United Kingdom · August 27 - September 5 2025
Sail Kirkwall to Oban via Caledonian Canal
Leg 3 of our Sail the Northcoast 500 tour
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Overview
Join our unique twist on Scotland's famous "Northcoast 500" as we sail it on Big Blue, our beautiful expedition yacht. You can join one or all three of the legs, combine it with driving or simply join this lovely tour of Scotland under sail. Leg 3 will take us from Kirkwall, in the Orkney isles back to Oban, routing West via Wick and Inverness before entering the famous Caledonian Canal. This is a real "bucket list" for many sailors which completes our grand tour of Scotland!
Highlights
Comfortable Yacht
a large , comfortable and practical cockpit she has an uncluttered layout with high quality teak finishes in the cockpit. The twin wheels allow a choice of comfortable helming positions and easy viewing when berthing. She’s comfortable and beautifully kitted out with 8 berths, so there’ll be plenty of space on board. She’s perfect for long trips. You’ll have your own berth.
Highly experienced Skipper
Jim Dobie will be your Skipper for the duration of the trip. A hugely experienced Skipper and RYA Yachtmaster Examiner who has sailed almost every ocean of the world. Jim is a well-respected training skipper and examiner, known for his patience and ability to share his passion for ocean sailing with those around him.
Scenic, Adventurous Sailing
A fabulous trip to the very North of Scotland, weaving through the Orkney islands - exact itinerary will depend on the experience of the crew, their wishes and the weather!
Skippers
Jim Dobie
A hugely experienced Skipper and RYA Yachtmaster Examiner who has sailed almost every ocean of the world, leading expeditions to some of the remotest places including the Galapagos, Cook Islands, French Polynesia and Tasmania. Jim is experienced, not only on, but also under water, as a Scuba Diving Instructor delivering expeditions to the Great Barrier Reef, Oceania and Asia.Jim has a long history of successful race campaigns including skipper for the 09-10 Clipper Round the World Yacht Race, competed in five Sydney to Hobart races, two Fastnet races, Round Britain and Ireland Race and many other offshore race events
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
Accommodation
Leg 3 only
Single Berth
Your own comfortable berth with plenty of storage space (shown is a double cabin, which will be split with a Lee cloth)
FROM$4,048.94 /pp
Double cabin (two people sharing)
A spacious double cabin
FROM$2,700.42 /pp
Full Northcoast 500 - all three legs
Gallery
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.
Related Blog Posts
Read about our previous Scottish adventures
Heather Deary · Sat 16 Sep 2023
Wavysail Scottish Islands Adventure 2023
Heather joined Wavysail's first Scottish adventure this summer - read about her experience of sailing the coast of Scotland under the expert guidance of Jim Dobie.
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 8 weeks out, the deposit is fully refundable, between 6-8 weeks, we will retain the deposit.
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
All bed linen is provided as well as safety equipment. You will need some decent deck shoes (or sailing boots), 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!