Z02-27: Fair Isle Expedition | Sailing Voyage to Scotland’s Most Remote Islands (Orkney, Fair Isle & Shetland)

One of our most remarkable sailing voyages.

This journey takes us through the remote island worlds of Orkney, Fair Isle and Shetland, a region of dramatic sea cliffs, vast seabird colonies, ancient archaeological sites and small island communities. It is a voyage for nature lovers, walkers and those seeking peace and quiet in some of the most unspoilt corners of Europe.

Orkney: Dramatic Cliffs and Ancient History

We begin in Stromness and first set sail for Hoy, the wildest of the Orkney Islands. Here we enjoy a spectacular walk to the famous Old Man of Hoy, a 137-metre sandstone sea stack that has become one of Scotland’s most iconic natural landmarks. Towering cliffs, Atlantic swells and sweeping coastal views make this one of the highlights of the voyage.

In the evening, we continue to a small island near the entrance to Scapa Flow, where we can enjoy the tranquillity, wildlife and views across one of the world’s largest natural harbours.

Our next destination is Rousay. Along the way, we pass impressive cliffs and rolling green hills that are characteristic of Orkney. The almost treeless landscape gives the islands a unique and timeless character. Rousay is often referred to as the “Egypt of the North” due to its remarkable concentration of Neolithic and Bronze Age archaeological sites. It is also home to the remains of a once-grand country house and its surprisingly beautiful botanical garden, an unexpected sight on these remote islands.

Via the historic town of Kirkwall, the capital of Orkney, we may visit another island before setting course for the true highlight of the voyage: Fair Isle.

Fair Isle: A Paradise for Birdwatchers

Situated halfway between Orkney and Shetland, Fair Isle is one of Europe’s most remote inhabited islands. Only a few dozen people live here year-round. There are no crowds, no busy roads and very few visitors. This sense of isolation is exactly what makes the island so special.

We spend two days on Fair Isle, giving us plenty of time to explore on foot. The island’s spectacular cliffs are among the highest in Britain and provide nesting sites for thousands of seabirds. Puffins, skuas, guillemots, razorbills and many other species breed here in large numbers. In the evening, it is often possible to watch hundreds of puffins returning from the sea to their burrows high above the cliffs. With so few visitors, these remarkable birds can often be observed from surprisingly close range.

The Fair Isle Bird Observatory is also well worth a visit. From its welcoming café, we enjoy views over the harbour, where seals are frequently seen resting on the rocks below. For birdwatchers, Fair Isle is considered one of Europe’s premier wildlife destinations.

Shetland: Seabird Cliffs and Viking History

After Fair Isle, we continue north to the Shetland Islands. If conditions allow, we visit Sumburgh at the southern tip of the archipelago. Here, dramatic cliffs and seabird colonies are accompanied by fascinating archaeological remains, including evidence of both Pictish and Viking settlements.

Our voyage concludes in the lively harbour town of Lerwick, Shetland’s capital. After a beautiful approach through the islands, we celebrate the end of the voyage with a meal together ashore.

A Sailing Voyage for Active Nature Lovers

Daily sailing distances during this voyage typically range between 15 and 40 nautical miles, leaving plenty of time for walks, wildlife watching and exploring ashore.

This sailing voyage is ideal for active travellers, nature lovers and anyone seeking a slower pace of life. The combination of remote islands, spectacular coastal scenery, abundant wildlife and relaxed sailing days makes it one of the skipper’s personal favourite voyages – and for many guests, a destination unlike anywhere else in Europe.

The itinerary described above is dependent on weather, wind and tidal conditions. If necessary, the route may be adjusted accordingly.

Read more about our Sailing holidays to the Orkney and Shetland islands

Information about this sailing holiday

Participants of this sailing holiday

Book your sailing holiday

Sailing holidays Prices 

The price is the rental cost for the ship with crew, including food and drinks on board, hence full board. The price mentioned is per person.

Included in the price:

– Food and drinks on board.
– Fuel, water, shore power, harbour fees and tourist tax.
– 1 towel set and bedding incl. duvet and, of course, a life jacket.
– For after sailing there is also wine and beer on board, based on average use. Should we run out, then you can purchase more yourself.

Not included:

– Your transfer, meaning your journey to and from the ship
– Sailing clothes and boots, you can rent these from us if you would like.
– Possible shore excursions such as renting a van, or visiting a museum etc.
– Food and drinks ashore, the last evening we will go out for dinner and this will be at your own expense. ( Should you wish to treat the crew as a thank you for a lovely sailing holiday, it would of course be greatly appreciated!)
– Optional tips. These are, of course, entirely voluntary, but always appreciated. Any tips are shared between the skipper and crew, because the skipper is just as much a part of the team that makes the voyage possible. Contrary to what many guests assume, the Bosun/cook on board Cherokee is actually the highest-paid member of the crew.

Duration & Time on Board

The listed trip duration refers to full calendar days. Since you embark on the first evening and disembark on the final morning, your actual time on board is on average about 1.5 days shorter. We use this format to keep our trips comparable with other providers – but we like to be transparent about the real time you’ll spend on board.

Sailing holidays discount

Customer Discount:
If you book a second sailing holiday with us within a year, you’ll get 2.5% off the ‘board price’.

Sailing holidays group discount:
If you book a sailing holiday as a group (more than 3 passengers), you will receive 2.5% discount per person on the ‘board price’.

Sailing holidays youth Discount:
If you are under 29 years old, you will get 5% discount on the ‘board price’.

Sailing holidays discounts can not be combined with each other.

Bonus Discount:
€25 extra discount when you choose a vegetarian menu on board.

Private charter

You can also rent the ship and crew for a privat charter. Then multiply the price with 7. For a private charter, you can choose one of the offered sailing holidays, provided there are no other bookings for that sailing journey. If you would like more information on private charter, please contact us.

Sailing holidays with your own private cabin

If you are a solo traveler and would like the comfort of a private cabin (room), you can reserve it for 1.6 times the price (for crossings, it will be 1.9x).

Extend your sailing holidays with an extra day B&B

On some of our sailing holidays, it is possible to book an extra overnight stay on board based on Bed & Breakfast (B&B, so without dinner) for € 125 per person. This automatically applies when booking multiple trips in a row.

Sailing holiday categories

Category A:
Offshore crossings, includes also sailing throughout the nights. Passengers will also be grouped in the watch system.

Category B:
Offshore sailing holidays, there will be no sailing throughout the nights, but occasionally a late arrival at the harbour (or an early departure), depending on the weather.

Category C:
Relaxed sailing holidays with shorter sailing distances, including more time for sightseeing and sometimes a nice land excursion.

Category D:
Sailing holiday specials, from ‘Sailing holidays with Yoga’ up to expedition sailing. Not every season available.

Category E:
Sailing holiday’s with extra sailtraining.

Category F:
Sailing holidays with also small children on board.