United Kingdom · September 10 - 19 2025
Scottish Isles Oban Sailing Adventure
The perfect combination of Bucket List sailing and sights, with the opportunity for some real adventure sailing including a long passage
BOOK NOWOverview
Sail Scotland in 2025! Join us on our Scottish Isles Sailing Adventure, departing Oban for 10 days and explore some of Scotland’s most iconic islands by yacht with Jim Dobie. We think this is the perfect combination of bucket List sailing and sightseeing. Real, hands-on sailing including the potential for a long passage and possibility to visit the UNESCO heritage site at St Kilda and through the Pentland Firth. We can even add some night sailing if the group wishes and weather allows as well as evenings, at anchor, allowing us to enjoy time ashore in the sleepy harbour villages along the coast. Jim Dobie is a hugely experienced Skipper and RYA Yachtmaster Examiner meaning you can use the trip to brush up on sailing skills, with plenty of time for one to one mentoring, or simply enjoy being part of the voyage. With a maximum of six crew aboard our comfortable yacht, you will have space to relax and plenty of opportunity to adapt the itinerary to the groups wishes.
Highlights
Skippers
Itinerary
Previous
Next
What's Included
What's Included
All food and drink (non-alcoholic) on board
Safety equipment including life-jackets.
All mooring and port entry fees for the boat.
• Hands on sailing, watch keeping, helming and opportunity to fully immerse in life on board.
Overnight accommodation onboard, your own bunk and bedding
• Waterproof Clothing available to hire
What's Not Included
• Travel to and from Oban
• Meals Ashore
• Entrance fees to visitor centres or distilleries
• Sailing & Travel Insurance
You'll Be Staying Here
Big Blue
Big Blue is a Beneteau Oceanis 523. Spacious, comfortable and well equipped she is a powerful but easily handled yacht.
In Big Blue we cover the ground quickly which leaves more time for exploring ashore or sailing further. `Big Blue` is very well equipped for offshore sailing and carries a paddle board and inflatable kayak for exploring the anchorages you will visit.
We have 4 sleeping cabins, one is for the Skipper and the others consist of 1 large double and 2 smaller double cabins. All three can be converted into twin cabins - the bunks can be divided by lee cloths if preferred.
All cabins are en-suite. Bedding is provided. On board comfort is a priority - the layout offers privacy and there are heating outlets in all cabins.
FAQs
Do I need to be experienced in sailing?
We design the trips for a wide range of experience which that means that even if you’ve not sailed, our experienced Skippers will ensure you have a fantastic time
The longer legs will suit “mile builders” who already have some sailing qualifications, and we can spend time supporting you with everything from helming to sail trimming or passage planning as you wish!
Before you join, we’ll ask you about your previous sailing experience and what you want to get out of the trip. That way, we’ll tailor the tour to your specific needs
What's the cancellation policy?
The group size is kept very small on our trips which gives you a real ‘masterclass’ with our highly experienced Skippers However, that means each place is valuable and we need full groups
We ask for a 10% deposit to secure your berth, with the balance being due 6 weeks before departure
If you cancel your place over 6 weeks out, we’ll retain the deposit, but no other fees will be due
If you cancel 6 weeks or less, the full price will be payable
What should I bring?
We’ll share with you a kit-list which will be adapted to the trip you’re taking
A good sleeping bag and some decent deck shoes (or sailing boots) are the main things to organise, otherwise it’s layers of clothing adapted to the conditions you’re likely to encounter
Bring a camera – if you want to bring a drone, let us know beforehand and bear in mind drones tend not to be waterproof and are carried / used at your own risk!
How adventurous is it?
We want everyone to get the most out of their time on board – so we’ll work around your wants
However, our trips are designed for you to take an active role – that means, for example, we’ll take turns in cooking (all the menus are planned already and step by step instructions given, so you don’t need to be a masterchef!)
You can get tips and instruction on all aspects of sailing from our Skippers and get as involved as you want, grinding, trimming, helming and learning – on the other hand, there’s also plenty of time to relax and just take in the beautiful Ocean scenery. It’s your trip!
We aim to do some night sailing (sailing under the stars is amazing!) so we will run a watch system.