Explore Scotland under sail
Read why Wavysail Skipper, Jim Dobie thinks Scotland is one of the Best Sailing Adventures on Earth
With places on our "Sail Scotland" trips almost full, we catch up with Jim Dobie and find out why, despite sailing all over the world, he is constantly drawn back to the Scottish coast.
What is the uniqueness of sailing in Scotland?
There’s a kind of silence in Scotland that catches you off guard. The kind you don’t find on land anymore — where sea eagles ride thermals overhead, and you can anchor in a bay so still, it’s hard to believe you're not the only person left on the planet.
For professional skipper Jim Dobie, who’s sailed across every major ocean and guided hundreds through the highs and lows of offshore sailing, Scotland remains one of the most unforgettable places to take to the water.
“It’s probably one of the best places I’ve ever sailed,” says Jim. “And I don’t say that lightly.”
A Route with a Twist: The North Coast 500 by Yacht
Wavysail’s take on the classic North Coast 500 is anything but typical. Instead of road-tripping the famous loop, you sail aboard Big Blue, a purpose-built expedition yacht.
Starting in Oban, the trip unfolds over three legs:
Oban to Stornoway
Stornoway to Kirkwall
Kirkwall to Oban, via the dramatic Caledonian Canal
Each leg lasts around ten days, with time to explore historic harbour towns and sample a dram or two at local distilleries.
No experience is needed, but those with sailing knowledge will find plenty to get stuck into. “We always adapt to who’s on board,” Jim says. “If you want to learn, we’ll teach. If you want to soak it in and be part of something, that’s fine too.”
Wild Places, Quiet Moments
What sets Scotland apart isn’t just the dramatic scenery, though there’s no shortage of that. It’s the combination of remoteness, history, and the rhythm of the tides.
“You leave Oban and within an hour you’re spotting seals and sea eagles,” Jim says. “By the end of the day, you might be anchored in a loch with no one around, zero phone signal, nothing but you and the water. It’s like nowhere else.”
One of Jim’s favourite spots is Loch Tarbert on the island of Jura. You wind through a narrow, zig-zagging entrance, flanked by weirdly sculpted beaches. “Then suddenly you’re in this calm, perfect basin. No signal. Just peace.”
And then there’s the wildlife. Otters, dolphins, basking sharks — even the occasional whale. “You’d be amazed how much life is out there. And because it’s not busy, they’re not spooked. You see them properly, not just a flash of a tail.”
The Challenge Beneath the Beauty
Make no mistake — this isn’t a passive cruise. “Scotland keeps you on your toes,” Jim says. “You’ve got tides, tricky passages, changing weather. You need to be able to adapt.”
That means flexibility. The itinerary is a guideline, not a promise. “Sometimes the weather means we flip the route — go the other way, or stop somewhere else. But that’s the beauty of it. There are no bad options up there.”
This kind of sailing — responsive, instinctive, shaped by the elements — makes it special for Jim. “You're not fighting nature. You're working with it. That’s proper sailing.”
Who Is This For?
It’s not just for seasoned sailors or hardened adventurers. Jim says some of the most rewarding trips are with total newcomers. “People come on board a bit unsure — maybe never been on a yacht before. By the end, they’re crewing, navigating, and cooking at sea. They surprise themselves.”
What unites the crew isn’t skill, but mindset. “Curiosity. Openness. Willingness to disconnect and be part of something. That’s who this trip is for.”
A Different Kind of Travel
In a world that moves faster every day, sailing the west coast of Scotland offers a slower, deeper kind of experience. One where the tide shapes days, and the most unforgettable moments often come with no Wi-Fi and no plan.
“It’s not polished. It’s not packaged. But it is real,” Jim says. “And once you’ve done it, it stays with you".