heading west toward Scotland’s most famous island. As you travel through the Highlands enjoy incredible scenery and pass famous landmarks. You could visit the iconic Eilean Donan Castle, situated on a private island at the confluence of three sea lochs. It is undoubtedly one of the most picturesque castles in Scotland. After crossing the Skye Bridge, you’ll make your way to your accommodation, arriving in time to settle in and relax before heading out to enjoy some dinner.

Overnight: Portree | Rosedale Hotel
Meals Included: None

Day 2 - Tuesday 13th May - The Clearance Villages

Today, you’ll meet your Wilderness Scotland guide, Will, and explore Skye’s breathtaking scenery. The hikes will be individually tailored, considering your experience, interests and the weather. One poignant option is a coastal circuit that passes through the ruins of two crofting villages which were abandoned during the Highland Clearances. Will can share the stories of the area and help you picture what life was like for the crofters who lived and worked on this land. Whatever option you choose, keep an eye out for wildlife. Skye is home to Scotland’s largest population of white-tailed sea eagles.

Overnight: Portree | Rosedale Hotel
Meals Included: Breakfast

Day 2 - Guide Details - Will Hall Read More +

Name: Will Hall
Contact Number: +44(0)7725 467 739
Meeting Place: Rosedale Hotel | Meeting Time: 09:30

Meet Will at the Rosedale Hotel in Portree and chat through some options for the day. From here, jump in your vehicles and convoy to the start point of your walk. Please make sure to bring a packed lunch with you. These can be provided by your accommodation if notified the night before they are needed. Alternatively, you may wish to pick something up locally in Portree to take with you.

Day 3 - Wednesday 14th May - Loch Coruisk & The Black Cuillin

With a sharp amphitheatre of summits rising straight from the shoreline above mysterious deep grey waters, Loch Coruisk deserves its reputation as Scotland’s most dramatic loch. You’ll travel with Will today at a tiny harbour before crossing Loch Scavaig to the remote southern edge of the Cuillin. There is an excellent chance to spot wildlife, including porpoises and dolphins, as well as the seal colonies that occupy the skerries at the mouth of the loch. Once dropped off in this lonely and wild spot, you can choose to circumnavigate the loch, navigating through the erratic boulders left behind by glaciers, or, for a more challenging option, hike up a nearby peak for some of the most incredible views on Skye.

Overnight: Portree | Rosedale Hotel
Meals Included: Breakfast

Day 3 - Guide Details - Will Hall Read More +

Name: Will Hall
Contact Number: +44(0)7725 467 739
Meeting Place: Rosedale Hotel | Meeting Time: 09:30

Meet Will at the Rosedale Hotel in Portree and chat through some options for the day. From here, jump in your vehicles and convoy to the start point of your walk. Please make sure to bring a packed lunch with you. These can be provided by your accommodation if notified the night before they are needed. Alternatively, you may wish to pick something up locally in Portree to take with you.

Day 4 - Thursday 15th May - Free Day to Explore

A free day for you to explore at your own pace. The Quiraing is one of Skye’s most fascinating landscapes. Several walking routes bear testament to the island’s unique geology, or visit one of the other natural features for which Skye is so rightly famous, including the Old Man of Storr and the very popular Fairy Pools. Or, perhaps head to the island’s northwest and visit the impressive Dunvegan Castle and gardens.

Overnight: Portree | Rosedale Hotel
Meals Included: Breakfast

Day 5 - Friday 16th May - Exploring Portree & Departure

After a relaxing breakfast, spend time this morning exploring Portree. The largest town on Skye boasts quirky wee shops and galleries and a busy, colourful harbour. After a spot of lunch, head for home or continue your adventure in the Highland wherever it leads you.

Meals Included: Breakfast

Trip Details

Inclusions Read More
  • Four nights accommodation
  • Meals as stated in the itinerary
  • 2 days of privately guided hikes led by an expert Wilderness Scotland guide
  • Boat trip to Loch Coruisk
  • Personalised trip design and delivery
  • Detailed trip itinerary and map
  • Pre-trip care and 24-hour in-country support from the Wilderness team
Exclusions Read More
  • Flights
  • Travel insurance
  • Meals not mentioned in the inclusions
  • Activities and entrance fees not mentioned in the inclusions
  • Gratuities for the main guide
Notes Read More
  • All suggested accommodations and services are subject to availability at the time of booking.
  • A 25% 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.
Important Contact Numbers Read More
Wilderness Scotland Office | 9:00am – 5:30pm

UK: +44 (0)1479 420 020
US: 888 351 5707

Out of Office Hours | 5:30pm – 9:00am

+44 (0)7766 794 640

Emergency Services

999

Important Additional Information Read More
Terms & Conditions Read More

Please see our booking terms here.

Get in Touch

Tel: 888 351 5707

Email Chris

Accommodation

Rosedale Hotel

Beaumont Crescent | Portree | Isle of Skye |
IV51 9DF | Phone: +44(0)1478 613 131
Web: rosedalehotelskye.co.uk

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Meet Your Guide

Will Hall

Contact Number: +44(0)7725 467 739

I’m an experienced wildlife guide and outdoor instructor based in Scotland, with a passion for helping people connect with nature. As a Mountain Leader and bushcraft instructor, I’ve guided countless adventures across Scotland’s stunning landscapes, from the rugged Cairngorms to the coasts of Moray and Inverness. My work has also taken me far beyond Scotland. I’ve led trips in some of the world’s most biodiverse regions, including the jungles of Borneo, Java and Costa Rica. These experiences have given me a deep appreciation for the interconnectedness of ecosystems and the importance of conserving wild places.

Full Web Bio

Virtuoso

Self-Drive – Isle of Skye

Monday 12th May – Friday 16th May 2025