Tailor Made Walking Holiday

Let us Plan and Book a Tailor Made Walking Holiday in the Yorkshire Dales, North York Moors and the Lake District.

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 but we will provide suitable maps with the routes marked on.

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

What we organize

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 advice on the best options for you and your party
  • Source and book the accommodation (Guest House or Country Pub)
  • Include a pack with maps of the area & notes on the route and what to see
  • Provide a Baggage movement service (optional)

Below are our 2 most popular Tailor Made 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.

Book a Tailor Made Walking Holiday

We will also plan & book your long distance walk on the Dales Way, Cumbria Way,Cleveland Way or the Bracken Way click here

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 contact us 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,)

When you are ready to book read our Booking Conditions and fill in the booking form below


Booking enquiry form

Comments Leave your comment

  1. Judy Mullen says:

    Jonathan Smith tailor-made our recent six day hike in The Lake District National Park and the Yorkshire Dales to suit our request to cover some hiking trails in both areas and it was very enjoyable. We were part of a group of four – two couples and enjoyed some terrific day walks and accommodation at B & B’s and country pubs along the way. Where2Walk organised the walking routes, accommodation, transport with local taxi companies to take us, our luggage or both from town to town which meant we could hike with day packs only. The maps provided detailed routes to follow and were relatively easy to follow, although we may have benefitted from knowing a few more navigation tools!
    The highlights were stunning town of Grasmere with the river meandering through the town at the back of our accommodation, the specialist gingerbread shop and Tweedies pub where we ate some terrific meals after a strenuous day’s hiking. The towns of Ambleside, Windermere and Giggleswick were interesting to explore and offered some good meal options and fabulous pubs full of dogs and interesting people. The Station Inn Hotel at Ribblehead was unique and located near the famous viaduct bridge which the perfect backdrop to the pub’s dining room. The Hart’s Head Hotel in Giggleswick was a great place to stay to finish our trip and Jonathan saved the day by providing transport to Manchester Airport in the middle of the night.
    Coincidentally I had also read James Rebanks’ “The Shepherd’s Life: Modern Dispatches from an Ancient Landscape” which I strongly recommend to anyone contemplating a hike in The Lake District as he paints the picture of the landscape and the farming practices so vividly.
    I would highly recommend the services of Where2Walk to anyone interested in a fabulous holiday hiking in this part of the UK.
    Judy Mullen, Melbourne Australia.

  2. Barbara Parmenter says:

    My friend and I just returned from an 8-day walking holiday in the Yorkshire Dales arranged by Jonathan Smith at Where2Walk. We had never done a trip where we walk from place to place, and wanted to try. It turned out to be an absolutely wonderful trip, exactly what I had hoped. We didn’t know anything about the Dales, so we left the route-planning all to Jonathan and the routes each day were lovely. We had specified about how much we could walk each day (6-12 miles), and luckily for us, Jonathan also planned so we sometimes spent a couple nights in one place (with suggested walks the 2nd day around the area). This proved to be important for us, giving us some days we could rest a bit. And a shout out to the people of Yorkshire who were so welcoming and friendly. The owners and staff of the accommodations Jonathan had arranged were without exception amazingly friendly and helpful. Jonathan was very responsive both before the trip and the few times during it when I had some questions. Thank you for that, it was very reassuring.

    One important note – you definitely need to be able to use a topographic map and on occasion, a compass. Don’t go walking up over the moors without those skills. I felt very confident but my friend said she would have been lost without me, and you are frequently out of cell service areas while walking. The OS maps that Jonathan provides are excellent.

    Finally, we read James Rebanks’ “The Shepherd’s Life: Modern Dispatches from an Ancient Landscape” during our trip. Although it is about the Lake District, reading it gave us a much deeper understanding and appreciation of sheep farming, the knowledge and skills that it entails, and the long history of shepherding culture in northern England. Great book especially when it was mostly just us and the sheep each day.

    Thank you, Jonathan, for a really wonderful experience.

  3. 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.

  4. 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.

  5. 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.

  6. 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.

Leave a Reply