The Orkneys to Fair Isle and The Shetlands

Vessel: The Orkneys to Fair Isle and The Shetlands
Where: The Orkneys

Sorry we’re full!
This voyage is fully crewed. Check out our voyage finder to see what else we have available.

Depart from the beautiful village of Kirkwall, exploring the beautiful archipelago of the Orkney and Shetland Isles under sail in Cherokee.

The itinerary is, of course, dependent on the wind and tides but our crew know all the hotspots off the beaten track. Cherokee will look to cross over to Fair Isle, a distance of about 38 miles. The trip will show you the beauty of these islands from the water, and you will also have the chance to explore on foot. Relax in sheltered anchorages and watch picturesque sunsets, and if we are blessed with dark skies, the stargazing from the deck is breathtaking.

Fair Isle is definitely a highlight, so Jouke will anchor Cherokee for a day to give his guests the opportunity to walk along the spectacular north coast. The atmosphere on the Island is unique, with nothing in the harbour except stunning flora and fauna and a Bird Observatory. There is more than meets the eye to this Observatory though – it is also a relaxed bar, offering a beautiful view of the harbour (with many seals) and where those interested can learn more about all the rare birds found on the island (such as the puffin or Skua). In the evening guests will be able to walk from the harbour up the cliff where you can see hundreds of Puffins go ashore on their way to their nest. Due to the lack of tourists, the birds aren’t wary of humans and you can approach them up to one metre – a truly unforgettable experience.

The wildlife only continues to impress throughout these islands, from high moorland to immense sea cliffs, unspoilt wetlands and pastures, they are a haven for sea life, birdlife and mammals ashore. Orkney has 36 Sites of Special Scientific Interest and 13 Special Protection Areas and 13 RSPB nature reserves. Towering cliffs are home to over a million seabirds, including puffins, thousands of grey and common seals and an array of marine mammals. There are frequent encounters with Common, Bottlenose & Whitebeak dolphins on board these trips, and Risso & Whitesided dolphins are also occasionally sighted. Basking sharks have been scarce the last few years but are still seen and seem to be returning – and we know the hot spots! There are plenty of whales in this part of the world too. Our most common encounters are with Minke – Humpbacks are a less frequent visitor, while the real star of the show is the resident pod of Orca if you’re lucky enough to see them gliding through the water. So keep your eyes peeled and have your binoculars at the ready!

Onwards from Fair Isle, Cherokee will cross over to the Shetland Islands, and depending on the weather this will probably be Grutness Voe. Here, guests will be able to walk up to the cliffs, with stunning views over the Atlantic Ocean and Sumburgh Head. Alternatively, there is a beautiful walk to Jarlshof with prehistoric and Viking excavations that entice many. This sailing holiday will finish in the lovely harbour of Stromness, where guests will enjoy a delicious dinner in a local restaurant (not included in the price). Jouke the Skipper has sailed these waters for a few years now so has a good knowledge of the hotspots off the beaten track. His crew are able to sail the boat without guest input but they are more than happy and willing for guests to get involved! The onboard chef will bring you breakfast, lunch and tea included in your ticket price so climb aboard for great food, exhilarating sailing and wonderful wildlife.