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27-09 Outer Hebrides Challenge: Adventure & Offshore Experience

26-June-2027 - 06-July-2027 - 11 days
Available: (8/8)

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27-09 Outer Hebrides Challenge: Offshore Avontuur  - Steady Sailing

Tour Overview

In June, the days in the Hebrides are long, with almost endless daylight. This gives us the time to sail further, explore new places and fully immerse ourselves in life on board.

During this journey along the rugged west coast of the Outer Hebrides, we set sail early, take advantage of calm tides and only drop anchor as the sun slowly sets. Sailing itself is already an experience: peaceful, vast and deeply connected to nature.

We depart from Oban and make challenging offshore passages to the Outer Hebrides and the remote Monach Islands. This trip is ideal for sailors who want to build miles, expand their offshore experience and improve their navigation and sailing skills.

The route depends on the weather, making flexibility, teamwork and perseverance essential. Along the way you will experience spectacular landscapes, unique wildlife and quiet anchorages – a truly unforgettable experience.

On board you will be actively involved: steering the yacht, hoisting sails, planning passages, navigating and standing (night) watch – all under the guidance of an experienced skipper.

Exclusive youth discount: 15% discount for participants up to 29 years old!

  • Skippered sailing
  • Sheltered waters
  • Private cabins
  • Great for couples & solo travellers
  • Full board
  • Wildlife watching

Depature & Arrival Details

Available 8/8
Depature From Oban
Depature Time 26 June 2027 at 17:00
Arrival to Ullapool
Arrival Time 6 July 2027 at 10:00
Travel Time 11 Days
About the sailing trip

Highlights of this trip:

  • Challenging crossing to the Hebrides – Experience the ultimate feeling of open-water sailing
  • Long sailing days – Sail across vast seas and enjoy spectacular coastal landscapes
  • Meet the wildlife – Spot puffins, auks, dolphins, seals and sometimes even orcas
  • The Shiant Islands – Discover impressive seabird colonies and untouched cliffs; land by dinghy for exploration ashore
  • Stornoway & Lewis – Walk through the harbour town of Stornoway and enjoy the charming streets and local atmosphere

Day-to-day programme – Possible itinerary

Day 1 – Welcome in Oban

  • Welcome on board at 17:00, followed by dinner
  • Introduction to the ship, safety briefing and overview of the trip
  • Overnight on board

Day 2 – Oban to Tobermory (Mull)
In the morning we start with instruction on rigging and ship handling. We set course northwards through the Sound of Mull towards the colourful harbour of Tobermory. A perfect first day to get used to the watch system, handling the sails and life at sea.

  • Overnight in Tobermory

Day 3 – Tobermory to Barra
A longer offshore stage across the Sea of the Hebrides. Prepare for open-water sailing and the chance to spot dolphins and seabirds along the way. We arrive in the beautiful bay of Barra, known for its white beaches and rugged landscapes.

  • Overnight at anchor

Day 4 – Exploration of South Uist
We set course north towards South Uist, along the rugged coastline. In good weather there is time to go ashore and explore parts of this remote island.

  • Overnight near South Uist

Day 5 – North Uist & the Sound of Harris
Today we sail towards North Uist, one of the most spectacular and challenging areas of the Hebrides. The passages between the islands offer excellent opportunities to practice navigation skills.

  • Overnight near North Uist

Day 6 – The remote Monach Islands
A highlight of the trip: the wild, uninhabited Monach Islands. Known for wide beaches, seabirds and grey seals, this place truly feels “off the map”. Weather and sea conditions determine whether we can go ashore.

  • Overnight at anchor

Day 7 – West coast of Lewis
We sail north towards the dramatic Atlantic coast of Lewis. Expect impressive landscapes, open water and great opportunities to log miles and gain offshore experience.

  • Overnight on the west side of Lewis

Day 8 – Sailing to the Shiant Islands
We continue towards the mysterious Shiant Islands, home to thousands of seabirds and impressive basalt cliffs. In favourable conditions we explore the islands by dinghy and enjoy their wild beauty.

  • Overnight at anchor near the Shiants

Day 9 – Shiant Islands to Stornoway
A shorter sailing leg brings us to Stornoway, the cultural heart of Lewis. Time to stretch your legs, explore the town or simply enjoy a warm shower and rest after the offshore miles.

  • Overnight in Stornoway

Day 10 – Final leg to Ullapool
Our final sailing day takes us across the Minch towards Ullapool, surrounded by mountains and rugged coastline. We end the trip with a final dinner and celebratory moments ashore.

  • Overnight on board in Ullapool

Day 11 – Disembarkation in Ullapool
Disembarkation at 09:00, with new sailing miles, more confidence and unforgettable memories of the Outer Hebrides.

Nature sets the course: Nature and weather play an important role in our sailing trips, making each journey unique. The proposed route serves as inspiration and may be adjusted depending on conditions, always prioritising safety and enjoyment.

Wildlife

Sailing with Steady is often rewarded with impressive wildlife encounters. Seabirds such as puffins, skimmers and guillemots are often seen in large numbers, while sea eagles soar majestically along the rugged coastline. On land you may spot impressive red deer, and with a bit of luck even an otter in the bay. The surrounding soundscape is magnificently overwhelming, with the calls of seabird colonies echoing against the cliffs, especially during the breeding season. Puffins, razorbills and guillemots add their distinctive calls to the scene. While sailing through Scottish waters you may also see seals curiously lifting their heads above the surface. The Scottish coasts host many seals and it is not uncommon to see them resting on rocks or sandbanks in the sun.

Dolphins are frequent visitors: common dolphins, bottlenose dolphins and white-beaked dolphins are often spotted, and occasionally Risso’s dolphins or Atlantic white-sided dolphins appear. Whales, including minke whales, are regularly seen. Sometimes humpback whales appear, but the real star is the local group of orcas – an unforgettable experience if you see them. Keep your binoculars ready and enjoy the spectacle!

Practical information & suitability

Do you love adventure, nature and good company? Then this trip is exactly what you are looking for! Whether you are an experienced sailor or setting sail for the first time — everyone is welcome. This journey is ideal for those who enjoy being active, discovering new places and experiencing the outdoors in great company.

Our trips in Scotland are suitable for travellers aged 16 to 75 years who:

  • enjoy variety and new experiences;
  • like travelling in a small, friendly group;
  • want to be active but also relax;
  • regardless of experience, both beginners and experienced sailors who want to help out and learn along the way.

On board, you will learn everything you need to actively participate in sailing — at your own pace.


Mobility and Safety on Board

Life on board requires a certain level of agility. You need to be able to move independently through narrow spaces, over stairs and high thresholds. For your own safety and comfort, it is important that you:

  • can move safely on a moving vessel, both on deck and below deck;
  • can pass through narrow spaces (minimum 60 cm wide) and use stairs.
For Walking and Traveling – For Active Walkers

Our hikes are ideal for active walkers. Routes vary in length from 10 to 18 km and offer varied landscapes with both climbs and descents. Occasionally you will encounter steeper sections, but the hikes remain manageable for those in reasonable physical condition. The routes may take you over rugged rocky paths or through wet grassy terrain. Because the landscape can sometimes be unpredictable, it is important to be well prepared. Therefore, when booking we provide a packing list with everything you should bring in your day backpack.

These hikes are for those who enjoy a light challenge and love experiencing nature in its purest form, along rugged and often untouched trails. Jan-Willem and Mariëlle guide the hikes so that we can discover the most beautiful places together as a group.

Life on board

Steady has been sailing in Scotland for over 10 years with the Dutch husband-and-wife team Jan-Willem and Marielle. Their love for Scotland, sailing and the natural world is clear for guests to see, and they are well versed in all the hidden gems and secret spots.

Getting involved

Steady lives up to her name with a simple rig and an easy-to-use winch system, making her a great platform for guests to learn the ropes. Jan-Willem and Marielle can sail Steady comfortably on their own, but they actively invite and encourage guests to take part in all aspects of sailing. From taking the helm and setting the sails to basic navigation and rope work, everything is done in a safe and supportive environment.

A typical day

After a hearty breakfast, the sails are set with the aim (weather permitting, of course) to sail for 4 to 7 hours. A secluded anchorage is then found, away from the tourist hustle and bustle, to settle in for the night. Lunch is served either under sail or at anchor, freshly prepared by Jan-Willem and Marielle in the spacious galley.

In the afternoon there is time to explore ashore before enjoying a delicious freshly prepared dinner on board, sharing sea-faring stories and stargazing from the deck.

Sleeping and relaxation

The main deck is well designed with plenty of open space and a cockpit ideal for alfresco dining. The covered deckhouse features 360-degree windows, perfect for morning coffee while watching the sunrise or for shelter when the Scottish weather changes.

Below deck you will find a beautifully appointed galley and a generous, comfortable saloon, recently refitted to a high standard. Forward along a small corridor are four well-designed twin bunk cabins, with a toilet and a separate shower for guests. The crew quarters are located in the stern.

What’s included

As with all Steady sailing holidays, your ticket price includes breakfast, lunch, dinner, snacks and hot drinks. Soft drinks and alcoholic beverages can be purchased on board. Single occupancy is available with a 50% surcharge. All cabins are provided with bedding and towels. There is a suggested age limit on Steady’s trips; if you are over 75 years old and interested in sailing with Steady, please contact our office.

Catering on board

Enjoy healthy, varied and above all delicious meals on board, carefully prepared by Mariëlle. Whether you prefer vegetarian meals or have other dietary requirements, we make sure every meal can be enjoyed with fresh and local ingredients.

Unfortunately, we cannot offer vegan meals, but we are happy to accommodate other dietary wishes. All meals on board are included in the price, along with drinks such as tea, coffee, milk and orange juice. A glass of wine is served with dinner.

For safety reasons, alcohol is not served before or during sailing. Additional drinks are not included and will be settled at the end of the voyage.

Boat info

Guest berths: 8   Rig: Staysail Ketch

Onboard Steady, most guests like to lend a hand with the sailing, and Jan-Willem and Mariëlle are excellent guides if you do want to get involved. They cater for all abilities and ages, so if you’d rather sit back and relax with a book, then that’s fine too. She has a modern rig and a simple winch system, so she is a great boat to learn the ropes.

Steady’s voyages explore the islands of the Inner and Outer Hebrides and St Kilda; an area of unspoilt wilderness and breathtaking beauty in the Western Isles of Scotland. Her sailing adventures give you access to the most captivating and remote hidden secrets of this incredible place. As you sail through this stunning marine landscape, you may be lucky enough to encounter rare wildlife up close and have time to soak up the unique history and culture of the Hebrides and St Kilda.

Steady is true to her name, with a sturdy steel hull, and was initially built as a charter vessel, offering a considered layout below decks. Fitted with all the mod-cons and keeping guests’ comfort at the forefront, she sleeps eight guests in four comfortable twin cabins, with a shared shower and a separate toilet. The galley and saloon sit at the heart of the boat, featuring a peninsula galley and plenty of seating alongside the cosy multi-fuel stove.

On deck, there’s a spacious cockpit with a navigation station and additional seating—perfect for breakfast and morning coffee as the sun rises. There’s plenty of room on deck too, to take in the surrounding views and learn the ropes alongside Jan-Willem and Mariëlle, who love sharing their passion for Scotland, the environment and nature with their guests.

Deck plan

Deck plan of sailing vessel Steady showing the deck-level cockpit, central saloon and galley, four twin guest cabins, separate shower and toilet, and crew quarters in the stern.
What’s included
  • All meals are included in the price (breakfast, lunch, dinner and hot drinks)
  • All bedding (pillow, sheets and duvet) and a wash towel
  • Full crew plus tuition
  • Walking guides
  • Marina and fuel fees
  • All tender trips to and from the boat
  • Lifejacket
  • Musto sailing waterproof suits whilst on board (standard sizing)

What’s not included

  • Alcohol and soft drinks
  • Any flights
  • Transit hotels
  • Travel to and from the boat on the day of joining and leaving
  • Travel insurance
  • Sailing insurance (please read our Sailing Insurance page for more information)
  • Crew tips
  • Personal expenses

Travel insurance notes

As this is an active adventure holiday, we advise that everyone has appropriate personal accident travel insurance while on board, in addition to standard travel insurance that covers the period between booking and departure. These policies can sometimes be combined, so please check with your travel insurance provider.

Please read more information on our Insurance Guidelines page.

Kit list

Steady has limited space for personal belongings, so please be considerate and travel as light as possible. There is no storage for rigid cases; please bring your items in a soft bag.

We recommend travelling light with plenty of lightweight, quick-drying layers. Below is a list of suggested items. These are not mandatory, and those with sailing experience may have their own preferences.

  • Fingerless gloves for hoisting sails (sailing or cycling gloves work best)
  • Walking boots or shoes for onshore use, plus light shoes or trainers with good grip
  • Wash towel – microfibre is lightweight and quick-drying
  • Swimsuit and swim towel
  • Lightweight, quick-dry clothing (base layers, fleece and synthetic tops)

It can be several degrees colder out at sea, so please bring plenty of layers even if the forecast suggests a warm week.

  • Warm, windproof and waterproof jacket and trousers (some offshore MUSTO waterproof sailing jackets and trousers are available for guest use on board; these must remain on the boat and availability is limited, so please let us know if required)
  • Waterproof boots or clean Wellington boots
  • Sun cream (please use reef-safe, eco-friendly products where possible)
  • Smidge insect repellent
  • Sunglasses and a warm hat or cap
  • Small personal first aid kit and any medication you may need
  • Camera and/or binoculars
  • Refillable water bottle
  • Personal wash kit (please use reef-safe, eco-friendly products where possible)
  • Charging cables for personal devices (12V USB sockets are available on board)
  • A good book to read
  • We recommend sleep masks and/or earplugs
Important Information – ETA & Guarantee

Important information: ETA required for travel to Scotland from 5 March 2025

From 5 March 2025, an Electronic Travel Authorisation (ETA) will be required for travellers to the United Kingdom, including Scotland.

What you need to know

  • An ETA is a digital travel authorisation required for your journey. Without an ETA you cannot enter the UK.
  • The application costs £19 and is usually processed within 3 working days.
  • Your ETA is valid for 2 years or until your passport expires.

How to apply for an ETA

You can easily apply for your ETA via the official UK government website:
www.gov.uk/get-an-eta

Please make sure to arrange this in time so you can fully enjoy your sailing trip. If you have any questions, feel free to contact us.

Guarantee scheme

This offer is covered by the STO Garant guarantee scheme. The terms and conditions can be found on the STO Garant website:
www.sto-garant.nl/downloads

Price
€ 2500 / Person
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Fantastic sailing experience with Steady Sailing from Medemblik to Dover!
I can't stress enough how fantastic my experience with Steady Sailing was on my recent voyage from Medemblik to Dover. From the moment I stepped aboard, I felt welcomed and cared for by my hosts, Mariëlle and Jan-Willem.
Gert-Jan Turnhout