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Hebrides Tip to Toe

150 miles of cycling, trekking and sea kayaking on this brilliant journey

Experience an unforgettable multisport adventure across the wild Outer Hebrides in Scotland with this epic north-to-south island crossing by bike, foot and sea kayak. Traversing 150 miles from the Butt of Lewis to Vatersay, this fully supported endurance challenge journeys through remote Atlantic coastlines, rugged islands, causeways and breathtaking Scottish landscapes. Combining cycling, trekking and kayaking with accommodation, meals, logistics and mechanical support included, this is the ultimate Hebridean adventure expedition. 

Aerial view of participants kayaking through clear, blue water
Enter

Dates

25th - 29th September 2026

24th - 28th September 2027

Duration

5 Days / 4 Nights

Distance

166 miles on bike (267 km)
8 miles on foot (12km)
12 miles in kayak (19km)

Event Type

Bucket List Adventures

Highlights

Three cyclists riding along a road with rocky, grassy terrain behind

Cycle to the Callanish Standing Stones

Pedal through the wild landscapes of Lewis to the extraordinary Callanish Standing Stones, a 5,000-year-old prehistoric site older than Stonehenge and steeped in mystery.

Participants lifting kayaks from water and placing them on sandy beach

Seal and dolphin spotting along shoreline

Keep your eyes peeled for seals bobbing beside your kayak and dolphins breaking through the waves as you travel along the rugged Hebridean shoreline.

Aerial view of participants kayaking through clear, blue water

Paddle the Sound of Harris

Glide across the crystal-clear waters of the spectacular Sound of Harris by sea kayak, weaving between remote islands, white sand beaches and some of the most breathtaking coastal scenery in Scotland.

Aerial view of sandy coastline and clear water

Cycle across white sand beaches

Cycle across the astonishing white sand beaches of the Outer Hebrides, where turquoise waters and vast open horizons make you feel a world away from Scotland as you know it.

Itinerary

'Hebridean Way' rusty sign and bright, blue sky behind

Day One: Friday

Meet the team, park up, and settle in before our transfer north to Ullapool, where we’ll board the ferry to Stornoway. During the crossing, we’ll kick things off with initial briefings and the chance to grab some food, before arriving, sorting kit and getting an early night ahead of the adventure.

Cyclists riding along coastal road, with sandy beach to one side and green field to the other

Day Two: Saturday

We begin with an early transfer to the Butt of Lewis, the northernmost tip of the Outer Hebrides, where our adventure starts beneath its iconic lighthouse. From here, we ride south on quiet roads through the wild landscapes of Lewis, visiting highlights like the Callanish Standing Stones, with regular pit stops to keep you fuelled.

Crossing into Harris, we swap bikes for a scenic coastal run before a punchy ride over dramatic mountain passes, finishing at the southern tip of the island in Leverburgh.

Aerial view of participants kayaking through clear, blue water

Day Three: Sunday

If conditions allow, we’ll take on an unforgettable sea kayak crossing of the spectacular Sound of Harris, paddling through crystal-clear shallows dotted with islands and rich in marine wildlife. If the weather has other ideas, we’ll switch to Plan B and make the crossing by ferry.

Back on land, we ride south through Berneray, North Uist, Benbecula and South Uist, with the chance to cycle across an incredible white sand beach before finishing the day at Eriskay and heading to our accommodation.

Highland cow stood in field with sunny sky above

Day Four: Monday

Weather permitting, we begin with another spectacular sea crossing over the Sound of Barra before getting back on the bikes for the final push south. A short but rewarding hike takes us to the summit of Heaval for sensational island views, before one last ride to our unforgettable finish on the stunning beach at Vatersay, among the famous feral cattle.

Participant walking over frozen, snow-covered ground

Day Five: Tuesday

An early start sees us checking in for the ferry back to the mainland, sailing into Oban before transferring back to Tyndrum. We expect to arrive back mid-afternoon, where you can collect your car or connect with onward travel—phew, what an adventure.

Rocky shoreline and colourful sky with hills in the background
Man climbing up snowy slope

Your Adventure Leader

Tom

Tom thrives in remote, extreme and challenging environments, from dense jungle and scorching deserts to sub-zero wilderness and high-altitude terrain. With experience designing and leading expeditions in over 30 countries across 6 continents, he brings serious adventure expertise to every project. Tom is qualified as a Mountain Leader, Wilderness Emergency Medical Technician and HEAT-trained expedition professional, with additional certifications across climbing, mountain biking, paddle sports and off-road driving.

Highland cow stood in field with sunny sky aboveChildren-with-Cancer-UK-logo-white

Raise £4000 and get up to £2000 refunded

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FAQs

Is the route likely to change?

The very nature of adventure means that the unexpected can sometimes become part of the journey and that is all part of the experience. While we will always strive to deliver “Plan A”, there may be occasions where operational, safety, weather or environmental factors require us to adapt plans and implement contingency routes or alternative arrangements.

As with all Rat Race adventures, participant safety and overall event delivery remain our highest priorities. We therefore reserve the right to amend routes, itineraries or logistics where necessary, using the experience and judgement of our expedition team to make the best decisions on your behalf in changing conditions. Wherever possible, we will communicate any changes in advance. More often than not, these unexpected moments become part of the adventure itself adding to the stories, memories and unique character of the experience.

How do I enter?

Click 'Enter' and sign into your Rat Race account and follow the sign up procedure. If you need any assistance please drop the customer service team an email on events@ratrace.com

How old do I need to be?

Rat Race require you to be over 18 on the day of Registration for this adventure.

Can I transfer my entry?

If you find yourself unable to join us on the start line of this event, you are able to transfer your entry into an event credit voucher once for use on a new entry into an event of your choice. Transfers must be requested within the qualifying transfer window to be accepted and processed. Credit vouchers are valid for 12 months from the date of issue. Credit vouchers are exempt from the transfer process. To find out more information and how to submit a request, view of full transfer policy HERE 

Can I fundraise for charity?

You are very welcome to fundraise for any charity close to your heart while taking part in the event. Please note, however, that our Charity Refund Offer applies exclusively to participants fundraising for Children with Cancer UK.

Can I volunteer?

You can view our current volunteer positions here

Can I go at my own pace?

Yes, there are cut-offs on the event, but these are based purely around the available daylight hours each day. Our aim is to help everyone complete the adventure, so if you fall behind the required pace and are unlikely to reach the end before nightfall we will transport you forward. You are then welcome to restart again the following day. This is not an event where missing a cut-off means your adventure is over.

What is Refund Protect?

Add Refund Protect to your booking during purchase and receive a full refund of your entry fee if you are unable to attend the event due to a qualifying unforeseen circumstance. PLEASE NOTE this protection is with our 3rd party partner Refund Protect and NOT Rat Race. In the event you make a refund application this is administered by the Refund Protect customer service team, Rat Race are not privy to the application and cannot intervene on your behalf to influence the outcome determined by their team.

To add Refund Protect (administered by a 3rd party) to your Rat Race booking simply select this option when presented during the entry process. Refund Protect cannot be added retrospectively. Rat Race will then send you name and booking details to Refund Protect in order to protect your transaction with them. If you opt to pay in instalments and transfer your entry before the entry cost is full paid you will be liable to ensure the cost of Refund Protect has been fully covered. This total amount will be deducted from any Rat Race credit due through the transfer process or you will be invoiced by Rat Race for the outstanding amount as Rat Race have paid this on your behalf to Refund Protect at point of entry. 

Do I need insurance?

Yes. Comprehensive travel insurance is compulsory for this event and must cover both general travel and participation in the outdoor endurance activities included within the itinerary. You will also require Evacuation Insurance, which covers emergency extraction and onward medical transport by helicopter or similar should urgent assistance be required in this remote environment.

We strongly recommend arranging your insurance as soon as you enter the event and booking flexible flight options where possible to allow for any unexpected changes. Please ensure your chosen policy specifically covers the activities you will be undertaking during the expedition. There are a number of specialist adventure travel insurers available, including Mann Broadbent.

What kit do I need?

Trekking or trail running

• Trail running/walking footwear or lightweight boots

• Daypack (Ultra running vest or a small backpack – between 10 and 20 litres)

• Water carrying capacity minimum 1.5l

• Trail running/walking apparel – shorts, technical wicking tee/ base layer, long-sleeved wicking layer, mid-layer (e.g. microfleece)

• Waterproof upper body and leg cover 

• Buff or similar neck gaiter, and sun hat/cap 

• Spare base and mid layers

• Socks; consider neoprene and GoreTex, as well as warmer sport socks. Also consider a 2-sock system with a toed liner sock (e.g. ininji) and an outer, cooler trekking sock. We are told our own Rat Race Merino socks are pretty good, too!

• Blister care kit

• Personal bivvy bag 

• First Aid kit 

• Water bottle, and/or cup or Hydration system for rucksack 

• Headtorch, waterproof to IPX7 standard, minimum 150 lumens + spare batteries or second headtorch. 

• GPS device or smartphone

Bike Stages

• Road bike or gravel bike (your own or hired)

• Bike shoes and cleats (optional – hire bikes will be provided with flats but you may substitute with cleats as required)

• Cycling jersey

• Cycling shorts

• Cycling gloves

• Cycling waterproofs inc (recommended) booties

• Water carrying capacity minimum 1.5l (as with foot sections – bottles, soft flasks or bladder systems are all fine – or a combo)

• Bike handpump. We will carry a track-pump with us on each support vehicle.

• Bike multitool

• Bike puncture repair kit – to include spare inner tubes, slime (if you use it) or spare CO2 canisters

• Handlebar Mount for a smartphone or GPS device (so you can view the route when sat on your bike)

• Front and rear bike lights

• Some form of hi-vis top/patches for road cycling

• Basic bike spares and tools to include: spare chain, brake pads, inner tubes, spare tyre

• Puncture repair kit (or tyre repair kit if tubeless)

• Pump/CO2 canisters

• Small toolkit, inc multi-tool

• Chain tool

• Tyre levers Bikes must be fully serviced prior to the event and any work parts replaced as access to specific spares is very limited on the islands.

Water stages - kayak

• Buoyancy aid, paddle and kayak will be provided

• You should dress in waterproofs and technical wicking undergarments. These can be the same ones you have used on the run or ride stages. Please remember you will be sitting stationary and WILL get wet. Avoid cotton and use technical wicking fabrics

• If you do have kayaking gear, such as a cag or over-trousers, then please do bring these

• Sandals, boat shoes or any permeable trainers

• A dry bag and/or waterproof rucksack liner (or a selection of small and larger ones) will be essential to stow gear and food inside your kayak gear stowage chambers; to ensure it does not get wet.  The kayak stages are not huge but they are exciting and committing sea legs and could be subject to swells and fairly ‘robust’ weather (!). They are also at the start of each day, after which you have long outings on the bike. Bottom line on the kayak legs: Try and wear quick-drying gear or stuff you can get wet and then discard and change into other clothes once you land. There will always be the option to access your support bag after these sections of course. 

Do I need to be able to kayak?

The kayaking is an exciting part of this format. However, these Isles, their sea conditions and their weather can be variable to say the least. Which means it is not a-given that we will kayak. The sea crossings will always be subject to an assessment by our safety team on prevailing conditions and they will only set out on the sea legs if they are satisfied that conditions are in tolerances. If we do have to cancel any of the 2 sea crossings, the contingency is very easy: We simply take the ferry across the Sounds. The vehicles will be going on the ferries anyway. It’s still exciting from the deck of the ferry! 

The standard we will require when you turn up is that you are happy in a closed-cockpit boat; you are familiar with self-rescue techniques and that you are confident as a novice sea paddler, paddling as part of a group. You will never be without one of our staff on this sea leg, so we class this as a ‘guided’ crossing. All of these skills are easy to gain on a one day sea kayak experience day. 

What kind of bike do I need?

The optimum machine to enjoy every inch of this biking route is a gravel bike. This is by no means essential however. A road bike will be absolutely fine and for 95% of the journey, we are indeed on roads. We do have our rather unique beach riding section at the bottom of South Uist. It will be a bit difficult on the sand for uber-skinny road bike tyres, but a gravel bike will chew it up. However, the road bikes can ‘have a go’ if you wish. Or there is a road that runs parallel which you can take, if you prefer to use a road bike for the full trip. Ultimately it is ALL road except this beach section (around 6 miles). 

Pricing

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We’ve created a flexible, interest-free* instalment plan so you can choose how many months to spread the cost of your adventure. Choose to pay in full or in equal monthly instalments up to 3 months before your event date.

​* Once you sign up, Rat Race will set up a recurring monthly payment via Stripe. If a payment fails, you’ll receive reminders from Stripe and our team. After three failed contact attempts and no payment, your entry will be cancelled with no refund or transfer eligibility.

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