A Hebridean Island Odyssey – the Scottish Highlands & Islands


  • 744km / 465 miles
  • The ultimate Scottish islands ride
  • Have a Bike Staycation in 2018
  • Baggage vehicle & mechanical support
  • 9 Days / 8 Nights
  • Our package includes ALL ferry crossing charges
  • Explore 11 Hebridean islands
  • UK qualified bike guide
Number of Days: 9
2020 Land Only Price From: £1,695
Grade: Hot
Group Size: 6 – 14 (Smaller Groups by Arrangement)
View: Kit List


Sat 21 Mar – Sun 29 Mar 2020 
Sat 16 May – Sun 24 May 2020 
Sat 30 May – Sun 7 June 2020 

Dates are available for Private Groups by arrangement –
Contact us for details on 01768 778848

Trip Overview

Day 1 Arrive, Ride & Sail

Our trip starts in the pretty Scottish West Coast port town of Oban. We meet up as a group at 10:00 am as this allows us to get the support van all packed and organised with your kit well before the ferry check in time. As our first ferry crossing isn’t till mid afternoon we take the opportunity to have a short shake down ride. We then catch the Calmac ferry to Barra – and get the longest single sea crossing (4 hrs 50 mins) of our trip out of the way on Day 1. A wee dram will be in order tonight as we are now in Whisky Galore country!
23km / 14 miles. Overnight in a hotel. Meal/s included: L, D

Day 2 Four Island Day

Today might be a short day but it’s a stunner of a ride. In the morning we ride out from Castlebay and cross over to the island of Vatersay via the causeway. After an explore of Vatersay we cross back to Barra and ride round the West Coast of the island with stunning views out over the Atlantic Ocean – next stop North America! Barra is known for it’s beach airport to we take a spin past there en-route to Ardmhor for our short ferry crossing over to the island of Eriskay. Arriving in Eriskay we then start the next leg of today’s ride to Lochboisdale on South Uist, via another causeway.
57km / 36 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 3 Carry On Up the Archipelago

The Uists and Benbecula are a stunningly beautiful chain of islands, especially in spring and early summer when the machair is ablase with a riot of colourful wild flowers. Today is the flattest day of the trip, with only 152m of climbing, so lets hope that the prevailing SW wind is prevailing today, as that will give us a nice tail wind as we ride the length of South Uist, Benbecula and North Uist archipelago. We’ve no ferry crossings today as these islands are all linked by causeways.
102km / 64 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 4 The Real Tweed Run

We start with a short 10 mile ride from Lochmaddy to our next ferry port on the island of Berneray, which is linked by causeway to North Uist. A cracking ferry crossing threads through the skerries in the Sound of Harris and we then land on the next island of our trip Harris. The island is world famous for it’s Harris Tweed. We ride up the East Coast of Harris on the “Golden Road”, where it soon becomes apparent that the flat terrain of the Uists is definately behind us, before stopping at Tarbert for lunch. In the afternoon we ride out to the fascinating small island of Scalpay before returning back through Tarbet and over to Harris’s stunning West Coast and one of our all time favourite beaches. The day finishes with the short ride back to Tarbert and our hotel for the night.
105 km / 65 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 5 Stone Me

Today we’ve a phenominal out and back ride across the mountains to Isle of Lewis to the neolithic Callanish Standing Stones – think Stonehenge but in a strikingly remote and dramatic setting overlooking the Atlantic Ocean. Callanish marks the Northernmost point of our trip and we ride back across the mountains to Harris. Once again our route skirts the flanks of Clisham which, at 799m, is the highest point in the whole Outer Hebrides archipelago.
126km / 78 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 6 Skye High

Our ferry “over the sea to Skye” departs at 11:50 today so there’s some time in the morning to explore the fishing port and island hub of Tarbert before we say goodbye to the Outer Hebrides. We have lunch on the Calmac ferry today and the crossing to Uig on Skye only takes an hour and 40 minutes. Arriving on Skye we turn North around the lumpy Trotternish peninsula, past ancient Duntulm Castle and the stunning rock formations of the Quiraing before dropping back down to sea level and the island’s capital Portree.
56km / 35 miles. 56km / 35 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 7 The Winged Isle Tour

Due to it’s numerous peninsula’s Skye is also known as the Winged Isle and is also home to the UK’s most rugged mountain range – the Cuillins. Today’s route is a stunning ride over challenging terrain which allows us to explore and see some of the best of Skye. The day starts with a loop around to the West of the island passing historic Dunvegan Castle before cutting back across to the East at Sligachan. From here our route skirts around a fijord like sea loch before heading over a pass and then rejoining the coast once more. The last leg of the day sees us riding down the beautiful Sleat peninsula to Armadale before catching our ferry back to the mainland …. and Mallaig.
122km / 76 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 8 Westward Ho

Today’s route is a sure candidate for one of my favourite days riding in Scotland …. it’s also the most mountainous day of this trip with over 1,300m of ascent. There’s a couple of big climbs but for the most part is just constantly up and down over stunning roads and we nearly always have a sea view. Leaving the bustling fishing port of Mallaig we head South then East till we get to Lochailort. From here we ride through the historic district of Moidart and stop for lunch overlooking Castle Tioram, the ancient seat of the Clan MacDonald of Clan Ranald. Next we ride West on narrow, single track roads to Arnamurchan lighthouse – the most Westerly point on the mainland of the UK. Finally, we cross over to the Isle of Mull and our hotel for the night in the bustling island capital of Tobermory.
119km / 74 miles. Overnight in a hotel. Meal/s included: B, L, D

Day 9 Final Isle / Departure Day

Leaving the multi couloured houses of Tobermory behind us our route today tracks down the side of the Sound of Mull. It’s our final island fling and you’re sure to enjoy the last of the magical Hebridean Islands that we’ve been exploring over the last week. A rolling start gives way to flat roads at Salen and final few miles to Craignure, and the Oban ferry, give us a great opportunity to savour the journey we’ve just completed. A short 45 minute crossing delivers us back to the mainland once more and journey’s end in Oban. We aim to back in Oban for 14:00.
34km / 21 miles. Meal/s included: B

What’s Included

  • 8 nights accommodation*
  • All meals as detailed in the trip overview.
  • Meal Key: B – Breakfast, L – Lunch, D – Dinner. Please note that all lunches are picnic style and are designed to suit cyclist’s appetites.
  • All ferry crossings on the trip as per the itinerary.
  • All baggage transfers in our baggage vehicle.
  • The services of a Rather Be Cycling, UK qualified, Bike Guide.
  • The services of a Rather Be Cycling baggage vehicle driver / assistant.
  • Access to commonly required tools, mechanical advice & assistance.* All accommodation is allocated and priced on a twin occupancy basis. Please contact us for Single Occupancy Rates.

What’s Not Included

  • Travel to and from Oban – the starting & finishing point of the trip.
  • Long term car parking, if required, in the Oban area.
  • Suitable Travel Insurance covering you for road biking – recomended.
  • All drinks e.g. bottled water, coffees, teas, alcohol, etc.
  • Entry fees e.g. to visitor attractions, etc.
  • Spare / replacement bicycle parts & accessories e.g. tyres, tubes, brake bloacks, wheel/s, etc.
  • Other expenses e.g. souvenirs, additional food, laundry, etc.
  • Tips – at your discretion.

Bike Spec

  • This is a road cycling weekend holiday and a road, sportive or touring bike is ideal for this trip. We recommend 700x23c tyres and have found Michelin Pro 3 & 4 tyres to perform very well. Compact or triple gearing giving a bottom gear of between 30″ and 40″ is suggested for this trip. Alloy rims or carbon rims with alloy braking surfaces are preferable to full carbon rims for this trip.
  • Although modern stiff soled road cycling shoes are fine for this trip you might want to consider SPd shoes & pedals (or having some flip flops handy in the van) as Calmac insist that all bikes are walked on and off their vessels – having seen people take falls on the slippery slipways and ramps we agree with their policy 🙂
  • Your bike should be fully serviced, and thoroughly tested, before your holiday.