• Wave icon Trip Type: Coastal
  • Speech bubble icon Instructors: 2
  • People icon Crew Size: Max 9 (10 for ocean)
  • Cake icon Ages: 18-70 ish
  • Pin icon Region: UK & Ireland

Adventure Rating:

Low to some

Experience Required:
Low to some

12 Days from £1,899

Dates, Prices & Travel

Sailing in Scotland, Orkney, Fair Isle, & Shetland

The Wild Islands sailing adventure is a captivating sail through Scotland’s most remote and beautiful archipelagos – the Hebrides, Orkney, Fair Isle, and Shetland, the latter islands also being known as the Northern Isles. Discover the rugged charm of these wild, windswept islands from the unique vantage point of the sea. Make landfall to explore the mystical standing stones of Orkney, the unparalleled natural beauty of the Hebrides, the rich birdlife of Fair Isle, and Shetland’s stark, dramatic landscapes. Navigate through enchanting, secluded bays surrounded by wildlife and historic sites. The Wild Islands is your chance to sail and explore these islands in all their magical glory.

Ready for the trip of a lifetime with Europe’s #1-rated adventure sailors?

Rubicon 3 expeditions are genuine sailing adventures. Depending on your chosen route, you will be off the beaten track, possibly out on the open ocean, sailing to and exploring remote and beautiful places. The expert Rubicon 3 instructors will train you and ensure you are fully involved in all aspects of the experience, including navigating, helming, trimming sails, cooking, and looking after the yacht. As a true sailing adventure, it is much less predictable (& much better!) than a packaged experience, with itineraries planned day by day and shaped by local circumstances and weather. To participate in the adventure, all we ask is that crew have an appetite for adventure, an open mind, and a desire to be fully involved.

Want to join?

Go to the Dates & Prices button to see this trip’s dates. It will also give you information on connecting travel, including where to fly and when and where to join the boat.


Sailing Area

scotlands wild islands area map for sailing
scotlands sailing map for wild islands route
The Yachts
Key Information
What’s included
  • All food and accommodation on board

  • All fuel & berthing fees

  • Your own bunk and storage area

  • Use of oilskins

  • Use of lifejacket

  • Sailing tuition

  • RYA Competent Crew (supplementary fee)

What’s Not included
  • Your connecting travel to & from boat

  • Sailing & travel insurance

  • Meals you choose to eat ashore

  • Alcohol

  • Visas where required

  • Discretionary tip

Interested in dates & availability?

To see when this trip runs, its start and end locations, price to join the crew and availability, click on the ‘Dates, Prices & Travel’ button up top.

Discretionary tipping of the Rubicon 3 crew

The trip price is 5% less than we would normally charge. This is to allow you at the end of your adventure to offer a combined 5-10% tip to the Rubicon 3 skipper and mate if you feel they have delivered exceptional performance. This tip is entirely discretionary. See our FAQs here.

Got some questions?

Joining a big sailing adventure is a big thing, so don’t be surprised if you have lots of questions before you book. Who else joins, what to expect, and so many more queries are entirely normal. The home page has loads of info on this (scroll to the bottom), there are our FAQs and never hesitate to contact us by email, phone or live chat. The team are here to have a chat, discuss options, answer questions and help make sure you get on the exact right sailing trip for you.

Welcome to Scotland and the wild and spectacular islands off its west and north coasts. This 12-day sailing itinerary takes you on a thrilling journey through the stunning landscapes and seascapes of the Outer Hebrides, Orkney, Fair Isle, and Shetland. The wind and the weather at the time dictate where we can go and when. Here are some of the highlights that are possible.


The Wild Islands begins and ends in Stornoway, the jewel of Scotland’s Outer Hebrides. The bustling port town is a captivating blend of history and natural beauty and is renowned for its maritime heritage. It has been the epicenter of Hebridean life since the early 19th century, and the historic Lews Castle overlooks a harbor teeming with life.

castle on lewis

Handa Wildlife Reserve

Handa is home to one of the largest seabird breeding colonies in Europe. The island’s beautiful cliffs rise vertically out of the sea and are home to over 100,000 breeding seabirds, including guillemots and razorbills. You will also likely see marauding Skuas, Kittiwakes, Fulmars, and Puffins. From the cliffs, there are spectacular views north to Cape Wrath and south to the point of Stoer. The island has rich and varied plant life and is also an excellent location to spot cetaceans such as the common dolphin, Risso’s dolphin, minke whale, and basking sharks.



Passage to Orkney

It’s a wonderful 70-80 mile sail around the very top of Scotland to the Orkney islands. You’ll round Cape Wrath into the North Sea and sail east toward the Pentland Firth and Orkney. Depending on the weather, it is a long day of sailing, so expect a start at dawn as the Sun creeps over the horizon and a late afternoon finish in time for Fish and Chips in town!

yacht hummingbird



Orkney is a mesmerizing blend of ancient history and breathtaking natural landscapes. This UNESCO World Heritage Site is home to some of Europe’s most well-preserved Neolithic sites, including the mystical Ring of Brodgar and the ancient village of Skara Brae, giving a glimpse into life over 5,000 years ago. Orkney has an incredible history, from these enigmatic stone circles to the remnants of World War I and II, seen in the Churchill Barriers and the haunting Italian Chapel, a symbol of hope built by prisoners of war. The islands are rich in wildlife, with rugged coastlines and a real natural beauty, from dramatic cliffs to serene beaches.


Fair Isle

60 miles northeast of Orney is the remote island of Fair Isle. Sometimes, the weather will not allow us to stop here, but it is a beautiful goal to aim for. The island is a world-famous location for birdwatchers and nature enthusiasts, being a pivotal point for migratory birds. Fair Isle is also famed for its distinctive hand-knitted sweaters, a tradition that dates back centuries. Surrounded by spectacular cliffs and the open sea, Fair Isle’s isolation has preserved a way of life that offers a rare glimpse into a more spartan, connected existence.

fair isle


Another 40 miles northeast are the most rugged and wild Isands of all – the Shetland Islands, where we can spend a few days exploring. Just 150 miles southeast of the Faroe Islands, Shetland is a subarctic archipelago of Scotland and a land of stark, wild beauty with rich Norse heritage. Located at the crossroads of the Atlantic and the North Sea, it has a unique cultural tapestry woven from Scottish and Scandinavian influences. Shetland is renowned for its coastline, with over a hundred islands, each offering dramatic cliffs, remote beaches, and abundant wildlife. The islands are steeped in history, from ancient Pictish ruins to the Viking legacy evident in the annual Up Helly Aa festival, which celebrates Shetland’s Viking past with fire and festivity. We will likely finish the adventure with one overnight sail back to Stornoway, giving us a magical night under the stars, sailing in a watch system, and making memories for life.

shetland ox

A brief overview of the sealife you might encounter on this itinerary:

  • Scallops: You’ll find some of the best scallops in Scotland around the waters of Scalpay, a small island in the Outer Hebrides. These delicious shellfish are often served in local restaurants and are a must-try for seafood lovers.
  • Whales and Dolphins: The waters around the Outer Hebrides and the Shetland Isles, in particular, are home to various whale and dolphin species, including killer whales, humpback whales, minke whales, and Risso’s dolphins. Watch for these majestic creatures as you sail through the region.
  • Seals: The coasts of Scotland are home to several species of seals, including grey and common seals. You can often see them basking on rocks or swimming in the water.
  • Birds: The islands of Orkney and Fair Isle are important breeding grounds for many bird species, including puffins, guillemots, razorbills, and fulmars. You can also spot a variety of seabirds, such as gannets and kittiwakes, as you sail along the coast.
  • Fish: The waters around Scotland are teeming with fish, including Atlantic salmon, cod, herring, and mackerel. You might also spot less common species, such as anglerfish or monkfish.

Dates, Prices & Travel

Start Date & Location

August 5, 2024

End Date & Location

August 16, 2024





Trip Information

Start Date: August 5, 2024

Start Time: 09:00

Start Country: Scotland

Start Port: Stornoway

Start Marina: Stornoway Marina

End Date: August 16, 2024

End Time: 10:00

End Country: Scotland

End Port: Stornoway

End Marina: Stornoway Marina

Find Flights For This Trip
Fly Into: Stornoway Airport (IATA Code: SYY)
Fly Out of: Stornoway Airport (IATA Code: SYY)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Stornoway, Scotland.
  • It is scheduled to be in Stornoway Marina.
  • You can get to Stornoway via Inverness (details here), from Edinburgh (details here) or from Glasgow (details here)
  • The trip starts at 9:00 AM on August 05 2024, so you will need to be in Stornoway by August 04, 2024.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in Stornoway.
    • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in Stornoway, Scotland
  • The boat is scheduled to arrive into Stornoway on the evening of August 15th, 2024, and you will need to disembark by 09:00 AM, August 16th, 2024.
General Notes
  • We have a very strong track record of meeting the scheduled end date, with only a few exceptions over a decade of sailing and across hundreds of thousands of miles of sailing. However, given the nature and distance of ocean crossings, we can’t guarantee it and recommend booking flexible onward travel or at least allowing an extra day in your itinerary as a precaution.
  • You cannot stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.
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