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Selected Trips


    Selected Trips

      Road Cycling
      Outer Hebrides

      136 review(s)

      Next Trip(s): 25th Apr | 30th May Duration: 6 night(s)

      From £1,795 View Prices & Departures

      Trip Details & Highlights

      Trip created by Paul Easto
      View Paul's Profile

      Region: Outer Hebrides and St Kilda
      Trip Type: Road Cycling
      Comfort: Classic
      Confirmed: When 2 Traveller(s) Book
      Deposit From £448.75


      All you need to know about your trip, this essential document is a must for all adventures.

      Download Itinerary

      Trip Details

      This amazing cycling trip in the Outer Hebrides takes you through some of the most beautiful and unspoiled regions of Scotland, journeying past spectacular white sand beaches, rugged mountains and wild glens. In the Outer Hebrides, you will find the Gaelic language is still spoken and the rich history and culture is embraced.

      You will visit impressive ancient sites such as Callanish standing stones and the seat of the Clan Macneil. Stay in a range of 4 star accommodations from an intimate boutique hotel to a cosy guesthouse including a converted house: a place where one could wait for the ferry, the original building dates back to circa 1750 and retains many of its original features.

      Need a bike? See our bike hire page for details.

      Trip Highlights

      • Cycle tour from Barra to Lewis through nine amazing islands of the Outer Hebrides.
      • Admire the outstanding landscapes of white sand beaches and towering shapely peaks.
      • Enjoy the fascinating history, rich culture and warm hospitality of the islands.

      Day by Day Itinerary

      Day 1 – Inverness to South Uist

      We meet in Inverness in the morning and drive west through the Highlands. Our adventure really begins as we cross first to the Isle of Skye from where we board the ferry from Uig. We’ll keep our eyes peeled for whales and marine wildlife on the crossing, before winding our way through a scattering of skerries to alight at Lochmaddy, our first landfall on the wonderful Outer Hebrides. From here we transfer south across the islands of North and South Uist to our accommodation on the southern shore of the island where we enjoy a welcome dinner. (D)

      Day 2 – Barra and Eriskay

      This morning we will ride from the hotel to the small island of Erisaky where Bonnie Prince Charlie and ‘the Seven Men of Moidart’ landed in 1745 to begin the Jacobite Rising. Here we board the ferry to Barra, where we’ll have the opportunity to watch the planes land on the beach, visit some old churchyards, and ride a loop of the island, taking in Kisimul Castle – ‘The Castle in the Sea’ at Castlebay. Continuing up the west coast we get glorious views of the Atlantic. Later this afternoon we take the ferry back across the Sound of Barra to the Isle of Eriskay and enjoy a drink at the Am Politician pub. (B, L)
      Distance: 59 km/ 37 miles, Ascent 400m/ 1,310 ft

      Day 3 – South Uist, Benbecula and North Uist

      We begin Day 3 at an ancient standing stone outside the inn and head north, following the west coast with the the wild machair either side of us. The machair is a fertile habitat supporting an amazing amount of wild flowers in spring and summer. It is at its most extensive in the Outer Hebrides, and combines beautifully with brilliant white beaches, gentle dunes and expanses of fresh-water lochans where a host of bird species thrive including buntings. The terrain also makes for very flat cycling and with the prevailing wind easing our way north we cross the tiny island of Benbecula and continue onto North Uist. (B, L)

      Distance: 75 km/ 48 miles, Ascent 365m/ 1200 ft

      Day 4 – North Uist to Harris

      This morning is a time to savour the flat terrain of the Uists as we head NE, and then beyond, crossing the causeway to Berneray. From here we cross the beautiful Sound of Harris – surely one of the best wee ferries in the world! As soon as you land on the Island of Harris, you will be struck by the more mountainous landscape where ancient peaks rise right out of the sea. Our ride north follows the coast past some truly amazing beaches. A stop off at one of the island’s excellent cafes and art gallery is a must and fuels us for the final part of the day to the island’s “capital” of Tarbert. Here we stay in an excellent 4* Hotel right by the harbour. (B, L)

      Distance: 59 km/ 36 miles, Ascent 640m/ 2100 ft

      Day 5 – Harris to the Isle of Lewis

      Following breakfast, we will visit the local Harris Tweed weavers – to see the island’s world famous export first hand. From Tarbert, our journey continues north – this being our most challenging day as we climb through the hills of North Harris. The scenery more than makes up for the effort as we traverse beneath the striking mountain of An Clisham – the highest point on the Outer Hebrides. Keep an eye out for Golden Eagles here. Crossing the spectacular fjord of Loch Seaforth, we continue onto the Isle of Lewis and across the wild moor before turning west back to the coast. Our destination for today is the mysterious Callanish standing stones; dating back over 5000 years this ancient site provides a fitting end to a memorable day of riding. For the next two nights, our home is a friendly 4* Guest House a short distance from the stones. (B, L)

      Distance: 64 km/ 38 miles, Ascent 660m/ 2160 ft

      Day 6 – Callanish to the Butt of Lewis

      Our final day follows the west coast of Lewis and is full of historical and cultural interest. Heading north, we soon pass the ancient Dun Carloway Broch and then the Blackhouse Village at Gearrannan which offers an insight into what island living was like not so many years ago. An impossible to miss feature on our final push is the Whalebone Arch, recovered from a huge whale washed up on a beach nearby. A turning of the road to the west signals the last few miles. Perched on the Atlantic at the very edge of Europe, the Butt of Lewis is a spectacular and fitting place to end our trip through the Hebrides. After celebratory drinks, we head back to our accommodation at Callanish for our final night on the islands. (B, L, D)

      Distance: 56 km/ 34 miles, Ascent 490m/ 1600 ft

      Day 7 – Return to Inverness

      On our final morning we have the option to do one last ride – crossing the Isle of Lewis to arrive in the island capital of Stornoway. Or we can ride in the van if we feel our legs have done enough! in Stornoway we can visit the freshly renovated Lews Castle with its museum and restaurant.

      Following lunch we will board the ferry for the scenic journey back to Ullapool on the mainland. From Ullapool it is approximately 1.5 hour’s drive to Inverness where we will arrive around 6.30pm. (B)

      Download Detailed Itinerary

      Road Cycling
      Outer Hebrides

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      What's Included

      Accommodation - Accommodation in carefully selected guest houses and hotels Read More

      This trip features some of the best hotel and guest house accommodation and food along the route we travel. We use a variety of accommodations such as country inns, guesthouses and small hotels, all hand-picked by us. Accommodation is in a choice of double or twin rooms with ensuite facilities.

      There is no supplement charged to solo travellers, however you will be required to share a room with another person of the same sex. If you require a single room please request this at the time of booking and we will check availability for you. A single room supplement of £350 is charged if a single room is available

      Meals - Meals Info (B=Breakfast, L=Lunch, D=Dinner) Read More

      Lunch each day will be either a wilderness picnic or taken at a local cafe/restaurant. Drinks and snacks are provided throughout the day as you require. Evening meals are included on the first and final evenings, and on this itinerary and we have the flexibility to take evening meals in local restaurants or pubs. Based upon our knowledge and experience, we will visit the best places to eat along the route.

      On this trip we generally eat dinner as a group however if you would like to make alternative arrangements you are free to do so. Your guide will have an evening off during this trip where they do not eat with the group. They will recommend options for dinner that evening and will help you make any necessary reservations.

      Travel - All transport throughout the trip Read More

      You will be met by your Wilderness Scotland Guide at Inverness Railway Station at 9:00am on Day 1 of your trip. You will be returned to Inverness Station for 7:00pm on the final day.

      For advice on getting to and from Scotland please our travel advice page on our website:

      Trip Dates & Prices

      Trip Dates for 2020 Availability Status Price Book
      25th Apr - 1st May 2020 1 place(s) left CONFIRMED £1,795 Book Now
      30th May - 5th Jun 2020 Trip Full FULLY BOOKED £1,795
      4th Jul - 10th Jul 2020 6 place(s) left CONFIRMED £1,795 Book Now
      1st Aug - 7th Aug 2020 8 place(s) left UNCONFIRMED £1,795 Book Now
      22nd Aug - 28th Aug 2020 4 place(s) left CONFIRMED £1,795 Book Now
      5th Sep - 11th Sep 2020 Female only date 8 place(s) left UNCONFIRMED £1,795 Book Now

      Make This Trip Private

      Sometimes it's nice to get family and friends together and travel privately for some quality time. This means you benefit from all the features of the group departure, including hand-picked accommodation and expert local guides and we'll take care of it all. Then you can make your choice of departures dates and we'll get back to you to finalise the details.

      Speak to an Expert

      As founder of Wilderness Scotland Paul’s craving for adventure and knowledge of Scotland knows no bounds. His leadership has resulted in Wilderness Scotland twice being named as Best Green Tour Operator in the World at the World Travel Awards and ranked as No.1 Adventure Travel Company in Europe by National Geographic. Paul’s commitment to excellence in all that he pursues becomes obvious in the routes we follow and the little touches included in this trip.

      - Paul Easto

      Ask Paul a Question

      Meet Your Guide

      Difficulty Grades Explained

      Blue Graded Road Cycling Holidays 4-6

      Blue graded trips are suitable for people with a good level of bike fitness, who regularly enjoy cycling and may have joined a multi-day cycle holiday before.

      Distances each day will be between 35 – 45 miles, cycling at around 12/13mph. Each day will be rolling and hilly terrain and there will be notable climbs most days. Some of these will be more testing and some riders may opt to push or ride in the support vehicle. Some climbs are also followed by exciting descents. We will be in the saddle for 5 – 7 hours each day plus the odd longer day. There is also time each day for breaks and lunches, plus some visits to sites of interest.

      Compare road cycling grades

      Trip Reviews

      Rated 4.94 out of 5 based on 136 review(s) of Road Cycling – Outer Hebrides


      Every client receives a feedback survey when they return from their guided, self guided or tailor made holiday with us. Once completed the review is published on our website just as soon as our database updates. The little touches and details are important to us and where issues are raised we make positive changes to our trips to improve your experience.

      That’s why we read each of our client’s reviews and although we don’t respond to all of them, if it’s glowing feedback then we get the satisfaction of helping to make your holidays truly memorable.


      Harry Richardson

      Reviewed on 17/09/2019

      Age: 70 - 80
      Country: United Kingdom
      Trip Date: 31/08/2019
      Trips Taken: 1

      The Bottom Line

      The Bottom Line

      Excellent trip and an experience I will never forget...the E-bike also helped with the hills!


      Catherine Richardson

      Reviewed on 09/09/2019

      Age: 60 - 70
      Country: United Kingdom
      Trip Date: 31/08/2019
      Trips Taken: 1

      The Bottom Line

      The Bottom Line

      Despite the challenging weather at times, trip very enjoyable and fun. Good to see life on the Western Isles and cycle the Hebridean Way. Great group and excellent guides - nothing too much trouble for them. Great experience from booking to end of trip.


      Judy Goodall

      Reviewed on 09/09/2019

      Age: 60 - 70
      Country: United Kingdom
      Trip Date: 31/08/2019
      Trips Taken: 1

      The Bottom Line

      The Bottom Line

      Very well organised and well supported trip

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