Our sailing holidays in Scotland

Visit Scotland under sail and you could find yourself gliding alongside big wildlife. You might be in the remote, far north of the British Isles, but you won't be alone: there are seals, whales and dolphins in abundance. When you book our sailing holidays in Scotland, you'll discover the islands aren't as isolated as you'd think. Cross to Ireland, or continue round the coast following the North Coast 500 by sea, on a bonny boating adventure. Our sailing holidays in Scotland ensure that you’re not just a wake in the water, but are contributing positively to nature and communities on the islands – whether you’re eating sustainably caught seafood in a family-run local restaurant, or using a sailing company who donate profits to conservation charities and wildlife research.

Oban to Stornoway sailing holiday, Scotland

From £2495
10 days ex flights
Join the Adventure as we sail the Western Isles of Scotland
Small group2026: 20 Jun

Sail the North Coast 500, Scotland

From £6495
27 days ex flights
Adventure sailing around the north coast of Scotland
Small group2026: 20 Jun

Wick to Oban sailing holiday, Scotland

From £2495
10 days ex flights
Join leg 3 of our full NC500 sailing tour
Small group2026: 14 Jul

Stornoway to Wick sailing holiday, Scotland

From £2495
10 days ex flights
Join leg 2 of our full NC500 sailing tour
Small group2026: 2 Jul

Skye and the Small Isles sailing holiday

From £1600 to £2960
9 days ex flights
Sail Scotland's Small Isles and visit spectacular Skye
Small group2026: 5 May, 10 May, 30 Jul, 18 Aug, 26 Aug, 29 Aug, 9 Sep, 13 Sep, 16 Sep, 2027: 29 Apr, 10 May, 15 May, 14 Jun, 30 Jul, 14 Aug, 18 Aug, 26 Aug, 8 Sep, 9 Sep, 13 Sep

Wildlife sailing holiday in Scotland

From £1000 to £2960
6 days ex flights
Extraordinary wildlife above and below the waves
Small group2026: 14 Apr, 5 May, 7 Jun, 24 Jun, 13 Jul, 14 Aug, 8 Sep, 1 Oct, 2027: 13 Apr, 22 Apr, 9 May, 29 May, 14 Jun, 17 Jul, 21 Aug, 9 Sep, 1 Oct
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
Responsible Travel, Travel Team

Sailing holidays in Scotland highlights

What does sailing in Scotland entail?

Our sailing holidays in Scotland are on boats with professional crews. On some holidays you participate in the sailing of the boat, and become part of the crew. On others, you’re playing the role of relaxed passenger and chief wildlife spotter. In the day, if weather permits, you’ll be going underway using the power of the wind – and the tides, which are strong in Scotland – but you’ll have a motor to act as back up, too. When the sun sets, you’ll be anchored up somewhere peaceful – generally our holidays don’t go underway at night.

Sailing boats are built to cut through the water on narrow hulls, and it means that they are often not very roomy below deck, especially racing and expedition yachts; you will need to pack light. You won’t want to spend time in your cabin unless you’re sleeping. To navigate the odd rain shower, expect to wear waterproofs or oilskins on deck, or retreat to the mess to cosy up around the table and play cards. If you want a bit more space, some of our boats are available for private charter.

Wildlife watching on a sailing holiday

A sanctuary for wildlife that can’t be found in other parts of the UK, Scotland is home to internationally significant numbers of seabirds, spread over hundreds of islands, and there are over 8,000 wildlife species in its seas and inland waters. For sailors, this means great chances to interact with animals around the boat. If you’re lucky, this might be a pod of dolphins passing under your hull, seals on the rocks, or an osprey spotted on the hunt.

On our responsible sailing holidays you’ll be sailing with passionate crews who follow wildlife watching advice to the letter, and are especially mindful around breeding bird colonies – sailing boats often have better views of these on cliffs than observers on land. Bring your binoculars.

Food and drink on a Scottish sailing holiday

There’s no better simple pleasure than putting out a fishing line when you’re underway, getting a bite and calling your crew to slow down the boat so you can reel in your catch. Alongside some of the freshest seafood you can eat, our sailing holidays in Scotland are about whisky tasting on islands where the peatland imparts a smoky taste to every bottle, and trying sustainably sourced venison, and freshly-grown fruits and vegetables – is there anything better than a Scottish raspberry?

Where to go on a Scottish sailing holiday

The Inner Hebrides are a popular sailing ground, as going by boat is a great way to see popular Scottish holiday destinations, whilst skipping the crowds. That means finding quiet anchorages off the beautiful island of Skye, Islay, Jura, Mull, Staffa and the Small Isles.

The Western Isles, also called the Outer Hebrides, includes Barra, North and South Uists, Benbecula, Harris and Lewis. Close together, but more remote than the Inner Hebrides, they form a long chain that boats can explore in short hops.

Far north enough to enjoy a lot of daylight hours in summer, Orkney feels wild and remote – and with just 18 of its 70 islands uninhabited, it’s easy to find quiet corners where you can birdwatch, feel the wind in your hair, and pretend you’ve just arrived, Viking-style, across the North Sea from Norway.

Our Sailing holidays in Scotland reviews

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Sheila Jelfs16 May 2025
We enjoyed marvellous weather and enjoyed every moment, whether sailing, at anchor, or exploring our beautiful destinations. The wildlife we saw was really thrilling. Possibly the best holiday we have ever had, even as experienced travellers.read more
Alan Ross05 May 2025
It was a fantastic experience. Being looked after by a very experienced skipper, Stewart, and having excellent food freshly prepared by our cook/mate. The encounter with a pod of dolphins when we were approaching Bunnesan was out of this world. They stayed with us for about 20 minutes and the experience was absolutely fantastic.read more
Michael Carvey28 Apr 2025
Very good. Staff worked hard to make it a great holiday.read more
Audrey Aimer-Emslie17 Sep 2025
It was enjoyable even if our plans had to be changed. Glad that our safety and wellbeing was always a high priority. Staff always helpful and considerate.read more
Written by Eloise Barker
Photo credits: [Page banner: Andrew Wood] [Oban: Gunnar Ridderstrom] [Highlights: Draco2008]