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Explore the Outer Hebrides & St Kilda

  • Vessel: Flying Dutchman
  • Where: Oban, Scotland
  • Duration: 9 days
  • Embark: Oban - 20 July 2023, 18:00
  • Disembark: Oban - 28 July 2023, 10:00
Single berth in Twin Cabin Ensuite£1,245.00 £311.25
Twin Cabin Ensuite (single occupancy)£1,815.00 £453.75
Single berth in Twin Plus Ensuite Cabin£1,380.00 £345.00

Explore the Outer Hebrides and UNESCO site of St Kilda with traditional tall ship the Flying Dutchman.

Join tall ship the Flying Dutchman in the Scottish harbour town of Oban on the West Coast of Scotland. This adventure sailing holiday will see you follow in the footsteps of our Celtic ancestors to make the crossing to the ancient UNESCO heritage archipelago of St Kilda, exploring the Outer Hebrides along the way.

  • Fully crewed tall ship
  • Traditional sailing
  • Private cabins
  • Longer passages at sea
  • Half-board



The Outer Hebrides offers some of the most breath-taking and fascinating sailing grounds in the UK. One of our most popular sailing holiday destinations, the coasts and islands that make up the West Coast of Scotland offer so much variation for ours boats and guests, you will quickly see why our guests return year on year. Think remote anchorages where mountains run straight into the sea, miles of atmospheric landscapes, secret coves and uninhabited islands for walking trails ashore.

The main focus of this adventure sailing holiday is to reach the Outer Hebridean islands, the Shiants and as long as the weather is favourable, reach the far flung archipelago of St Kilda. The wind and weather will determine your route and destination so it is never 100% guarantee that St Kilda will be reached. The skipper and crew will have a better idea of what to expect from the weather as you board.


Hop aboard the Flying Dutchman at 6pm and after an introduction to the crew, dinner will be served at 7pm where you can get to know your fellow guests. (If you are arriving into Oban earlier, just let the boat know and you can drop your luggage off and spend some time exploring.) The route will be entirely dependant on the wind direction so there is no fixed itinerary but below is an idea of what we would hope to achieve.

An early start sees the sails set as we head for our first destination in the Small Isles to the island of Canna. Known as ‘the garden of the Hebrides’, Canna has fertile soils, green meadows and abundant wildlife. Recognised as a bird sanctuary since 1938, it supports over 20,000 breeding seabirds, including puffins, razorbills and guillemots. On our way we pass the impressive Duart Castle, which is a beautiful sight from the water.

Our sailing adventure to St.Kilda continues as we stop over on the outer Hebrides on the islands of Harris and Lewis. The Southern part of the islands has deep bays and high mountains with the West side of Harris home to stunning beaches flanked with dunes Machair (a unique flowering part). We will anchor here as we prepare for a good weather crossing to St Kilda.

The UNESCO world heritage site is a volcanic archipelago, with its spectacular landscapes, comprises the islands of Hirta, Dun, Soay and Boreray.  St.Kilda have some of the highest cliffs in Europe, which have large colonies of rare and endangered species of birds, especially puffins and gannets.

The archipelago has been uninhabited since 1930, but there are traces of more than 2000 years of human habitation. They contain the fragile remnants of a self-sufficient economy based on the products of birds, agriculture and sheep farming. On land, guests can walk through the abandoned village and take a more energetic climb to the edge of Britain’s steepest cliffs, past hundreds of small stone huts known as openings used to store the Guga. Rare Soay sheep roam here, a primitive breed of today’s domestic sheep.

Sail towards Stac Lee and Boreray to visit the largest gannet colony in the world. This majestic sight will enter you, millions of sea birds circling the cliffs and coming in to nest on the sheer cliff face.

Puffins, guillemots and auks all breed at this time of year. Get close to the caves and capture images! Seals are common, either sunning on rocks or fishing in the sound. Keen eyes can spot basking sharks and minke whales that come to feed in the plankton-rich waters of the western islands. Not to mention the eagles and deer that roam the sky and land.

Set the sails back across open waters as we head for the island Barra, where we moor in Castlebay. Visit the surviving medieval Kisimul Castle before we head back towards the island of Mull for our final night in the fishing village of Tobermory.

Life onboard

One of traditional sailing, sea-faring tales and breath-taking destinations, sailing with the Flying Dutchman is a far cry from its ancestral name. Although a traditionally rigged vessel with an authentic wooden boat feel throughout, the Flying Dutchman has been fitted as a charter vessel to a high, modern standard – providing guests with an authentic sailing experience while ensuring comfort and mod-cons are not forgotten. With private twin en-suite cabins, large communal spaces both above and below decks and an onboard chef for hearty home-cooked meals after a day of good sailing – sailing with the Flying Dutchman is an experience you won’t forget!

Enjoy a balance of traditional sailing harnessing the power of the wind to spending time exploring ashore in hard to reach locations away from the tourist hustle and bustle. The half board nature of the Flying Dutchman means that guests are able to enjoy the cuisine and fresh produce of the local area.

Read more about what to expect from life on board the Flying Dutchman.

Flying Dutchman

Guest berths: 24 Rig: Schooner

Built in 1903, the Flying Dutchman has been recently re-fitted to a high standard for comfortable sailing holidays in Scotland. There is a huge 480m² sail area to propel you through the water and on the Flying Dutchman you will have the option to participate in helping the different sails up and getting to know all the different crafts. You will be guided by an experienced crew to help you with all the different crafts on the ship. If you want to steer the ship, do not hesitate to ask the captain.

The main saloon is a generous space with plenty of portholes providing comfortable area with lots of natural light. A combination of sofas and tables make it a great communal area to get to know your fellow guests and enjoy meals inside. There is also a well-stocked bar within the saloon area too. Below decks, there are ten ensuite cabins for guests with bunk beds, all with heating and air-conditioning depending on where you are in the world.

The rear deck is layered with wood, which emphasises the traditional atmosphere of the ship. On the main deck there are 3 different tables and couches to sit on, this area is covered to protect the guests from the rain. This offers the opportunity to stay outside and eat your dinner under the stars.

Deck plan

Flying Dutchman deck plan More about Flying Dutchman


  • Are all meals included?

    Yes - all meals are included in the price (Breakfast, Lunch, Dinner, Hot Drinks) Please note that alcohol/soft drinks are not included. There is an honesty bar onboard.

  • Are there any added extra's?

    No, unless you go ashore. Excursions are not included.

  • Can you cater for dietary needs?

    Vegetarians only.

  • What language is spoken onboard?


  • What are the sleeping arrangements?

    10x double ensuite cabins and 1x four berth ensuite cabin

  • How many toilet/showers does she have?


  • Is there WIFI?

    No, but you should easily be able to reach 3G/4G from the shore.

  • Can I charge my phone/Camera?


  • Are there life jackets provided?


  • Are Waterproofs provided?


  • Do I need sailing experience?

    No, absolutely not! Just a lust for adventure.

  • 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 bedding included?

    All bedding and wash towels are included. Please bring a swimming towel if you wish to swim ashore.


From: Oban

To: Oban

Buckie is very close to Airport Inverness. There will a free minibus from Inverness airport to take people to the boat in Buckie.

To get from Oban, the bus is the best means of transport, whether you’re flying from Edinburgh or Glasgow (15 minutes difference). From both airports there is a transfer bus every 30 minutes to Buchanan (Glasgow) Bus Station, from where the bus to Oban departs.
For more information: Citylink.co.uk
If you wish to travel by train, first take the bus to Glasgow. Then you can take the train from Glasgow: Scotrail.com

Klm flies to Edinburgh and Glasgow.
EasyJet flies to Edinburgh, Glasgow and Newcastle.
Flybe flies to Edinburgh, Glasgow, Aberdeen and Inverness.
Ryanair flies alone to Edinburgh.

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