Guided Sailing & Hiking in Scotland’s Hebridean Islands 2027
For those who seek adventure—under sail and on guided hikes across Scotland’s wild isles.
Embark: Saturday, 14 August 2027, at 13:30 in Oban
Disembark: Monday, 23 August 2027, at 9:00 in Oban
Duration: 10 days
Discover the wild beauty of the Hebrides on a perfect mix of sailing, hiking, and pure, unspoiled nature. Sail among the enchanting Small Isles and the dramatic landscapes of Skye, where every island reveals its own character and charm. Onboard Steady, you’ll enjoy cosy comfort, delicious meals, and the freedom to explore awe-inspiring destinations each day. Whether it’s your first time or you’re a seasoned adventurer, we—Jan-Willem and Mariëlle—will guide you both at sea and on land.
No sailing experience needed, only a love for adventure!
Highlights of the Voyage
- Guided walks – Explore rugged cliffs, serene beaches, and breathtaking landscapes.
- Mull & Tobermory – Wander the colourful harbour town with cosy pubs and unique shops.
- Loch Scavaig & Cuillin Mountains – Hike through Skye’s dramatic and untamed scenery.
- Eigg & An Sgurr – Climb the iconic peak for 360° views of the Small Isles.
- Wildlife spotting – Look out for minke whales, dolphins, seals, and majestic sea eagles.
Day-to-Day Programme – Highlights of Guided Hikes
Day 1: Embark in Oban & Sail to Loch na Droma Buidhe
Board at 13:30 in Oban and sail through the scenic Sound of Mull. Overnight at anchor in Loch na Droma Buidhe.
Day 2: Sail to Canna – Wildlife & Serenity
We set sail to Canna, spotting dolphins and seals along the way. Relax in the peaceful surroundings upon arrival.
Day 3: Guided Hike on Canna – Cliffs & Views
- Distance:15 km / 7.50 miles / grade 2 (Moderate walk)
- Duration: 4 hours
Walk along Canna’s southern shore past Canna House and the farm before heading inland across moorland to Beinn Tighe. Explore rugged cliffs and gentle hills, and discover two hidden Neolithic souterrains. Finish with a tasty lunch at the cosy Canna Café, featuring local produce.
Afternoon: Sail to Rum.
Day 4: Guided Hike on Rum – Wild Hills & Wildlife
- Distance: 10 km / 6 miles / grade 2 (Moderate hillwalk)
- Duration: 4 hours
Hike streams, waterfalls, and rugged hills. Spot red deer and sea eagles.
Afternoon: Sail to Skye
Day 5: Guided Hike on Skye – Loch Scavaig & Cuillin Mountains
- Distance: 7 km / 4.25 miles / grade 2 (Moderate walk)
- Duration: 3–4 hours
Hike around Loch Corusk under the dramatic Cuillin Mountains. Optional swim in crystal-clear waters.
Afternoon: Sail to Eigg
Day 6: Guided Hike on Eigg – An Sgurr & Panoramic Views
- Distance: 8 km / 5 miles / grade 3 (Moderate to challenging hillwalk)
- Duration: 3–4 hours
Climb the iconic An Sgurr for 360° views over the Small Isles and Skye.
Afternoon: Sail to Muck.
Day 7: Guided Hike on Muck – Hidden Gems & Tranquil Shores
- Distance: 7 km / 4.25 miles / grade 2 (Moderate walk)
- Duration: 3 hours
Walk along serene beaches, rolling fields, and coastal paths. Optional stop at the local tearoom.
Afternoon: Sail to Tobermory
Day 8: Tobermory – Colourful Harbour Town
Explore its colourful waterfront, quaint shops, and cosy pubs. A relaxed day after several guided hikes.
Afternoon: Sail to Loch Aline or Duart Bay to visit the Castle on the Isle of Mull
Day 9: Guided Hike on Kerrera – Coastal Walk
- Distance: 16 km / 10 miles / grade 2 (Moderate walk)
- Duration: 4–5 hours
Enjoy a scenic guided walk with stunning views over Oban Bay. In the evening, celebrate the journey with a festive Captain’s Dinner onboard.
Day 10: Farewell in Oban
Final sailing leg to Oban. Disembark at 09:00, leaving with unforgettable memories of your Sail & Walk Holiday.
Sailing with the Elements: The Hebrides’ untamed beauty comes with ever-changing conditions, making each voyage truly one of a kind. Our itinerary serves as a guide, but we embrace flexibility, adjusting the route to match the weather. This ensures your safety while infusing every adventure with a touch of the unexpected.
Walking difficulty
Our guided walks cover varied terrain, including steep and exposed sections. A good level of fitness and a head for heights are essential.
Grade 2 – Moderate walks
Slightly more demanding hikes. Paths may be narrow, uneven, or occasionally indistinct.
Grade 3 – Moderate to challenging hillwalks
Rugged terrain with steeper ascents and descents, requiring good balance and confidence on hills.
Wildlife Encounters
Sailing with Steady offers incredible wildlife experiences:
- Puffins, razorbills, and guillemots along the cliffs
- Soaring sea eagles
- Red deer and occasional otters onshore
- Curious seals, playful dolphins, and occasional whales, including Minke and even orcas
Binoculars are highly recommended – you never know what might appear next!
Who Is This Adventure For?
- Active explorers: Perfect for travellers who enjoy a mix of sailing and onshore exploration.
- Nature lovers: For those who appreciate the tranquillity and stunning landscapes of the Scottish Highlands.
- Small-group adventurers: Ideal for guests who enjoy a hands-on, social, and informal onboard atmosphere
- Ages 16–75: No prior sailing experience required, but enthusiasm and curiosity are essential.
- Flexible and engaged: Guests who are happy to participate in onboard life and enjoy an interactive sailing experience.
Onboard Catering
Enjoy freshly prepared meals made with care by Mariëlle, using local ingredients whenever possible. Vegetarian and dietary preferences are accommodated (except vegan).
All meals and accompanying drinks (tea, coffee, milk, orange juice) are included.
Lunches
During our combined sailing and hiking trips, we regularly have lunch ashore. Depending on the route and conditions, we sometimes prepare lunchboxes for you to carry in your backpack. At other times, we may stop at a local eatery for lunch, which will be at your own expense.
One evening, we’ll dine ashore at your own expense, with the day determined by the schedule.
On board, red and white wine and beer are available for purchase.
We do not serve spirits, and we kindly ask guests not to bring any on board.
For safety and to maintain a positive atmosphere on board, the use of excessive alcohol consumption is strictly prohibited, and alcohol is not permitted before or during sailing.
All Hands on Deck!
Participate in sailing, help in the galley, or enjoy the camaraderie onboard. Together we create a lively and welcoming atmosphere.
Price
• €2,500,- (shared cabin)
• €3,750,- (single occupancy of a double cabin, 50% surcharge)
Exclusive Youth Discount: Get 10% off for participants up to 29 years old!
Included:
- All meals on board (breakfast, lunch and dinner), including hot drinks (exept for 1 dinner ashore)
- Bedding (pillow, sheets and duvet) and one wash towel
- Professional crew and sailing instruction
- Guided walks
- Marina and fuel fees
- All tender transfers to and from the boat
Excluded:
- Alcoholic and soft drinks
- 1x dinner ashore
- Flights; transit or overnight hotels
- Travel to and from the boat on embarkation and disembarkation days
- Travel insurance
- Personal expenses
Getting to the Ship
Travel Advice: Oban
Oban is accessible via Glasgow, with daily trains or buses offering scenic 4-hour journeys. Plan your travel to arrive in time for boarding at 13:30.
Location:
- Oban: North Pier Pontoons, Oban PA34 5QD, Argyll, Scotland
Click here for more info on how to get to Oban.
Booking & Travel Info
Booking is easy: complete our booking form, and we’ll send you a no-obligation quote. Once confirmed, your adventure is secured.
Important Travel Information
Electronic Travel Authorisation (ETA) is required to enter the UK.
- Cost: £19
- Valid for 2 years or until your passport expires
- Apply at: www.gov.uk/get-an-eta
For questions or to book, click here – we’re happy to help!
This trip is covered by the STO Garant scheme. For more information, visit STO Garant.
