10-26. Guided Sailing & Hiking Holiday: Skye & The Small Isles

Guided Sailing & Hiking Holiday:

Skye and The Small Isles 2026

Embark: Sunday, 19 July 2026, at 17:00 in Oban

Disembark: Wednesday, 19 July 2026, at 10:00 in Oban

Duration: 11 days

Get ready to uncover the wild beauty of the Hebrides—a perfect mix of sailing, hiking, and pure, unspoiled nature.

Onboard Steady, you’ll enjoy cosy comfort and delicious meals as we chart a course to new and 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 through this unforgettable journey, both at sea and on land.

Highlights of This Voyage

Guided walks through the Hebrides – Discover rugged cliffs, serene beaches, and breathtaking landscapes.
Explore Mull and the colourful harbour of Tobermory – Wander through charming streets, cosy pubs, and unique shops.
Hike to Loch Scavaig and the dramatic Cuillin Mountains – Experience the wild beauty of Skye’s iconic landscapes.
Climb Eigg’s iconic An Sgurr – Take in spectacular 360° views of the Small Isles and beyond.
Sail through pristine waters and spot wildlife – Look out for puffins, dolphins, and majestic sea eagles.

Day-by-Day Itinerary

Day 1: Welcome Aboard in Oban

Your voyage begins in the bustling harbour town of Oban, where Steady awaits at the marina near North Pier. At 17:00, we’ll warmly welcome you aboard. Meet your fellow adventurers, settle in, and explore the ship. Over a delicious shared dinner, we’ll raise a glass to the exciting days ahead and share all the details of your upcoming adventure.

Day 2: Easy Sailing to Tobermory

We ease into the voyage with a smooth sail through the scenic Sound of Mull. By midday, we’ll arrive in Tobermory, famous for its colourful waterfront and welcoming charm. Stroll the quaint streets, indulge in cosy pubs, or browse the unique shops. It’s a perfect, laid-back start to your Hebridean adventure.

Day 3: Canna – A Wildlife Wonderland

Hoist the sails as we head to Canna, the most secluded of the Small Isles. Keep watch for playful dolphins and inquisitive seals along the way. Once on Canna, you’ll find a haven of wild meadows, dramatic cliffs, and serene beauty. Anchoring in these quiet waters feels like stepping back in time.

Day 4: Walking on Canna – Puffins and Perfect Views

Today is a highlight for nature lovers! Our guided walk takes you across Canna’s unspoiled landscapes, along dramatic cliffs and gentle hills. The Sanday cliffs steal the show, home to puffins and soaring seabirds. We’ll pause for a picnic amidst the island’s raw beauty – a day of awe-inspiring moments you won’t forget.

Day 5: Loch Scavaig – Skye’s Untamed Beauty

Prepare to be amazed as we sail into the breathtaking Loch Scavaig, cradled by the iconic Cuillin Mountains. Here, we’ll embark on a hike around Loch Corusk, one of Scotland’s most enchanting spots. For the adventurous, there’s the chance to take a dip in its crystal-clear waters – a memory to cherish forever!

Day 6: Rum – Wild Hills and Majestic Wildlife

Our next destination is Rum, where towering hills and untouched wilderness await. As we hike, you’ll cross streams, pass cascading waterfalls, and may even spot red deer or majestic sea eagles. Rum’s rugged charm and tranquil atmosphere make it a nature-lover’s dream.

Day 7: Eigg – An Sgurr and Unforgettable Views

Eigg calls, with its iconic peak, An Sgurr, beckoning us to climb. This volcanic marvel offers a thrilling hike and jaw-dropping views over the Small Isles, Skye, and beyond. After your adventure, reward yourself with a visit to the island’s friendly local pub – the perfect way to unwind.

Day 8: Muck – Hidden Gems and Tranquil Shores

We’ll explore Muck, the smallest of the Small Isles, celebrated for its serene beauty and welcoming community. This charming island is home to just a handful of residents, creating a sense of peaceful seclusion. Known for its golden sandy beaches, fertile farmland, and stunning coastal views, Muck offers a perfect escape from the modern world. After a scenic walk through rolling fields and along quiet shores, indulge in homemade treats at the island’s cosy tearoom, renowned for its warm hospitality and delicious offerings. It’s a day of simple pleasures and natural beauty, leaving you refreshed and inspired.

Day 9: Loch Aline – A Stroll Through Ardtornish Garden

Sailing through the Sound of Mull, we’ll arrive at Loch Aline. Here, the enchanting Ardtornish Garden invites you to wander through vibrant flowerbeds, tranquil paths, and a historic estate. It’s a day to relax, breathe in the fresh air, and soak up the beauty of the Hebrides.

Day 10: Kerrera – Scenic Walks and a Festive Farewell

Our final sailing day takes us to Kerrera, a peaceful island just off Oban’s coast. With its scenic paths and stunning coastal views, it’s a walker’s paradise. In the evening, we’ll gather aboard Steady for a festive Captain’s Dinner, celebrating the incredible experiences we’ve shared.

Day 11: Farewell in Oban

After a hearty breakfast, we’ll return to Oban Marina by 10:00 AM. Though it’s time to say goodbye, you’ll leave with cherished memories of your sailing and walking adventure – and perhaps already dreaming of your next visit to the Hebrides.

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.”

Are you ready to experience the magic of the Hebrides? Let’s make it unforgettable!

Wildlife

Sailing with Steady promises amazing wildlife encounters. You’ll often see seabirds like puffins, razorbills and guillemots, while sea eagles soar majestically along the rugged coastline. On land, keep an eye out for red deer, and with a bit of luck, you might spot an otter in the bay. The seabird colonies, especially during the breeding season, create a cacophony of sounds that echo off the cliffs. As we sail through Scottish waters, you may also spot seals curiously poking their heads above the water or sunbathing on rocks.

Dolphins are frequent visitors, with common dolphins, bottlenose dolphins, and white-beaked dolphins often playing alongside the boat. Occasionally, we spot Risso’s or white-sided dolphins, and Minke whales are common. On rare days, you might even see humpback whales. The real stars of the show, however, are the local pod of orcas — an unforgettable experience if you’re lucky enough to see them. Make sure to keep your binoculars handy!

For Adventurous Hikers: Scenic Trails with a Twist

Love a good hike with a bit of a challenge? Our trails are perfect for active explorers who enjoy hilly terrain and breathtaking scenery. The routes range from 10 to 18 km, offering a mix of gentle slopes and steeper sections. You’ll walk through rugged rocky paths, boggy grasslands, and untouched landscapes that’ll make every step an adventure.

No need to worry about being over-prepared—we’ll send you a handy packing list before the trip, so you’ll know exactly what to bring in your daypack.

These hikes are for those who love nature at its rawest and most beautiful, with trails that take you off the beaten path. And the best part? You won’t be alone. Jan-Willem and Mariëlle will guide the way, making sure you discover the most stunning spots together with the group.

Ready to lace up your boots? Let’s hit the trails and explore!

Is This Adventure Calling You?

This trip is perfect for those who enjoy an active yet relaxing holiday and love exploring new places in the company of fellow travelers.

Ideal for nature enthusiasts, hikers, and sailors who appreciate active holidays in pristine surroundings.
Hikes range from 10 to 18 km, taking you over sometimes challenging nature trails in mountainous terrain, with both ascents and descents.
A good basic fitness level and some experience hiking in hilly areas are recommended.
Perfect for wildlife lovers, with opportunities to spot dolphins, seals, and birds.
Combines the adventure of sailing with tranquility, relaxation, and culinary indulgence on board.
No sailing experience needed – we’ll make sure you learn everything you need to help out on board!

Onboard Catering

Enjoy healthy, varied, and most importantly, delicious meals prepared with care by Mariëlle. Whether you’re vegetarian or have other dietary needs, we’ll make sure each meal is flavorful and made with fresh, local ingredients. Although we can’t offer vegan meals, we’re happy to accommodate other dietary requests. All meals on board are included, along with drinks like tea, coffee, milk, and orange juice. A glass of wine is served with dinner. Other drinks are not included and will be settled at the end of the trip. For safety reasons, no alcohol is served before or during sailing.

Lunches Ashore
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.

Discover the Flavors of Scotland During one evening of your 11-day voyage, our cook takes a well-deserved break, giving you the chance to immerse yourself in Scotland’s culinary delights. Join your fellow travelers for a shared dining experience or venture out on your own to explore a local restaurant. The exact evening will be planned during the trip, based on the itinerary and weather conditions. Please note that this meal is not included in the trip price and will be at your own expense.

Hands on Deck!

This adventure is all about rolling up your sleeves and joining the action! Whether you’re hoisting the sails, lending a hand in the galley, or simply sharing a laugh with your fellow sailors, your involvement makes life onboard lively and unforgettable. Together, we’ll create a warm, welcoming atmosphere where teamwork and fun go hand in hand.

Price

• €2,350,- (shared cabin)
• €3,525,- (single use of a double cabin, 50% surcharge)

Included:
• Captain and mate/cook
• All meals and drinks (tea, coffee, etc.)
• Use of Musto BR1 sailing gear, bedding, towels
• Eco-friendly showergel and shampoo
• And more!

Excluded:
• Personal expenses, soft drinks, and alcohol
• Travel to and from the ship
• Travel and cancellation insurance

Getting to the Ship

You are responsible for arranging your travel to and from the ship. There are daily flights to Glasgow, and from there you can take a train or bus to Oban, where our ship is docked. The journey offers breathtaking views of the Scottish countryside and takes about 4 hours.

We recommend planning your trip in advance and allowing enough time to arrive in Oban, so you can board the ship on time.

Click here for more info on how to get to Oban.

Book Your Trip with Steady Sailing

Ready to book your sailing adventure with Steady Sailing? Simply complete our booking form, and we’ll send you a no-obligation quote. Once you confirm, we’ll follow up with a few additional questions and finalize your booking. This ensures we’ve got everything covered for your unforgettable journey along Scotland’s west coast and the Hebrides.

For questions or to book, click here – we’re happy to help!

Travel & Cancellation Insurance

We highly recommend that you secure your own travel and cancellation insurance for your sailing trip. This will ensure you’re prepared for any unexpected situations. Please make sure your insurance covers both the trip and the activities you plan to do with us.