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Tall Ship Sailing Skye & the Small Isles

  • Vessel: Flying Dutchman
  • Where: Oban, Scotland
  • Duration: 8 days
  • Embark: Oban - 30 April 2023, 18:00
  • Disembark: Oban - 7 May 2023, 10:00
Single berth in Twin Cabin Ensuite£1,010.00 £252.50
Twin Cabin Ensuite (single occupancy)£1,490.00 £372.50
Single berth in Twin Plus Ensuite Cabin£1,105.00 £276.25

Sail and explore Skye and the Small Isles 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 in the inner Hebrides will focus on sailing and exploring the Skye and the Small Isles with breath-taking landscapes, historical castles, abbey ruins and of course, a plethora of wildlife waiting to be discovered.

  • Fully crewed tall ship
  • Traditional sailing
  • Private cabins
  • Island hopping
  • Half-board


The Small Isles, Scotland

Made up of four islands; Rum, Eigg, Muck and Canna, the Small Isles have much to offer. Breathtaking coastal landscapes, untouched nature, secluded sandy beaches and idyllic retreats, make for the perfect sailing holiday destination.

The island of Rum is a paradise for wildlife and is home to the impressive but now derelict Kinloch Castle. The island of Eigg attracts archaeologists and ornithologists with its fascinating geology and biodiversity. The island of Muck is the smallest of the islands and is easily explored on foot or by bicycle. Canna is finally the westernmost of the Small Isles and is run by the National Trust for Scotland as a farm, but also offers a cafe-restaurant, an excellent meeting place for guests and inhabitants of the island.


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.

The island of Muck is our first destination as long as the weather and wind permits. Only 3 km long and 1.5 km wide, it is the smallest of the “Small Isles” with 38 permanent residents. With a fertile hillside landscape and white sandy beaches there are plenty of places to explore. Take a hike to the highest point of Beinn Airein for some impressive highland views or visit the prehistoric fortress of Caisteal an Duin Bhain.

Our next stop is the island of Rum. The island offers extensive hiking trails into the mountains with rum ponies, sea eagles and deer to name but a few island residents. Rum inspires scientists worldwide with its unique geology, including the core of an ancient volcano that formed the now visible Rum mountains. One of the most popular day trips is a tour of Kinloch Castle, giving visitors a fascinating insight into the life of the Bullough family who built the castle between 1897 and 1900. The castle houses a “orchestrion” made in Germany, which imitates the sound of a whole orchestra by scanning punched paper rolls.

The Isle of Skye is a truly magical place. The largest island of the Inner Hebrides, Skye is home to some of Scotland’s most famous landscapes. This island will inspire you in many ways, with its stunning mountain chains and miles of coastline to discover. Visit the Talisker brewery, take a hike or discover the island by bus!

Set sails for the picturesque harbour village of Tobermory on the island of Mull. Explore ashore, take a visit to the whiskey distillery, visit the small Tobermory Museum and the discover the Marine Exhibition. Enjoy the untouched, wild nature of the Scottish islands, the rugged beauty of Mull, the silence on the water, the indescribable landscape, the jagged coast with its surprising bays and the quiet fishing villages.

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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