Sailing to the Orkney Islands

Your Sailing Area

Kirkwall – Peterhead, Scotland

Join Cherokee in the harbour of Peterhead on the East coast of Scotland.

A sailing holiday along the Scottish East Coast offers the chance to visit authentic fishing villages and working harbours such as Peterhead, Wick, and the atmospheric small harbour of Whitehills. Cherokee will cover daily sailing distances between 25 and 47 miles depending on the weather and tide. The sailing area, the Moray Firth, is rich in marine life, with frequent sightings of seals, dolphins, orcas, and even whales. Crossing over to the Orkney Islands from the mainland involves sailing over the Pentland Firth, known for its strong tidal streams, which can reach 16 knots during spring tide.

Upon reaching the Orkney Islands, we will sail into the shelter of Scapa Flow, where we will spend the night on a small island. Here, we can take a short walk and enjoy beautiful views of the island of Hoy and Scapa Flow. The following day, an option is to take a long walk to the famous ‘Old Man of Hoy’, offering spectacular views over the ocean and the cliffs. After visiting the atmospheric port of Stromness, we will sail to the island of Rousay, enjoying the beautiful sailing trip and rustic surroundings. The next day, there will be an opportunity to take a nice walk to an estate with a beautiful garden and rare trees, or alternatively, visit some impressive Bronze Age excavations. The trip will conclude with a short sail to Kirkwall, marking the end of this sailing holiday.

Kirkwall is the largest town and capital of the Orkney Islands, Scotland. It is known for its rich history, including its well-preserved Norse architecture and ancient sites such as the 12th-century St. Magnus Cathedral. The town’s picturesque harbour, charming streets, and friendly atmosphere make it a delightful destination for visitors.

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The wildlife in the Orkneys is spectacular;

… from high moorland to immense sea cliffs, unspoilt wetlands and pastures, it is a haven for sea life, birdlife and mammals ashore. Orkney has 36 Sites of Special Scientific Interest 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 show’s real star 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!

All voyages for Cherokee

Cherokee

Guest berths: 8 Rig: Cutter

In 2008, Jouke Lemmer purchased Cherokee after spending years sailing with his father’s ship amongst others. Cherokee was built in 2000 by award-winning boat builders J & J Design and a year after buying her, Jouke refitted Cherokee radically, transforming her into a truly comfortable charter vessel, giving her a cutter rig and space for a generator so as to offer his passengers power and hot showers!

She is a fast, 16m vessel with a stunning teak deck and spacious cockpit, and she operates with two crew members (her skipper and the bosun/chef). Cherokee is exceptionally good at what she was built to do – pure sailing. Read more about what to expect with life onboard here.

Jouke sails his ship all over the northern hemisphere, leaving Cherokee’s home port of Rotterdam in May and sailing anywhere from the Hebrides and the Channel Islands, the Faroe Islands and Ireland or even down to the North coast of Spain before making the journey back to Holland in October. Join him and his wonderful ship for the adventure of a lifetime – think exhilarating sailing, bucket list destinations and top-notch hospitality.

Deck plan

Life on board Cherokee

A custom-fit charter vessel, Cherokee, has been designed to ensure her guests enjoy comfortable offshore sailing adventures.

GETTING INVOLVED

Sailing with Cherokee certainly ticks the adventure travel boxes with a continuous A to B sailing schedule throughout the season. Skipper Jouke (pronounced Yow-ka) believes this is the best way to experience as many destinations off the beaten track as possible and loves to share his sense of adventure with guests.

Guests are actively encouraged to get involved with all aspects of sailing under Jouke’s relaxed guidance. Take the helm, help with the winching of the sails, anchoring and basic chart navigation. Skipper Jouke was born at sea, the son of a Baltic Sea Captain and a naval architect. You could not be in safer hands when he’s back on land!

SLEEPING & RELAXATION

With four private guest cabins, comfortable bunks, and two bathrooms at either end of the boat, Cherokee can easily accommodate solo travellers, adventurous couples, or groups of friends or family. Clever storage offers plenty of locker space for guests in each cabin. The boiler runs off the cooling water of the generator, so there is plenty of hot water for washing and showering!

Below decks, she offers a comfy & spacious saloon perfect for eating, playing cards or reading a book. You’ll find beautiful panelled mahogany interiors, giving the ship that classic feel. A well-equipped galley opposite the saloon provides a perfect social space, ready to bring you delicious food after an exhilarating day of sailing. Eat under the stars if the weather allows in the spacious cockpit, offering comfortable couches and a good-sized table. If the weather takes a turn, the crew will put up the cockpit tent, offering you shelter and warmth in the fresh air.

AUTHENTIC OFFSHORE SAILING

The boat is owned and sailed by experienced skipper Jouke, and there is a ‘bosun’ who also cooks. The bosun will prepare dinner as you arrive and after breakfast on your first morning aboard Cherokee, you can be guaranteed a relaxed start to your sailing holiday.

Jouke and his crew try to use the engine as little as possible, sailing into port as much as possible. Cherokee only clocks up about 180 motoring hours yearly, which is pretty impressive. Due to this, as with most of our vessels, the days of your holiday are subject to the weather, using the tide as your clock. Guests aren’t presented with a tight schedule or itinerary for this reason, making the trip much more adventurous and flexible.

Kit list

Cherokee has limited space for possessions, 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 a travelling light principal with lots of lightweight, easy-drying layers. Below is a list of recommended items, these are not mandatory and those that have sailed before may have their own preferences!

• Walking boots/shoes for onshore & light shoes/trainers (with good grip)
• Wash towel – micro fibre is lightweight and quick drying!
• Swimsuit and swim towel
• Lightweight, quick-dry clothes (base layers, fleece and synthetic tops are lightweight and quick-drying!)

It can be quite a few degrees colder out at sea, so please bring many layers even if the forecast seems like a warm week!

• Warm, windproof and waterproof coat  and trousers 
• Waterproof boots
• Sun cream (please use reef-safe, eco products where possible)
• Sunglasses and a warm hat/cap
• Small personal first aid kit and any medication you may need
• Camera/binoculars 
• Refillable water bottle
• Personal wash kit (please use reef-safe, eco products where possible)
• Smidge repellent 
• Charging cables for personal devices 
• EU 2pin adaptor
• A good book to read!
• We advise sleep masks and/or earplugs!
• Consider a small backpack/bag for onshore exploring.

What’s included

• Full board (breakfast, lunch, dinner, snacks, hot drinks)
• All bedding (pillow, sheets & duvet) and wash towel
• Full crew plus tuition
• Fuel fees
• All tender trips to and fro the boat
• Lifejacket
• Use of onboard stand-up paddle-boards

What’s not included

• £85 board cash per person
• Swim towel or wetsuits
• Alcohol
• Any flights
• Transit hotels
• Travel to and from the boat on the day of joining/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 the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.

Please read more information on our Insurance guidelines page.

This voyage might be more than 12 miles offshore.

FAQ

• Are all meals included?

  Yes, all meals on board are included in the price. (Breakfast, lunch, dinner and hot drinks)

• Can you cater for dietary needs?

  Yes, please let us know when making your booking.

• Are there any added extras?

  There's an honesty bar for soft drinks and alcohol.

• What are the sleeping arrangements?

  Cherokee has two twin berth cabins and two double berth cabins for guests.

• Is there a porthole in my cabin?

  Yes, all cabins have either a hatch or porthole.

• How many toilet/showers does she have?

  Cherokee has two toilet/shower rooms.

• Are bedding and towels provided?

  All bedding and a towel is included but please bring your own swim towels (if needed). Micro-fibres are a great lightweight, quick-drying alternative.

• Is there a hairdryer on board?

  No, please do not bring one. The sea breeze makes a great natural alternative!

• Will I be able to wash my clothes?

  No, Cherokee does not have laundry on board.

• Is there heating onboard?

  Yes, there is heating on board.

• Do I need to tip the crew?

  Tips are not mandatory but are welcomed by the crew!

• What language is spoken on board?

  English and Dutch.

• Is there WIFI?

  No! It's time to disconnect from the modern tech and reconnect with nature! When within shore range, you should be able to reach 4/5G. Please make sure you have international roaming set up on your data plan.

• Can I charge my phone/Camera?

  Yes charging facilities are available when the generator is running.

• What is the currency on board?

  Whatever the local currency is in the sailing destination.

• Do I need sailing experience?

  Not at all.

• How do I get on and off the boat?

  Cherokee is often at anchor so you'll need to be comfortable climbing in and out of the tender dinghy. She has a dropped transom with steps so getting on/off the boat is fairly easy.

• Are there life jackets provided?

  Yes.

• Are Waterproofs provided?

  You can hire Sailing suits for £35 for the week.

• Does the boat have any water toys?

  No.

• Will I be sea sick?

  Everyone reacts differently but we recommend if you are at all worried to take some medication 24 hours before departure.

• Is there an age limit?

  Over 12's on most voyages.

Travel Planning

From: Peterhead

To: Kirkwall, The Orkneys

To see where the ports are, along with your likely sailing area, please view the sail area & highlights.

Getting There

Peterhead, Scotland

Peterhead has a train station so you can either fly to Edinburgh and catch the connecting train with Scotsrail or take the whole route by train.