Tailor Made Walking Holidays

Let us Plan and Book Tailor Made Walking Holidays in the Yorkshire Dales, North York Moors and the Lake District. We will plan a great route for you, send map/route details, book the hotels and arrange for baggage transfers.


Whether you know little about what to do and where to go and wish to use our own knowledge to build the best holiday for you and your party OR whether you simply do not have the time to sort it all out we will help. The walks are all Self Guided.

Things to consider when considering a Walking Holiday in the UK  Have a read here

What we provide

We have a high level of expertise in booking all sorts of walking holidays for different people; whether experienced walkers or novices. This is based on a lifetime of experience and knowledge of each area. We will…

  • Offer expert advice on the best options for you and your party
  • Source and book the accommodation (Guest House or Country Pub)
  • Provide a Baggage movement service (optional)
  • Include a pack with maps of the area, route notes & other information including where to eat and what to take.
Yorkshire Dales scenery

Below are our 2 most popular Tailor Made Walking Holidays. We call them our Tasters as they offer a great introduction to the Yorkshire Dales or Lake District

Example A. Yorkshire Dales Taster (3 to 6 days)

A fine introduction to the Yorkshire Dales with the walks taking you over rolling countryside and through limestone scenery with visits to small ‘Dales’ style villages and such iconic sites as Malham Cove, Gordale Scar, Littondale, Malham Tarn and the waterfalls at Cray

Day 1. Arrive at Grassington

Day 2. Grassington to Kettlewell/Buckden (7/11 miles)

Day 3. Kettlewell/Buckden to Arncliffe (6/10 miles)

Day 4. Arncliffe to Malham (6/10 miles)

Day 5. Malham to Grassington (6 miles)

There are options to reduce this walk by a day or better still spend more time and a couple of nights in one or more of the locations.

Example B. Lake District Taster (3 to 6 days)

Walking from the popular town of Keswick in the Northern Lakes this splendid walk visits Buttermere and Borrowdale with low level valley walking as a possibility or a more energetic option over the higher ground and fells.

Day 1. Arrive at Keswick

Day 2. Keswick to Buttermere (8/11 miles)

Day 3. Buttermere to Rosthwaite (Borrowdale) (6/12 miles)

Day 4. Stay at Rosthwaite (6/11 miles)

Day 5. Rosthwaite to Keswick (5/7 miles)

The options on this walk are endless with low level sites such as Ashness Bridge, Honister Pass and Newlands enroute for some whilst the energetic can take on such fells as Haystacks, Scafell Pike and Grasmoor.

For other examples of holidays people have booked with us just click here.

Request a Tailor Made Walking Holiday

There is a short contact form at the foot of this page. If you could fill it in that would help us decide what type of holiday would be best for you, the more information you give us the more likely we are to get something that is best for you.  The information that you have provided will be used only in preparing an itinerary for you.

Alternatively call me on 07824 304060 for a friendly chat or via email at jonathan@where2walk.co.uk.

We will email you a sample itinerary and quote within 48 hours (if you have not received it please do check your spam folder,)

Booking enquiry form

Preferred Daily Mileage (estimate)(required)

Preferred room type(required)

Do you want a baggage movement service(required)

  • Helen says:

    Just a note to thank you very much for all your help and organisation for our recent Dales walking trip. It was a great success enjoyed by everyone.
    The route was excellent and we all (apart from Jill, who you kindly taxied back to Ingleton!) particularly enjoyed the last day, especially in that we could see from the top of Whernside where we had walked for the previous four days.
    The accommodation was excellent and we were made to feel very welcome at all the venues.
    The weather was hot but we really couldn’t complain! It just meant that the first pint of beer each evening was very much appreciated.
    I used the OS app on my phone for the first time. You probably don’t approve but it was excellent for the few occasions of path indecision.
    Back to normality this week and work but so glad to have finally got away.

    Very best wishes


  • Ailie says:

    Two walkers and one semi-walker with six days available to walk. Oh! and we wanted a half day off together somewhere.

    That was Jonathan’s brief and he put together a really super programme along the Cleveland Way, using taxis, buses and Sherpa Van to move us (and our luggage) along in between stretches, including suggesting shorter routes for our semi-walker. We had three days on the glorious N. Yorkshire moors and three days along the tops of the cliffs Saltburn and Scarborough. With a happy half day in fascinating Whitby.

    He also provided clearly marked maps for us and arranged taxis where necessary. It was brilliant and we had a really super holiday.

    Thank you too, Jonathan, for your patience in dealing with my endless queries before we set off.

  • Nadia says:

    We have just had six great days in the Lake District. As visitors to the UK we relied on Jonathan’s knowledge and expertise. We were very Impressed with the walks and perfect accommodation that Jonathan organized.

    He also provided us with alternative routes if the weather forecast was bad, which was really very helpful.

    Thank you Jonathan and where2walk for a wonderful holiday.

  • Alison Mattinson says:

    We had a lovely walking holiday in The Lakes. Your routes took us to some beautiful areas that we hadn’t explored before. The walk up to Sprinkling Tarn was my favourite and it was stunning in the glorious sunshine with snow on the mountain tops. All the arrangements were problem free and the hotels you picked for us were perfect. Thank you so much.

  • Natalie McCarthy says:

    I can’t thank you enough for our fabulous 4 days in the Yorkshire Dales. Your suggested route was incredibly diverse and just stunning passing through parts of the Dales and Pennie Way. I loved how each day included time on the flats beside meandering rivers, time through farmland, forests and over the Dales with incredible mountain scenery. Each night in a different pub was just perfect and I couldn’t pick which was best – they were all wonderful, homely, friendly and the food was fabulous. Luggage transfer each day was seamless. Maps and direction were clear.

    I am a keen hiker who always spends holidays walking and have been fortunate to walk for months on most continents around the globe. Holidays usually are preceded by enormous research and reading. For this holiday, I was short of time and was seeking a short romantic break onto the end of a trip from Australia to the UK for a family wedding. It’s my first experience using a business to plan and book my walk, also my first time using luggage transfer. I couldn’t be happier with the result and it far exceeded my expectations. Thank-you Jonathan!

    Oh and I have walked in the Lakes, Scotland, Snowdonia’s and lots in Northumberland. I can’t quite believe I overlooked Yorkshire Dales for so long. This area is wonderful.

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