Get ready for Bucket List sailing and sights, with the opportunity for some real adventure sailing including a long passage!
A wonderful opportunity to get hands-on for 10 nights exploring some of Scotland’s most iconic islands by sail.
Under the expert guidance of your skipper you’ll experience the dramatic coastline, spectacular rock formations formed over 400 million years ago from your Beneteau 46 Oceanis.
Starting and ending in a couple of different ports, these adventures are the perfect combination of bucket list sailing and sights, and – weather permitting – you’ll have a chance at at a long passage to St Kilda or through the Pentland Firth. Imagine night sailing under the stars!
Routes for 2025
- Oban – Stornoway, 2 – 11 August
- Stornoway – Kirkwall, 14 – 23 August
- Kirkwall – Oban, 27 August – 05 September
- Oban Sailing Adventure, September 10 – 19
Some evenings the crew will drop anchor in a quiet secluded cove or pick up a mooring by sleepy harbour villages always taking the time to explore the sea loughs and gaze into the waters and watch for wildlife, otters, dolphins, seals, whales, and basking shark all resident in these waters. Or look skyward to see puffin, gannets and maybe a white-tailed sea eagle.
You will be guided by Jim Dobie, a hugely experienced Skipper and RYA Yachtmaster Examiner. Jim has a long history of successful race campaigns including being a Skipper in the 09-10 Clipper Round the World Yacht Race, 5 Sydney to Hobart races, 2 Fastnet races, Round Britain and Ireland Race
With only 6 guests per voyage everyone has their own berth (the boat sleeps up to 10) and you’ll get all-star personalised service with 1-2-1 calls before departure to ensure the voyage plan is well suited to all crew needs so everyone gets the most out of it.
Why you'll love this adventure
- Personalised and expert tuition from accomplished skipper
- Perfect mix of amazing natural wonders and epic sailing
- Small group size of max 6 guest sailors

Dates
Itinerary
Th trip starts (and ends) in Oban, Scotland. The itinerary will be planned around the best weather conditions yet the plan is to visit Tobomory, Skye or Col and St Kilda as well as Fingals cave.
For full details please make an enquiry!
What's included
- all food and drink (non-alcoholic) on board
- Safety equipment including a full safety briefing (of course)
- Your own cabin (unless otherwise stated)
Not included
- You’ll need travel insurance – this is a condition of joining – we’ll advise on the specific cover you need, but it’s essentially to ensure you’re covered if you fall ill on board
- Meals and activities ashore if we dock during the trip are not included, so you’ll want some “pocket money”
- Immigration and custom fees are not included if we travel to another country, you’ll need to ensure you’re eligible to enter that country, with the necessary documentation
Trip notes
Price
Min age
Accommodation
Meals
Who is this trip for?
Tour operator
There are few places as wild and unexplored as the open ocean. And if you’re going to explore it you’ll want to do so with an accomplished and experienced skipper alongside you at the helm. The skippers bringing these small group (max 6 guests) ocean voyages to life have at least half a million nautical miles under their belts so you’ll be learning from the best. Think small groups, amazing destinations and incredible ocean experiences. Whether you want the mileage for an RYA Ocean qualification, the thrill of taking a small boat to incredible destinations or the privilege of a sailing masterclass with hugely experienced skippers by your side, they’ll make it happen.

Enquire today
Scotland Isle Adventure Sailing
Please complete the enquiry form above with as much detail as you can and we will send you all the trip information and connect you with the operator so you can make a booking directly.
If you have queries and questions about the trip include those in your form and we’ll personally reply to you within 24 hours.
Why Book with Another World Adventures?
Book direct with the tour operator. No mark-ups, no fees.
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A most helpful, friendly and knowledgeable travel company!
Very helpful and provided lots of research material and excellent personal perspectives on the tall ship sailing trip I was interested in taking.— Martin
Excellent thoughtful service.
They were prompt and friendly, and so thorough and helpful in connecting me with my adventure.— Tina
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