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    Self Guided Walking Holidays – Your Questions Answered

    15 min read

    By David Russell
    More by David

    Ready to take on one of Scotland’s most iconic long-distance walks? Need a little help along the way?

    These walking holidays allow you to take on a long-distance walking trail at your own pace but with all the benefits of our support. We will arrange all accommodations, daily luggage transfers, route notes, maps, helpful tips and will be available for 24 hour on-call support.


    We offer self-guided itineraries for 4 of Scotland’s most famous long-distance hiking trails:

    • The West Highland Way – One of the world’s classic treks. This 100 mile walk starts just north of Glasgow and journeys up to Fort William in the heart of the Scottish Highlands.
    • The Rob Roy Way – Following the footsteps of one of Scotland’s most infamous outlaws. Hike through rolling moorlands and ancient woodlands on this historic journey.
    • The Speyside Way – Hike from the coast and head inland to the foothills of some of Scotland’s highest peaks. This 65 mile hike travels from the eastern Moray coast into the Cairngorms National Park.
    • The Great Glen Way – Traverse Scotland from coast to coast. Soak up the views along Loch Ness and keep an eye out for Nessie on this 73 mile hiking adventure.

    These routes and more are also available as Guided Walking itineraries and can be customised further as part of a Tailor-Made holiday.

    We offer a range of Self-Guided walking holidays. If you’re a little unsure what to expect, read on to find the most common questions answered.

    When can I do the hike? Are there set dates? Read More

    Our routes can be hiked between April and October. You can choose any date you like to start the hike and we will make all the arrangements to suit provided there is available accommodation. We recommend you try to avoid a weekend start date as this means accommodation is usually easier to find.

    self guided walking holidays

    Above Loch Oich on the Caledonian Canal and Great Glen Way walking route.


    I want to hike on these dates. Is it available? Read More

    Because there are so many possible accommodations we can not hold up to date availability for every one. We will be happy to advise the likelihood of being able to hike for the dates you give, but we need to take a deposit payment so we can make the bookings to confirm your dates.

    What’s the weather like? When is best for hiking in Scotland? Read More

    Scotland has famously changeable weather, so whenever you hike you will probably encounter both rain and sunshine. That’s what makes it so beautiful! During the hiking season no month is more likely to be dry than any other, so we suggest you simply choose the dates that best fit your calendar.

     – What is a Scottish Summer like? The truth about our weather.

    Scotland’s Weather Forecast – 10 Best Resources.

    How far ahead do I have to book? Read More

    We would consider 8 weeks before travel as the absolute latest we can arrange it for you but for popular times of year (especially May) it will be necessary to book up to 6 months in advance. We always recommend you book as far ahead as possible – it’s never too early.

    How will I find my way? Read More

    We provide route notes and maps for you to follow during your hike, and the trails are well marked and quite easy to follow.

    Can I add an extra night at the beginning or end? Read More

    Yes, just ask us for this and we’ll be happy to arrange it.

    Can I have a rest day during the trip? Read More

    Yes, but this needs to be planned when you book. We can’t change all your reservations once you’ve started the hike.

    Can I skip days if I want a rest? Read More

    Since these are all point to point hikes skipping any day will require you make arrangements to travel to the next accommodation. This will usually require a taxi. Due to the geography of the Highlands with lots of lochs and glens this will be longer on some days than others.

    self guided walking holidays

    Hiking alongside Loch Lomond on the West Highland Way.


    How much do I have to carry? Read More

    Your luggage will be transferred between accommodations, so you only need to carry a daypack with your daily essentials. We include a comprehensive equipment list as part of your information.

     – The best footwear for hiking in Scotland.

    What to Bring on the West Highland Way.

    Can I bring my dog? Read More

    No. Unfortunately there are not many dog friendly accommodations along the route so we cannot offer this.

    I have dietary requirements - can you cater for me? Read More

    Yes. Please advise us at the time of booking so we can inform the accommodations who will make arrangements accordingly. Restaurants etc will have options for common dietary requirements such as vegetarian, vegan, gluten free.

    We don’t have enough time do the whole hike. Can you shorten it for us? Read More

    Yes. But the minimum length of trip we will offer you is 5 nights.

    Do you offer these trips for solo travellers? Read More

    No. The minimum group size is 2 people for self guided hiking. However, solo travellers are welcome on all our guided trips.

    self guided walking holidays

    Woodland section on the Speyside Way in the Cairngorms.


    What are the accommodations like? Read More

    The accommodations range from small guesthouses, Highland inns, small hotels and bed and breakfasts which will be of a 3/4 star standard.

    If you choose the upgraded accommodation option we will reserve the best available accommodation option in each location for you. This will generally mean 4 star rather than 3 star, or where we must use the same accommodation a superior room vs standard.

    On some itineraries there are also options to enjoy some nights in luxury hotels.

     – The Unexpected Charms of BnBs on the West Highland Way – Guest post from American hiker Brandi Willis Schreiber.

    Do I need to carry lots of cash? Read More

    No. Almost all shops, restaurants, pubs etc are able to take credit and debit cards so you only need to bring a little cash for incidentals. If you need more you can find the location of the nearest ATM as part of the trip information we will send you, and many shops offer cashback.

    Where will we eat? Read More

    Breakfast is included every day at your accommodation. Some accommodations can arrange a packed lunch for you if you request this when you arrive. There are also village shops where you can pick up supplies. For evening meals there are restaurants/pubs/hotels you can choose from and we provide recommendations as part of your trip info.

     – West Highland Way Food Guide – Best Eateries Along the Route.

    How do I book? Read More

    If you’re ready to book then you can do so online, or you can call (Tel UK: 01479 420 020 Tel US: 1-866-740-3890) or email us. We will take your details and a 25% deposit then start making the arrangements for you. Once everything is booked we will confirm your trip.

    How long will it take to get confirmation? Read More

    It depends. We have a team dedicated to working on these trips, so if there is good availability at the accommodations then it only takes a few days to book everything. If we need to look around lots of options for you or are very busy it may take a couple of weeks. Rest assured though that we will work as quickly as possible to secure your self guided adventure.

    Meet the Author: David Russell

    “I discovered the magic of the outdoors while studying Physics at the University of St Andrews. After graduating I decided to follow my dreams of freedom in the hills and rivers, and trained as an outdoor instructor. After several years of guiding with Wilderness Scotland I moved into the role of Adventure Consultant, but I still get out when I can to share my special places with adventurers from all walks of life.”

    View profileMore by David

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