Join our mailing list

Help me choose!

Adventure sailing holiday in Scotland’s Wild Islands

Adventure sailing holiday in Scotland’s Wild Islands

Coastal Sailing

No previous experience required

Come alone or in a group

Come sail and explore the magnificent islands of the Hebrides, Orkney, Fair Isle and the Shetlands. These are the most northern outposts of Great Britain and are rich with wildlife, culture and a rugged beauty that is hard to match. They are actually a collection of over a hundred islands, with Orkney having 70 itself. For all the wind and weather, the islands are close to each other meaning short distances to sail and they have superb bays and beautiful, deserted anchorages that give excellent shelter. Between Orkney and Shetland lies tiny Fair Isle. You may only have heard about it from the shipping forecast but it had a small community, thousands of birds and is a fascinating place to explore.

Sailing location image
Route Map Image

These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: August 08 2021. Oban, UK
  • End date / place: August 21 2021. Stornoway, UK
  • Full price: £1,899
  • Deposit: £760


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



This is 40% of the trip price and is non-refundable. On making payment, your berth is guaranteed.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.

This is a typical itinerary for the Wild Islands from Oban to Inverness. Your start and endpoints may differ, but the trip remains much the same. What makes an adventure holiday so special however is that there can be no fixed itinerary. The wind and the weather ultimately shape what’s possible each day and where we go!

Joining day

Join the boat and get your belongings packed away and relax. There’s plenty of things to do in the future but right now it’s about relaxing, finding your way around the boat and enjoying the surroundings. After lunch, we’ll start to show you the boat, issue lifejackets and oilskins and teach you the most important skills when on board.

Time to learn the ropes

Today is all about getting up to speed with the boat. Whether you are a complete novice or more experienced sailor, everyone benefits from detailed introductions, safety briefings and training sessions. You will have two highly experienced instructors to guide you through every aspect that you need to know to have a great sailing holiday. By lunchtime we should be casting off the lines, hoisting the sails and working through all the key sailing manoeuvres such as tacking and gybing, reefing and knot tying!  Tonight we’ll likely stop in the gorgeous harbour of Tobermory on the Isle of Mull

Passage to NW Skye

Today we have the lovely 60nm sail to the north-west corner of Skye.  It is thought that the origins of the name go back to the Viking words Ski (cloud) and Ey (island). In Gaelic it is called An t-Eilean Sgitheanach, which translates as The Winged Isle, thought to be named after the shape of the top of Skye where the peninsula’s of Trotternish and Waternish look like wings. It is also referred to as The Misty Isle (in Gaelic – Eilean a’ Cheo). As we sail up north, we leave the isle of Rum to port and work our way up the beautiful west coast of Skye. Here we have Lochs Dunvegan and Snizort where if we make good time we can go ashore and visit Dunvegan Castle.

The Hebrides

A lovely shorter sail of about 25nm now awaits us. After we weigh anchor and leave Skye behind, we will navigate our way up through the little Minch and along the east coast of the Hebridean isle of Harris. Although there are so many wild and wonderful anchorages to choose from, the Shiant Islands are a real win and if the weather allows us to anchor there, you will be in for a real treat. They are one of the great bird-stations of the northern hemisphere, with some 300,000 seabirds, including puffins, guillemots, razorbills, shags and great skuas, arriving there in the summer to breed. They are a wild and beautiful place to visit.

Passage to Orkney

Now we have a really exciting passage, with about 120nm to get to Orkney. We’ll leave Stornoway to port and head up through the North Minch until we get to the infamously named Cape Wrath and the most north-westerly point in mainland Britain. There’s no time for us to stop though, so we must admire its towering cliffs from afar and turn east and toward the Isle of Hoy. We will be sailing right through the night, so we can hope to see a wonderful sunrise as the Orkneys come into view and landfall will be an extra special experience.

We will have time now to explore ashore and there are the Neolithic stones, bronze age huts and wildlife, cliffs and views that you will never forget. There is a real sense of timelessness here, knowing that it is all much as it was for our fore-fathers hundreds or thousands of years before us. Visits to archaeological sites at Maes Howe, Skara Brae, and the towns of Kirkwall and Stromness are a must when visiting here.

One of the highlights here is Scapa Flow, where the German navy was scuttled after the first world war. While we do not have time to dive on it, it is a beautiful and historic area and has some wonderful anchorages where we can spend the night and reflect on the extraordinary history of the area.

The elusive Fair Isle

If the weather is kind to us, we will next be able to sail to the wonderfully remote Fair Isle, of British maritime forecast fame. Marooned halfway between the Shetland and Orkney archipelagos, Fair Isle is one of Britain’s most remote inhabited islands. Raised by precipitous cliffs out of a sea that has claimed dozens of shipwrecks, the island can feel like the very edge of the worlds. It has two very small harbours which are not always calm enough to enter, but if we are lucky it is a really lovely place to stop for the night.

Shetland Isles

Only another 20nm northeast from Fair Isle, Shetland is a spectacular place to sail and explore. It is actually an archipelago of more than 100 islands and has huge dramatic cliffs and wonderful, sheltered harbours. The Shetlands are a nature lovers paradise and you can hope to see puffins, kittiwakes, fulmars and guillemots on the cliffs and dolphins, minke whales and orca in the sea. Everywhere we stop, you’ll find many Otters, common and grey seals and harbour porpoises in full view.

Shetland also has a wonderful live music scene and when we visit the pubs in town, there is often a fiddle playing, maybe a piano and as the night goes on, an increasingly lubricated song from the locals!

The islands are a Unesco geopark and despite their proximity to Norway are uniquely Scottish, with deep glens flanked by steep hills, beautiful lochs and, of course, sheep everywhere!

Passage to Inverness

It’s time to start heading south again, and it’s about 180nm to Inverness, so we can’t hang around, hard though it is to leave. There’s still some very special sailing to be done, and we’ll likely head to Kirkwall in the Orkneys to revictual and break up the passage. From there, it’s another long day sail up the famous Moray Firth with its incredible dolphins and porpoise and into the wonderful Scottish town of Inverness.

Debrief, clean up and goodbyes

It’s always amazing how quickly everyone has become firm friends, and the boat and its routines seem so familiar. Yet it’s time to wrap it all up and head home. We’ll get the boat back to how we found it, sign logbooks, exchange emails and disembark by 1200hrs.


  • You should join the boat at 1100hrs on the start day. It is important you are not late.
  • You will disembark between 0700 and 1200hrs on the end day.
  • For the exact start and end locations, please see the ‘Dates & Prices’ tab



    • A Rubicon 3 coach will run between Glasgow railway station and Oban marina at 0800 on the start / end date. It is scheduled to arrive by 1100hrs. Tickets are £30 and can be booked here.


    • Stornoway airport (IATA code: SYY)  is served by direct flights from the mainland (all less than about an hour’s duration) from Aberdeen, Edinburgh, Glasgow and Inverness.  Flights are by Flybe and Eastern Airways.
    • Caledonian MacBrayne ferries sail at least twice daily in each direction between Ullapool and Stornoway (one each-way crossing on Sundays).
    • Scottish Citylink coaches operate service number 961 (booking essential) from Ullapool to Inverness (& v-a-v), with luggage handling through to Stornoway arrivals hall.  Citylink connects with coach services from Glasgow and Edinburgh, which in turn connect with the National Express network.


    • Stagecoach operates the Jet Bus Service to Inverness Airport with up to a 30 minute service between the City of Inverness and the Airport.
    • Inverness Train Station is about a fifteen minute taxi ride away from the airport and onward links are available to many destinations within the Highlands as well as Aberdeen, Glasgow and Edinburgh. If travelling by bus from Inverness airport, passengers should get off at Academy Street by the Eastgate Shopping Centre to access the train station.


    These adventure sailing holidays are open to anyone aged 18 – 70 years. No previous sailing experience is required for this route


    We provide the foul weather clothing, life-jackets and all other technical equipment you will need. You need to bring a sleeping bag and some waterproof boots.

    See more information and the full kit list here


    We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

    Fitness to sail


    Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

    See the Medical Declaration here


    • All crew must have adequate travel insurance in place for your sailing holiday.
    • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim you fees.
    • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
    • For our latest guidance on travel insurance, please read here.


    For a full explanation of what to expect with the various trip ratings please click here.


    • Oilskins
    • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
    • Ocean-spec lifejackets. These are the best on the market.
    • All on-board food and snacks.
    • Daily sailing lessons and tuition from two highly experienced instructors.
    • RYA sailing qualifications where applicable.


    • Your travel to and from the start and end points.
    • Travel insurance (see our travel insurance page here)
    • Any alcohol – but feel free to bring your own or buy some along the route.
    • Any meals you eat ashore.


    Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

    • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
    • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy.
    • When you book, the deposit is non refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
    • Please ensure you have read and agreed to the T&Cs and Trip Notes before booking.