Gliding along the deep blue waters of the west coast, anchoring in remote bays or visiting bustling island communities – for many, a sailing holiday on the Scottish west coast sounds like a dream. In this guide to sailing in Scotland, I’ll tell you how to turn that dream into reality. I’ll cover what it’s like to explore the coast by boat and share my top tips for an unforgettable sailing holiday in Scotland.

This blog post was commissioned by Stravaigin Sailing. All opinions are my own.

This post contains affiliate links from which I may make a commission. Find out more here. All opinions are my own.

Ever since spotting a sailing yacht anchored in the mirrorlike waters surrounding the Shiant Isles on a hot summer’s day, I’ve been dreaming of exploring Scotland by sailboat.

This dream finally came true when I was invited to join a west coast sailing trip with Stravaigin Sailing. We sailed from Oban around the Isles of Kerrera and Lismore and anchored overnight in a beautiful bay on the Isle of Mull.

It turns out that the west coast of Scotland is one of the best places in the world for sailing. With its rugged coastline, countless bays, sounds, sea lochs and islands, there are always new waters to explore.

In this post, I’ll tell you about my experience of sailing in Scotland aboard the Stravaigin and what to expect on a sailing holiday in Scotland. I’ll also include my top tips for booking your own sailing trip on the west coast, what to pack and how to get the most out of your time on board.

Why should you go sailing in Scotland?

There are many reasons to give sailing in Scotland a go – here are three to convince you.

1) Easy island hopping

Sailing in Scotland can take you to remote bays in the Inner Hebrides, the outer islands of the Western Isles and countless island communities. Instead of planning complicated ferry itineraries, you’ll enjoy island hopping with ease.

It’s easy to reach remote islands and anchorages to visit villages and towns that are otherwise hard to get to – especially if you don’t want to spend multiple days in one location.

Sailing in Scotland with Stravaigin Sailing

2) Memorable wildlife encounters

In the summertime, Scotland’s coastal waters are teeming with life. A sailing holiday on the west coast of Scotland is the perfect opportunity for wildlife watching in the water and in the air.

You may spot dolphin pods, orca from the North Isles or the rare West Coast Community, minke whales (especially around the Small Isles or basking sharks beneath the surface. In the air, keep your eyes out for majestic eagles, elegant gannets, goofy puffins and many more.

3) A flexible itinerary

Sailing is a great way to reach remote bays and uninhabited islands. It’s also an incredibly flexible way to travel since you’re not restricted to a road network – you can travel in any direction you chose.

When you travel on land (by car or public transport), water usually represents an obstacle. You have to take a ferry, find a bridge or follow a winding road around it. But when you’re on a sailboat, the coastal waters become your motorway of sorts. Unlimited adventure!

Sailing in Scotland with Stravaigin Sailing

Stravaigin Sailing offers fully-catered sailing holidays on the west coast of Scotland.

John Ormiston is the owner of the Stravaigin yacht and also the skipper. Fuelled by the adventure novels of his youth, he has had a lifelong passion for sailing and mountaineering. John has many decades of experience as a skipper. Not only has he always had a family boat for private use, but he has also worked as a professional skipper, often being hired by other people to take them out on their own boat.

With the Stravaigin, John fulfilled his dream to have a large boat of his own and the opportunity to take guests on immersive sailing holidays in Scotland.

The Stravaigin yacht

The Stravaigin is a 44 ft yacht that comfortably sleeps 8 people – that’s 6 guests and 2 crew. (Theoretically, there is space for 10 people but it would get a little crowded.)

That means that small groups are guaranteed on a sailing holiday aboard the Stravaigin. The yacht is also suitable and available for private charters.

There are four cabins in total. Two cabins with double berths are near the stern (rear of the boat); one cabin with double berths is in the bow and a fourth cabin with two bunk berths is also near the front.

Stravaigin has many charger outlets, so you can charge your phone and other devices as needed.

The boat has two toilets and a shower, as well as a galley kitchen and a bright, spacious saloon.

You can find a picture of the layout and all the technical specs about the yacht here.

Sailing Holidays in Scotland: Itinerary Options

Stravaigin Sailing offers trips departing from Oban and Mallaig, two major ports on the west coast of Scotland.

The sailing trips last between 3 and 10 days and there is a wide range of itineraries and destinations to choose from. Here are some highlights:

  • Around the Isle of Mull in 7 days, incl. detours to other islands like Iona, Staffa and the Treshnish Isles
  • Isle of Skye and the Small Isles (Canna, Eigg, Rum & Muck) in 7 days
  • A 10-day journey to the Outer Hebrides and the remote archipelago of St Kilda
  • Exploring the Southern Inner Hebrides from Islay to Jura, Colonsay and Gigha (7 days)

One thing to keep in mind is that while John will provide you with a suggested itinerary, weather and tidal conditions may require him to adjust the route, rearrange the order of destinations or substitute some sites for others.

The route may also be adjusted depending on your comfort level on board, for example, you might have the choice between a remote anchorage or anchoring in a port with access to restaurants, shower facilities etc.

Multi-activity Sailing Holidays

One of John’s specialities aboard Stravaigin Sailing is to offer multi-activity sailing adventures.

You may not be a passionate sailor (yet) or are still finding your sea-legs or someone else roped you into booking a sailing holiday in Scotland. Either way, you might be interested in adding another activity to the itinerary.

John works with local guides to deliver a variety of multi-activity trips throughout the year. This includes:

  • Sailing and Wild Swimming with a swim guide
  • Sailing, Hill Walking and Foraging with Heather Thomas-Smith
  • Whisky Cruises
  • Gaelic Culture Cruise with Dan the Merman (no language requirement)

The Stravaigin also carries a couple of paddleboards which guests can use while the yacht is anchored.

What route should you pick?

The best way to choose a route for your sailing holiday on the Scottish west coast is to contact Stravaigin Sailing and tell John about what you’d like to experience.

Depending on your timeframe, budget, sailing experience and interests, John will be able to recommend which of his scheduled sailing trips might be most suitable.

Note that most sailing holidays and adventures scheduled for 2023 are already fully booked. Contact Stravaigin Sailing directly to ask which trips still have space, or check their 2024 calendar to book ahead for the next season.

Tips for a Sailing Holiday in Scotland (& FAQ)

Do you need sailing experience?

No, you do not require sailing experience on any sailing holidays or adventures with Stravaigin Sailing. John advises that if it is your first time though, you book a shorter journey before going for a 7 to 10-day journey. The last thing you want is to spend a lot of money on a holiday you realise on day 2 is not your thing.

Can I learn how to sail on board?

Yes! John Ormiston is a qualified sailing instructor. While he no longer runs sailing courses, guests who are interested have the opportunity to learn about sailing informally on board.

No one has to help – John and his crew member can sail the boat on their own. But if you’re curious, or need something to do on board (more on strategies against sea sickness later), you can help with the sailing of the boat. This may entail hoisting the mainsail, controlling the steering wheel, or assisting in tacking the boat (i.e. making turns).

Should you join a group or privately charter the boat?

The answer to this question depends on your budget and who you are travelling with.

As a solo traveller, joining a scheduled group trip is the most affordable option. Private cabins are available but limited to one per trip.

If you’re travelling with your partner, family or group of friends, you may appreciate the opportunity to adjust the route and activities to your specific needs. However, consider that you’ll have to pay the cost of running the boat by yourself, so unless you share with 5 paying friends, it will be more expensive to charter the Stravaigin privately.

Note, that the Stravaigin is not available for “self-sail” holiday. Skipper John and his crew member are always on the steering wheel.

What does a typical day on board the Stravaigin look like?

The day starts around 8 am with fresh coffee, morning wildlife watching, an optional swim and a hearty, cooked breakfast in the saloon.

Depending on how far you’d like to go each day, if you’re keen to include other activities and of course the weather, you may spend the morning at your anchorage. You could go for a swim or take out the paddleboards, or John can drop you off on land for a wander before you sail on.

On other days, you may leave after breakfast and spend more time exploring your next destination.

Lunch is typically served at sea on your way to the next overnight destination.

John will find a place to anchor before dinner which – depending on weather conditions – you may enjoy up on deck or down in the saloon. There is always plenty of time to relax and enjoy some nibbles, and hopefully a dazzling west coast sunset.

The evening can be spent stargazing, trying drams from the bar or telling adventure stories around the table.

Time on board vs. on land

How much time you spend on land vs on board the yacht depends on your preferences / the preferences of the group. Some people prefer to sail all day, others would rather explore the islands. John aims for a good balance between both.

What if the weather is bad?

The Stravaigin is a big yacht and can handle any weather the Scottish west coast might throw at it. However, John wants his guests to have a good time, so will only sail if the conditions allow a comfortable experience.

The great thing about sailing is that if the forecast is bad in one place (or even worse – wind still), you can simply sail in another direction and escape the weather.

Food & drink on board

All trips on board the Stravaigin are fully catered. John and his first mate prepare all meals for you and source many of the ingredients locally. While you enjoy a walk across an island, John might be away to collect a bag of mussels from a local fisherman.

That said, vegetarian, vegan and gluten-free diets can also be accommodated.

The boat has a small bar with beer, wine and local whiskies and gins – although I don’t recommend drinking too much as sailing with a hangover is considerably less fun. Trust me ๐Ÿ˜…

What about seasickness?

Not everybody is born with natural sea-legs – meaning that some people take some time to get used to the constant movements of the yacht. If you know or are worried that you’ll react badly, here are some remedies and strategies to deal with seasickness:

  • Stay outside: The best way for me to overcome seasickness is to get fresh air. Stay up on deck (rather than below in the cabin or saloon), look at the horizon and take in the fresh air.
  • Eat ginger: Eating ginger can help settle an upset stomach. You can try ginger biscuits, candied ginger pieces or ginger tea – all things you can easily buy and bring with you.
  • Stay hydrated: This is probably just life advice. If you are actually sick on the boat, it’s super important to rehydrate.
  • Distract yourself: My favourite way to deal with seasickness is to distract myself. If I have something else to focus on, it’s much easier to forget about the weird feeling in my body. I spent most of my time at sea taking the steering wheel and learning sailing terminology from John.
  • Seasickness medication: If nothing else helps, there is a range of seasickness pills you could try. I recommend finding meds that don’t make you too drowsy. I’d also try them before your big sailing trip to see how you react to them.
  • Lie down: If all else fails, you may find comfort in retreating to your cabin and lying down. (I have in the past combined this with taking meds.)

You’ll be pleased to hear (maybe?) that there are sick-bags in the cabins throughout the Stravaigin yacht.

What to bring on a sailing holiday

Stravaigin Sailing provides a full kit list to help you pack for your sailing holiday in Scotland. Here are some of my top tips:

  • Plenty of layers: We had glorious sunshine during our sailing trip in April, but the temperature felt a lot lower because of the wind on the boat. Make sure you pack warm layers, a warm outer jacket, a waterproof jacket and trousers for wet days, a woolly hat and gloves. I actually brought my swimming dry robe instead of a puffer jacket.
  • Shoes and clothes that are easy to get in and out of, so it’s easier to get changed in close quarters. I really love my Barbour ankle rubber boots – they are the perfect travel shoe for Scotland and great on a sailing yacht.
  • A sunhat and sun lotion: While it felt chilly in the wind, the sun was beaming down on us. The sea reflects much of the sunlight back at you, so it’s extra important to protect yourself from the rays. Bring a hat to cover your head (nothing is worse than a burnt scalp, trust me) and sun lotion with high SPF. Top tip: Make sure your hat stays on your head even in strong winds.
  • Seasickness remedies – see above
  • Binoculars to spot wildlife along the coast, in the air and away in the distance.
  • If you’re into photography, bring a zoom lense(s) for the same purpose.

All bedding and towels are provided by Stravaigin Sailing, as well as personal flotation devices to wear up on deck.


Sailing on the west coast of Scotland aboard the Stravaigin was everything I dreamed of, and yet, it exceeded my expectations. Even though I haven’t quite found my sea-legs yet, I thoroughly enjoyed spending time on the boat and exploring the coast of Scotland in this unique way.

I can’t wait to plan another trip soon and hope you also feel inspired to give sailing in Scotland a go!

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3 thoughts on “Sailing in Scotland: Tips for a Sailing Holiday on the West Coast

  1. Julie says:

    Thank you so much for this blog post, it has inspired me beyond measure! ๐Ÿ˜€
    I booked with John just after listening to your podcast, and now reading this just makes me even more excited and impatient to get on the boat! ๐Ÿ˜‰

  2. Pingback: 'A Taste of Freedom' - Sailing on the Scottish West Coast

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