Cycling The Scottish Isles Outer Hebrides & St Kilda

Description

One of our brand new trips for 2027 is a ten day stunning tour that takes in The Outer Hebrides and UNESCO world heritage site St Kilda, described as the island at the egde of the world. This truly is an authentic cycling experience not to be missed, delivered in association with our local cycling partner Bespoke Cycles (Stornoway) Ltd, providing local knowledge and cycling expertise with a back up van and bike mechanic and full support throughout the trip.

Our trip follows The Hebridean Way, a spectaculer 185 mile long distance route traversing 10 islands, 6 causeways, 2 ferries across the Outer Hebrides and much more besides. Running from Vatersay to the Butt of Lewis, it features dramatic beaches, rugged hills, Gaelic culture, and abundant wildlife. In total, our trip is about 257 miles including cycling around Barra.

The remote and spectacular Outer Hebrides have always been a lure to cyclists seeking out tranquil roads, stunning views and ancient history. This is a place of incredible white sand beaches, turquoise seas, flower strewn meadows, rocky shorelines, awe-inspiring views and peace and tranquillity.

With Gaelic as the first language, the Outer Hebrides still retains a culture distinct from the rest of Scotland. Here you'll find a sense of pride and tradition which make the region a remarkable and unforgettable place to visit.

After time on the Isles of Barra and Vatersay, our journey heads north using ferries and causeways to hop between the islands of Eriskay, South Uist, Benbecula, North Uist, Berneray, Harris and Lewis before we end on the Atlantic Coast at the Butt of Lewis. As part of trip, we will be staying in Tarbert on the Isle of Harris and its here where we will get the opportunity to visit the Isle of St Kilda, described as the island at the edge of the world. This is a once-in-a-lifetime opportunity to visit this magical place. For more information on the visit to St Kilda, check out https://www.visitouterhebrides.co.uk/our-islands/st-kilda

This trip offers you the opportunity and to experience and explore the islands’ wild landscapes, thriving wildlife, and ancient history stretching back 5,000 years. Key sights include Gearrannan's Blackhouse Village, the Standing Stones of Callanish, Luskentyre Beach, and The Golden Road.

You'll feel right at home in our carefully selected accommodations (mainly hotels or BBs), which provide a friendly atmosphere to relax after your cycling adventures. Enjoy dinner either onsite or at a local pub or restaurant nearby. The entire route follows smooth, paved roads, making it ideal for any type of bicycle. Please note on this trip, evening meals will be prebooked in advance and information will be provided in your bespoke trip itinerary, which will be sent to you about a week before travel.

We have a return transfer available from the north of England to Oban on the outward journey and returns from Ullapool which includes transport for cyclists, bikes and baggage. This must be booked at the time of booking as there is limited space available. Ask us for details. If you don't want the transfer, you can meet us in Oban. Long stay car parking is available in the town, just ask for details. Our trip starts in Oban on the mainland, before heading over by ferry to the Island of Barra and our first two nights stay in Castle Bay area, which is simply stunning and a great start to our cycling adventure in the Outer Hebrides and St Kilda!

Highlights

• Opportunity to visit the historic Gearrannan's Blackhouse Village on Lewis
• Opportunity to visit the Standing Stones of Callanish 
• Explore Isle of Barra and its impressive seascapes and beaches
• Witness the Loganair plane land on the tidal beach at Traigh Mor
• Enjoy the panoramic views, crystal clear waters and 
• Stay in good quality accommodation at selected good quality hotels and BBs throughout your stay
• The chance to visit a variety of quaint island villages 
• Experience a once in a life time opportunity to visit UNESCO world heritage site the Island of St Kilda, known as the island at the edge of the world!
• Experience world class cycling such as The Golden Road
• Experience wild Scottish landscapes, seascapes and an abundance of wildlife 
• Dine out at a variety of good quality local restaurants and hostelries

Itinerary

This is a fully guided and supported 10 day cycling trip. Itinerary as follows:

Day 1 – Sunday 16 May 2027

Arrival in Oban
Overnight stay in Oban is included in the price of the holiday. If you are arriving by car, the long stay car park is not far from the accommodation. If you are arriving by transfer bus, your bikes and bags will be unloaded at the accommodation. Once checked in, you will have the opportunity to explore the delights of Oban, our gateway to the Outer Hebrides and the start of our tour.

An evening meal has been booked in a local restaurant for everyone in the group to say hello and get to know each other.

Day 2 – Monday 17 May 2027

Ferry sailing Oban to Isle of Barra

After breakfast and checking out of our accommodations, everyone will meet at Calmac Ferry terminal nearby in Oban for the ferry crossing to Castle Bay, Isle of Barra. Your bags will be transferred by taxi from the accommodations to the ferry port. The ferry crossing takes about four and half hours. Once on the Island, it’s a very short distance from the ferry terminal to our accommodations and overnight stay in Castle Bay, Barra.

Please note, a group evening meal has been booked at a local restaurant or hostelry, for everyone to enjoy some local food and drink.

Day 3 – Tuesday 18 May 2027

Circular loop to explore the delights of Barra (33 miles/53km, ascent 2554 feet/778m)

After breakfast, everyone will meet outside The Castlebay hotel for a ride briefing with the Halcyon ride leader. Everyone will also have their bikes checked over by our mechanic at the start of the day. This is an anticlockwise circular social ride that takes in the stunning scenery of both the Isle of Barra and Vatersay. Cycling on these two islands offers quiet, scenic and mostly single track roads with dramatic coastal views and white sandy beaches and is a ‘highlights-heavy experience’. The route is graded as easygoing (2) to steady (3). Whilst parts of Vatersay and the west coast of Barra are undulating, the east coast near Castlebay is more rugged with very few ascents. One of the highlights on this ride is a visit to Barra airport, it’s the world’s only airport where scheduled flights land in a tidal beach, specifically the Traigh Mhor beach. Loganair operates Twin Otter aircraft from Glasgow, with landing times scheduled around the low tide when the sandy runways are safe from submersion. The experience is a sight to see with smooth, though often splashy, with flights operating twice daily. The ride includes a coffee and lunch stop. Ride ends back in Castle Bay.

Please note, a group evening meal has been booked at a local restaurant or hostelry, for everyone to enjoy some local food and drink.

Day 4 – Wednesday 19 May 2027

Ride from Vatersay to South Uist (30 miles/48km, ascent 1751 feet/533m) This leg includes a ferry journey from Barra to Eriksay.

After breakfast, everyone will gather outside The Castlebay hotel for a ride briefing led by the Halcyon ride leader. At the start of the day, our mechanic will also check all bikes. We will cycle from Castle Bay to the official starting point of the Hebridean Way on Vatersay, marked by the Hebridean Way Monolith/Obelisk near Vatersay Hall and the beach, directly across from the community hall. After taking some photos, our adventure kicks off as we head north, crossing the Vatersay causeway into Barra.

During the ride, we will encounter dramatic sea lochs, gentle hills, and pristine white sandy beaches while cycling the island of Barra. Covering around 18 miles, this section offers an ideal introduction to riding in the Hebrides. We’ll also take a short ferry from Ardmore on Barra to Eriskay, our next destination, with the trip lasting about an hour.

Eriskay is a magical island just three miles long and famously known as the landing site of Bonnie Prince Charlie in 1745 before the defeat at Culloden. After stopping for lunch at a local café, we'll cycle over the impressive causeway—keep an eye out for the Otters crossing sign—as we make our way to South Uist. From there, it's a brief ride to our next destination, Lochboisdale.

Please note, a group evening meal has been booked at either our accommodation or in a local restaurant or hostelry, for everyone to enjoy some local food and drink.

Day 5 – Thursday 20 May 2027 

Ride from South Uist to North Uist (63 miles/101km, ascent 1630feet/497m)

After breakfast, we will assemble outside the hotel, and the Halcyon ride leader will explain the next leg of our tour, from South Uist to Lochmaddy, North Uist. As we continue our journey northwards, the initial stretch of riding guides us through the distinctive watery landscape of South Uist. Along the way, we pass through Howmore, renowned for its scenic beauty and peaceful atmosphere. The route then leads us onto Benbecula, also known as the “Mountain of the Ford”. This name harks back to earlier times when traversing the Uists meant fording hazardous stretches of sand, only at low tide. Fortunately, those days are behind us, as modern causeways now connect the islands, providing safe and accessible paths for cyclists.

The next island on our itinerary is North Uist. Shortly after passing through the village of Claddach Kirkibost, we transition onto minor roads, which meander across the landscape and lead us to Lochmaddy. Lochmaddy marks our stop for the evening, offering a welcoming place to relax after the day's ride. For those feeling fatigued or if the weather turns unfavourable, there is an option to shorten today’s ride by 7 miles.

Please note, a group evening meal has been booked at either our accommodation or in a local restaurant or hostelry, for everyone to enjoy some local food and drink.

Day 6 – Friday 21 May 2027 

Ride from South Uist to Harris (49 miles/79km, ascent 2677feet/816m) * Please note we are staying in Tarbert for two nights.

After breakfast, we will assemble outside the hotel, and the Halcyon ride leader will explain the next leg of our tour, from South Uist to Harris. As we continue our journey northward leaving Lochmaddy, we set our sights on Tarbert as we continue our route through these stunning islands. Riding north, we follow the coast road to the Isle of Berneray, yet another place rich in wildlife and history. It is here that we take the short ferry across the Sound of Harris to Leverburgh. The crossing offers good opportunities to see seabirds, seals and maybe a sea eagle if we are lucky! On arrival on the Isle of Harris, you will notice a significant change in the landscape with bold mountains dominating the west coast. Cycling on the Isle of Harris offers spectacular, challenging scenery, featuring dramatic rocky coastlines, white sandy beaches and the famed ‘Golden Road’. Harris is the “Jewel in the Crown” of the Outer Hebrides. From Leverburgh, we follow the west coast road with incredible views – on clear days, the World Heritage Site of St. Kilda may be seen 40 miles offshore. Highlights here include Luskentyre Beach and bends of The Golden Road – a winding singletrack route through rocky east coast. Our ride ends with a great descent to the charming village of Tarbert where an excellent quality 4* hotel will be our base for the night. Tarbert is the main port on the Isle of Harris with several places to buy world famous Harris Tweed products.

Please note, a group evening meal has been booked at either our accommodation or in a local restaurant or hostelry, for everyone to enjoy some local food and drink.

Day 7 – Saturday 22 May 2027

Rest day, cycle around Harris, or visit to spectacular St Kilda, also known as the island at the edge of the world.

This is either a rest day with the opportunity to cycle on the Isle of Harris or probably one of the highlights of our tour of the Outer Hebrides is our visit to St Kilda, also fondly known as the island at the edge of the world. St Kilda is a remote archipelago one hundred miles off Scotland’s west coast and about forty-odd miles from Harris. It is recognised as the UK’s only dual UNESCO World Heritage Site for its immense natural seabird colonies and unique human history. It is home to the largest Atlantic puffin colony in the UK and 1 million seabirds. Inhabited for 4000 years, the last residents were evacuated in 1930, and it truly is a unique place to visit, and adds a sense of adventure to our tour! Please note this trip needs to be prebooked at the time of booking. This tour is subject to availability. Return transfer from Harris to Leverburgh is included in the excursion. Trip operated by St Kilda Sea Tours.

No group meal has been booked on this night due to the sea excursion to St Kilda and times of operation.

Day 8 – Sunday 23 May 2027

Ride from Harris to Lewis (44 miles/71km, ascent 2591feet/790m) *Please note we are staying in Callanish for two nights

After breakfast, we will assemble outside the hotel, and the Halcyon ride leader will explain the next leg of our tour, from Harris to Lewis. Another day of fantastic cycling awaits. Although climbing the hills of North Harris can be demanding at times, the scenery remains exceptional throughout the journey, culminating in an invigorating descent to sea level which includes the highest road climb in the archipelago before descending toward Leurbost. Additionally, this region offers excellent opportunities to observe both Golden Eagles and White-Tailed Eagles along the steep cliffs of Loch Seaforth. Once over on Lewis, we make sure there is plenty of time to check out the Standing Stones of Callanish near Loch Roag. The Stones are a magnificent 5000-year old Neolithic monument and predate Stonehenge and likely served a ritual or astronomical purpose. The place is usually quiet towards late afternoon, giving you time to explore this unique place. We cycle onwards to our hotel which is nearby, and our base for the next two nights.

Please note, a group evening meal has been booked at our accommodation for everyone to enjoy some local food and drink.

Day 9 – Monday 24 May 2027

Ride from Callanish to Butt of Lewis (38 miles/64km, ascent 1901feet/580m)

After breakfast, we'll gather outside the hotel for a briefing about our final ride from Callanish to the Butt of Lewis, marking the end of our Outer Hebrides tour. Our final route traces the west coast, featuring sites such as Dun Carloway Broch and the restored Blackhouse Village at Gearrannan, which showcases traditional island life. It’s worth a visit! Along the way, we'll pass the Whale Bone Arch at Bragar before reaching the Butt of Lewis on the Atlantic coast. After celebratory drinks, we return to Callanish for our last night in the Hebrides.

Please note, a celebratory group evening meal has been booked at our accommodation, to celebrate our epic trip, for everyone to enjoy some local food and drink.

Day 10 – Tuesday 25 May 2027

Return home

In the morning, we transfer from the hotel to catch the ferry back to Ullapool on the mainland from Stornaway with exact departure subject to the ferry schedule. We then transfer you back to either Oban to collect your cars or head south for home with our transfer service. This is an amazing drive with breathtaking scenery on all sides, allowing you a few more photo opportunities before we bid you goodbye.

Accommodation

Accommodation for this trip is in either good quality hotels or bed and breakfast establishments. We have a number of ensuite rooms, either twins or doubles or a number of rooms for sole occupancy or single rooms. Please note £150 sole occupancy supplement applies on this trip. Price is per person on a bed and breakfast basis.

The Cycling

Each individual ride is graded and detailed in the itinerary description. The rides on this cycling trip have been graded as 3, steady.

This trip is suitable for all bike types.

Group Size: 8-10 people.

Dates & Prices

16 - 25 May 2027, Price £2495. Sole occupancy supplement £150.

We also have a transfer available from north of England to include cyclists, bikes and baggage. The return transfer cost is included in the price. This must be booked at the time of booking as there is limited space available. If you decide to travel independently and do not book the transfer, you will receive a discount of £100 off (per person) from your holiday price. This will have to be done manually and is not automatic. The boat trip to St Kilda is extra and costs £300 and must be prebooked. See additional info section for more details.

The price stated is per person.

Additional Info

What’s Included:

• Accommodation (shared twin/double en-suite rooms or for sole occupancy) on a bed and breakfast basis in a vareity of good quality hotels and BB accommodation throughout the tour
• Services of a first aid trained ride leader and guide. Please note, we will use the services of a support vehicle and bike mechanic provided by local 5* review cycling business Bepsoke Cycles (Stonrnoway) Ltd
• Bespoke and detailed itinerary emailed to you personally a week before travel
• Return baggage transfer service fthroughout the tour
• GPX files emailed in advance of all the rides on this holiday
• Return transfer if booked from north of England to Oban outbound, return from Ullapool back to north of England
• Local Halcyon Cycling Holidays representative for the duration of the holiday
• Full financial protection (see booking conditions) 
• Return ferry for cyclists, bags and bikes
  

What’s Not Included:

• Bike and helmets 
• Travel or flight costs or charges for travelling with your bike (if applicable)
• Meals not stated in the itinerary
• Boat trip to St Kilda
• Travel insurance
• Personal clothing and equipment
• Personal expenditure (souvenirs, bar bills, hotel facilities etc)
• Entrance fees to cultural or historical sites and visitor centres
• Other optional activities
• Tips for guides, drivers, support staff
• Transfer costs such as local taxis, minibuses to meals booked at local pubs and restaurants

Transfer Information

A transfer service is available from north of England to Oban, returning from Ullapool. You will need to book your place at the time of booking. Limited spaces available and subject to availability. 

Pick-ups:

Start Sheffield Meadowhall Interchange M1 (South Yorkshire) Free car parking available here for duration of trip. You must park in the Interchange car park next to railway station.

Wakefield Junction 38 Woolley Edge Services Northbound M1 (West Yorkshire)

Huddersfield Hartshead Moor Services Westbound M62 (West Yorkshire)

Manchester Birch Services Westbound M62 (Greater Manchester)

Rivington Services Northbound M61 (Lancashire/Cheshire)

Lancaster Services Northbound M6 (Lancashire)

Please note the minibus and bike trailer will only pick up at certain stops prebooked in advance. Return to same place as outbound journey.

Bike Hire

Bike hire can be arranged in advance with a local bike hire company. Ask one of our team about arranging for bike hire at the time of booking as this is a special request. On all of our cycling holidays, wearing of a helmet is mandatory.

Visit to St Kilda

The boat trip to St Kilda is an optional extra and will operate on Saturday 22nd May 2027 only and is subject to availability. The cost is £300 and will be operated by St Kilda Sea Tours in Uist. The excursion leaves at 8am from Leverburgh and returns at 7pm. Trip operation is subject to weather conditions. 

Gallery