Top Ten Best Cycling Challenges in the UK

Tour Overview.

The Hebridean Way twists and turns across ten islands of the Outer Hebrides. You’ll cross between them on causeways and ferries. The route is recognised by Lonely Planet as one of the ‘Epic Rides of the World’ and we at Cycle Britain agree!  We organise different tour options from fully guided tours with premimum accommdation to self-guided tours with baggage transfer.

To cycle in the Hebrides is to return to a quieter pace of life. You’ll pedal along lonely roads past white beaches and sunsets that melt into the turquoise sea, past lofty 800-metre mountains and through fertile grassy plains – or machairs to give the Gaelic word for one of Europe’s rarest habitats.

Each island is unique but together they form the beautiful mosaic of the Outer Hebrides. This wild archipelago, constantly buffeted by the Atlantic Ocean, supports a hardy collection of flowers, wildlife, birdlife and human-life! This trip squeezes 240 miles cycling, four ferries, ten islands, and a whole lot of adventure into just seven days!  Whether you would like to join the premium guided tour or the  standard accommdation tour we have it all planned so you can enjoy cycling and the amazing scenary.

Cycle Britain

256 miles / 7 Days

The fully supported, guided tours remove the hassle so all you have to focus on is the riding. Allow our guides to lead the way and teach you tips and tricks that will improve your cycling ability. Let our support vehicles carry your bags, resolve any mechanicals, and replenish your energy with feed stations and drinks.  For supported and guided tours we stay in accommodation which guarantees rest, delicious food and splendid views.

For cyclists looking for fully supported independent cycling experiences, Cycle Britain offers a fully supported tour. Our support vehicles carry your bags, assist any mechanicals, and support you fully and are never far away.  We monitor your progress and ensure you arrive safely.

For the cyclist that wants just baggage transfer, we provide the route and accommodation.  This fully independent option has us in reserve just in case you need further support.  The Hebrides tour is unique as it also has the option to do wild supported bike packing.

Our fully guided supported tours ride in a maximum group size of 12 and enjoy the support of our expert team of guides, support staff and drivers who’ll carry your bags, distribute snacks, help with repairs and lead you along the route while sharing stories that bring each day’s riding to life.


Tour Highlights.

  • Visit ten wild and diverse Hebridean islands!
  • Four picturesque ferry journeys (all included in the price)!
  • The rugged landscapes of the Hebrides; white beaches of crushed shells, 800-metre peaks, fertile lowland plains or machairs.
  • The Golden Road to Tarbert.
  • Reaching the Butt of Lewis lighthouse.
  • The satisfaction of riding the Hebridean Way, one of Lonely Planet’s Epic Rides of the World.
  • Making new friends and enjoying the camaraderie of riding in a group of 12.
  • Evening meal in each hotel included from the menu. Please note up to £25 for food included. (Alcohol not included)
  • Low-traffic roads perfect for peaceful cycling.
  • Calanais Standing Stones. Nearly 50 megaliths which date from around 3000 BC.

Summary of the Tour.

  1. Oban to Barra (8 miles)

    After a group meeting giving us a chance to get to know each other and discuss the trip, we enjoy an exploratory loop of Oban. At 1:30 pm we board the ferry for the Outer Hebrides. The five-hour crossing reveals beautiful coastal panoramas before sailing into Castlebay, so-named because of Kisimul Castle guarding the bay. Since 2001, the castle has been rented to Historic Scotland on a 1,000-year lease for the annual price of £1 and a bottle of whisky.

  2. Barra Loop (27 miles)

    One important stop on today’s loop ride is the southern tip of Vatersay. This is the southernmost peninsular of the Hebridean Archipelago and the official start of the Hebridean Way. The lap of Barra (Barradise) takes you on singletrack roads, past pristine white beaches and shimmering coves with enticing names such as Seal Bay. Traigh Mhor beach forms one of Britain’s most interesting airports as the sandy shore becomes a runway for the island.

  3. Barra to North Uist (69 miles)

    Today’s cycling adventure takes in six islands: Barra, Eriksay, South Uist, Benbecula, Grimsay, and North Uist. Water provides constant companionship throughout. In the morning, a ferry sails us across the dazzling sound from Barra to Eriksay, a journey lasting forty minutes. The remaining islands are linked by a necklace of causeways and navigable by bike. These islands are flat and punctuated by lochs and lochans. We stay at the Lochmaddy Hotel, whose 150-year history has placed it well to offer the best hospitality on North Uist.

  4. North Uist to Tarbert (53 miles)

    Continue cycling along the west coast of North Uist on desolate singletrack roads. You’ll briefly land on Berneray Island before boarding the ferry for the island of Harris. Once on Harris, you’ll pedal along the west coast, which enjoys some of Britain’s most spectacular beaches, before crossing to the east coast to ride ‘the Golden Road’. When the Golden Road was built in 1897, it was intended to connect a string of settlements previously only accessibly by sea. Little did its creators know they were designing a dreamy cycling route that passes isolated hamlets and spectacular scenery!

  5. Exploring Harris Beaches and Tarbert (50 miles)

    Staying on Harris for the day we embark on a wonderful day of cycling and exploration. Our expert team show you the hidden gems of Harris and visit some of the best beaches in the world. The support van team cook a spectacular lunch on our Indian Kadai before we return to the hotel for the evening.

  6. Tarbert to the Butt of Lewis (77 miles)

    North of Tarbert , Harris Island becomes less green and more rugged. The machairs are replaced by mountains, which are made from Lewisian Gneiss, some of the oldest rock found anywhere in the world - some 2.6 billion years old! The islands bear countless scars, in the form of lochs and lochans gouged by ancient glaciers. At the north of Lewis, waves crash against exposed rock under the stern gaze of a sentinel lighthouse. Congratulations, this is The Butt of Lewis and the end of the Hebridean Way. From here, we transfer to Stornoway for our celebratory final evening.

  7. Stornaway to Ullapool, Oban and home (0 miles)

    We finish the tour with the final ferry to Stornaway. At this point you can join us on the return travel home or continue your journey.


This cycle tour offers an exciting opportunity to visit ten different islands, each unique yet together forming a mosaic of the Outer Hebrides.

The adventure begins on the Scottish Mainland in Oban, known as the ‘Gateway to the Isles’. Stepping off the ferry in Barra after six hours of sailing, you will discover you have returned to a simpler time with a slower pace of life. As you will learn, things are different in the Hebrides.

Our journey begins from Vatersay which is the archipelago’s most southerly inhabited island. From here, we head north. The journey will pass white beaches lapped by turquoise waters that would appear more appropriate in the Tropics. You’ll ride through Machairs [fertile, low-lying grassy plains] and lochs and lochans that were engraved into the islands during the last Ice Age.

Keep your eyes peeled, and you might spot Eriskay Ponies, seals, or flocks of migratory birds that call these islands home throughout the summer.

The islands have a rich history. Some of it is ancient, such as the 5,000 years-old Calanais Standing Stones, and some of it is more recent, such as the 1897 poetically-named ‘Golden Road to Tarbert’, or the sinking of the S.S Politican, a cargo ship, in 1941.

Further north, the machairs give way to lofty 800-metre mountains and a rugged lunar landscape. These mountains are formed from Lewisian Gneiss, one of the world’s oldest rocks.

The Butt of Lewis forms a dramatic finish line to the adventure. Here, Atlantic waves crash against exposed rock under the stern gaze of a sentinel lighthouse. We celebrate in Stornoway with an evening banquet reminiscing the last week’s adventures, before returning to Oban the following morning.

Dates and Prices.

  • 23rd May -
    29th May 2022

    7 day tour with 6 nights premium accommodation. Based on single occupancy. Fully supported and guided tour with lunch, snacks, drinks and evening meals. (All ferries included)

  • 23rd May -
    29th May 2022

    7 day tour with 6 nights premium accommodation. Shared room with another guest or person of your choice.
    Fully supported and guided tour with lunch, snacks, drinks and evening meals. (All ferries included)


All our routes are available to our Komoot followers.  Follow Cycle Britain on Komoot.

What’s Included.

All transport

Four ferries and two vehicle transfers.

Celebratory final evening banquet in Stornoway.

We love to conclude our trips with a celebratory meal on the final evening.

Fully-supported tour

The Alex Wagon is the name of the Cycle Britain support vehicle. It is named after our amazing lead support manager, Alex. He's there to help with anything you may need and will track you on your journey to ensure you have the support required.

Nutritious breakfasts, lunches and snacks.

After a hearty breakfast, the Alex Wagon becomes a pop-up cafe providing nutritious lunches, snacks, and sports drinks throughout your ride.

Cycle Britain tour guide, komoot mapping & detailed route notes

We are an official partner with komoot and make your route available to you once you have booked so you can check the full details of the tour. We provide GPX and TCX files. These can be transferred onto Garmin and Wahoo. When you attend a tour you will receive all the route notes and our free guide as a PDF. Information is also provided in our navigation notes to read on arrival. With detailed trip notes, komoot mapping and your guide, you can't go far wrong.

Live tracking

Our live tracking allows you to share your journey.

Microsoft Teams Tour Groups

We use Microsoft Teams to help you get to know your team before your departure.

Free use of soft bike bag if needed

Storage bag for your bike if required to take it into your hotel.


6 nights accommodation in 3* and 4* hotels and inns. Unless requested otherwise, we book single rooms to ensure the best rest and recovery.

Expert staff

We are available to support your trip and answer any questions.

Route plans

Accessible as a GPS track on your phone before you even leave. All you need is your phone to use our turn-by-turn navigation.

Daily luggage transfer

We carry your bags between hotels so you don’t have to! When you arrive at the hotel your bags will be waiting in your room for you. We also manage your day-bag and ensure it’s available when you need something.

Unrivalled knowledge of cycling in Britain

We pride ourselves on being the experts on cycling in Britain.

Free guide to nutrition, training and bike setup

To help you prepare for this demanding tour, we provide you with free guides on what to eat, how to train and general bike setup tips.

Free Transfers to Oban.

As a special deal for our 19th Septembert 2021 departure, we are pleased to offer free door-to-door transport for any clients coming from the North of England.

What’s Not Included.

A bike and helmet

Please provide your own bike and helmet for this trip. Get in touch if you have any questions regarding whether your equipment is appropriate.

Travel Insurance

We highly recommend you take out insurance. We recommend the insurance covers loss due to COVID 19.

Post-tour accommodation in Oban

Many of our guests head home from Oban, but we are happy to arrange a hotel if you prefer to stay another night.

Evening Meals

We prefer to give you flexibility for your dinners. We do, however, include a celebratory banquet on your final evening.


We have chosen the best accommodation options available where we are sure you’ll find warm hospitality and enjoy a comfortable and memorable stay.  The pandemic has created a challenge but we have put together some amaxing tours.

For our September 2021  tour we have teamed up with the best hotels  in the area.    For the first time we are delighted to stay at the amaxing Isle of Barra Beach Hotel for the first two night.  .    We also enjoy two nights in the Borodale Hotel  and the final two nights in the Harris Hotel which a truly unique and fantastic hotel and enjoy dinner at 8pm in the dining room.

Trip Suitability.

This tour is suitable for everyone as you can cycle as much or as little of each day as you like.   We have a support vehicle to put your bike into and transport you once you have done enough.  Some of the days involve spending the day exploring and some days are longer for those that want a challenge.  Join us on this inclusive tour and epic journey.

This is a Grade 4 tour, which means it is suitable ‘for those that want a challenge.’ These routes ‘provide a challenge to complete climbs and steep descents’ and involve ’60 – 100 miles per day.’

Leading up to your trip, we would be glad to help with your training program;
– We hold regular Zwift sessions which are a great opportunity to get bike-fit and meet fellow cyclists. 
– We provide training weekends in the Peak District led by qualified coaches. 
– We can tailor a training plan to your fitness, requirements and schedule. 
For any of these training plans, check out our coaching packages or contact us. 

For a different challenge altogether, check out our popular North Coast 500 Road Tour or our LEJOG 9-day Road Tour.


Frequently Asked Questions.

Do you cater to vegan and vegetarian diets?

Absolutely! Inform us in advance of any dietary requirements and we will be glad to cater to you.

Will we be able to wash our clothes on the trip?

There will be opportunities to wash clothes and leaders can take your items to a launderette.

Can I charge my phone?

We have a charging station in the support van.

What level of fitness do I need?

This tour is suitable for everyone as you can cycle as much or as little of each day as you like. We have a support vehicle to put your bike into and transport you once you have done enough. Some of the days involve spending the day exploring and some days are longer for those that want a challenge. Join us on this inclusive tour and epic journey. Overall this is a Grade 4 tour, which means it is suitable for ‘for those that want a challenge.’ These routes ‘provide a challenge to complete climbs and steep descents’ and involve ’60 – 100 miles per day.’ Check out our coaching section for more info. The tour allows time to balance enjoyable days mixed with challenging days.

What level of ability do I need?

A moderate level ability and experience is required as we have full vehicle support.

What level of support is offered?

This trip has full vehicle support meaning everything you need is taken care of. We provide breakfasts, lunches and snacks and can offer advice on nutrition, equipment, preparation and training. We provide detailed route notes and GPX files.