Holiday Packages
All our Standard Itineraries include:
- Hand-picked accommodation in B&Bs / guest houses / inns / small hotels
- En-suite facilities where available
- Breakfast
- Daily baggage transfers from our own team of local drivers
- All booking fees
We will also endeavour to include all these in any custom itinerary you wish to build for this walk.
Day 1: Helmsley to Kilburn (9.9m)
Day 2: Kilburn to Osmotherley (14m)
Day 3: Osmotherley to Clay Bank Top (10.8m) (personal transport to/from Great Broughton or Chop Gate)
Day 4: Clay Bank Top to Kildale (9.3m)
Day 5: Kildale to Slapewath (10m)
Day 6: Slapewath to Staithes (12.9m)
Day 7: Staithes to Whitby (11.1m)
Day 8: Whitby to Ravenscar (10.1m)
Day 9: Ravenscar to Scarborough (North) (10.2m)
Day 10: Scarborough (North) to Filey (10.2m)
£1,390 per person (based on 2 people sharing)
Day 1: Helmsley to Osmotherley (21.5m)
Day 2: Osmotherley to Kildale (20.1m)
Day 3: Kildale to Staithes (22.9m)
Day 4: Staithes to Ravenscar (21.2m)
Day 5: Ravenscar to Filey (2.4m)
£790 per person (based on 2 people sharing)
Day 1: Helmsley to Osmotherley (21.5m)
Day 2: Osmotherley to Kildale (20.1m)
Day 3: Kildale to Slapewath (14.6m)
Day 4: Slapewath to Runswick Bay (15.8m)
Day 5: Runswick Bay to Ravenscar (18.3m)
Day 6: Ravenscar to Filey (20.4m)
£910 per person (based on 2 people sharing)
Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top personal transport to/from Great Broughton/Chop Gate (11m)
Day 4: Clay Bank Top to Slapewath (19.3m)
Day 5: Slapewath to Runswick Bay (15.8m)
Day 6: Runswick Bay to Ravenscar (18.3m)
Day 7: Ravenscar to Filey (20.4m)
£1,030 per person (based on 2 people sharing)
Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top personal transport to/from Great Broughton/Chop Gate (11m)
Day 4: Clay Bank Top to Newton under Roseberry (14.3m)
Day 5: Newton under Roseberry to Staithes (19.3m)
Day 6: Staithes to Whitby (11.1m)
Day 7: Whitby to Cloughton (16.2m)
Day 8: Cloughton to Filey (15.9m)
£1,140 per person (based on 2 people sharing)
Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top personal transport to/from Great Broughton/Chop Gate (11m)
Day 4: Clay Bank Top to Great Ayton (14.3m) leaving the path at Cockshaw Hill
Day 5: Great Ayton to Saltburn (14m)
Day 6: Saltburn to Runswick Bay (11.3m)
Day 7: Runswick Bay to Whitby (8.2m)
Day 8: Whitby to Cloughton (16.2m)
Day 9: Cloughton to Filey (15.9m)
£1,290 per person (based on 2 people sharing)
Day 1: Helmsley to Kilburn (9.9m)
Day 2: Kilburn to Osmotherley (11m)
Day 3: Osmotherley to Clay Bank Top (10.8m) (personal transport to/from Great Broughton or Chop Gate)
Day 4: Clay Bank Top to Kildale (9.3m)
Day 5: Kildale to Slapewath (10m)
Day 6: Slapewath to Staithes (12.9m)
Day 7: Staithes to Whitby (11.1m)
Day 8: Whitby to Robin Hoods Bay (6.7m)
Day 9: Robin Hoods Bay to Cloughton (9.5m)
Day 10: Cloughton to Scarborough (South) (7.4m)
Day 11: Scarborough (South) to Filey (8.5m)
£1,490 per person (based on 2 people sharing)
Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top personal transport to/from Great Broughton/Chop Gate (11m)
Day 4: Clay Bank Top to Great Ayton (14.3m) leaving the path at Cockshaw Hill
Day 5: Great Ayton to Saltburn (14m)
£810 per person (based on 2 people sharing)
Day 1: Saltburn to Runswick Bay (11.3m)
Day 2: Runswick Bay to Whitby (8.2m)
Day 3: Whitby to Ravenscar (10.1m)
Day 4: Ravenscar to Scarborough (North) (10.2m)
Day 5: Scarborough (North) to Filey (10.2m)
£780 per person (based on 2 people sharing)
* All headline holiday prices are shown per person, based on two people sharing.
** Prices may vary depending on availability, time of year, number of travellers and room type. Please enquire for a personalised quote.
Baggage Transfer
Baggage Transfer is automatically included in the price of all our Walking Holiday packages.
These prices are for anyone planning their own holiday and just need bags moving from one stop to the next.
1 bag: £38 per bag per day
2 bags: £22 per bag per day
3 bags: £20 per bag per day
4+ bags: £17 per bag per day
*Prices may vary depending on route, mileage and direct road access. Please complete the enquiry form for a personalised quote.
Note: If you are booking accommodation in an Airbnb, you must ensure that there will either be someone available to take collection/delivery of your bags or that they have appropriate, secure storage in the event that the proprietor is absent.
26 Replies to “Cleveland Way”
I, together with two friends, have just completed seven days walking the Cleveland Way. We started at Helmsley and, because of work commitments, finished our walk at Robin Hood’s Bay. Apart from some heavy rain on the first morning the weather was generally kind to us, which made our walking a lot more pleasurable.
The walking is fairly easy going although, as others have noted, there are a number of steep ascents and descents where the route crosses some steep sided river valleys and care is needed on the wet and slippery rocks. The route offers a nice contrast between the moorlands and uplands of the North Yorkshire Moors and the second half along the spectacular cliffs of Yorkshire coast. Our favourite stages were along the escarpment from Osmotherley to Clay Bank Top and the coastal section from Runswick Bay to Robin Hood’s Bay, where Staithes and Whitby were an absolute delight.
As always, Annette and her team at Brigantes, organised our walk superbly. The accommodation was generally very well suited to our needs ie. a friendly and welcoming atmosphere, hot water and a comfy bed, good food and some nice beer. The majority of the places we stayed in were actually on the Cleveland Way. Another bonus is the fact that the 1.5 miles between Sandsend and Whitby is the longest stretch of road walking on the whole route. Annette has now organised walks for us on the Pennine Way, the Coast to Coast Path, the Swaledale Way and the Pen y Ghent Circular, each one to the same high standard. Our luggage is always picked up after 9.30 am (not in the middle of breakfast at 8.30!) and delivered before our arrival. We will certainly be looking at using Brigantes next year, perhaps on the Alternative C2C route.
First a note about the service provided by Brigantes (I just used the bag transfer service for our group). First class as ever! The bags were at our destinations at the promised times and in good order. Thanks again to Annette and the team!
Our group thoroughly enjoyed the Cleveland Way. As others have mentioned, there are some steep climbs and descents, but that’s a part of the challenge. It should also be noted that there is also plenty of ‘easier’ walking by which to enjoy the Yorkshire countryside., which just gave and gave. We even got a 10 minutes Anglo Saxon History lesson at the Sutton Bank Visitors Centre (a very handy venue for a refreshments break). It’s difficult to get lost as the signposting is excellent and the paths are in good condition. Accommodation wise, very little in some places (Sutton Bank, Great Ayton, Osmotherley areas), but all that we did stay in were fine even if some are getting to be a little bit on the expensive side for a brief walking holiday stopover. Evening meals wise, no real shockers. I’d say the highlights were Bantam in Helmsley, the Golden Lion in Osmotherley and (bit pricey but bit of a treat) the Seaview in Saltburn. We finished off with a nice Italian (Cosa Nostra) in Whitby….but there’s always good fish and chips!
Due to time constraints, we finished our walk at Whitby (we will be back to complete the route to Filey!). We arrived there on Regatta weekend Saturday. Now, Whitby is a lovely place and very popular as a result. My goodness, it was a sea of humanity! If you don’t like crowds, plan this stopover carefully! There was a bit of a clue as to what to expect when I found no B&B availability when I was doing the bookings many months ago. Fortunately, I found one of the few self catering holiday homes that took a single night’s booking (Helin’s Cottage). This is in the centre of Whiby, is nicely presented but has a lot of stairs and there’s only one shower room (observations for info, not a complaint). In terms of transport, we had to get back to the Manchester area on a Sunday. We could have done it by train, but it would have taken most of the day! So for the first time, we arranged to leave our cars in Whitby for the week and head back to Helmsley via a bonus trip on the North Yorkshire Moors Railway and pick up the trusty 128 service from Pickering. By the way, the tourist info in Whitby were very helpful with information for long term parking (we managed to park on the Marina car park, very handy).
We have just returned from 8 days walking the Cleveland Way. The picturesque town of Helmsley, the start of the walk, is easily reached by public transport, train to Scarborough then bus to Helmsley. The walk begins through pleasant countryside, with stunning views over the Vale of Mowbray, then up into high, remote moorland. At Saltburn, the path follows the coast down to Filey, with beautiful sea views and quaint little towns and villages.We got to Robin Hood’s Bay on a sunny bank holiday Monday, a situation best avoided!
Overall, we found the walk quite challenging, with a lot of steep ascents and descents. The path is very clearly signposted and well surfaced in most places. We have used Brigantes on many occasions, and, as usual, the accommodation was good and the bags appeared and disappeared by magic.
My friend and I walked a ten-day meander around North Yorkshire, on no established long-distance routes and sometimes to quite out-of-the-way places (Constable Burton?). Brigantes couriered our luggage every day. Though I never met any of the drivers, I can wholeheartedly recommend Brigantes as a luggage courier service. Our bags were picked up promptly and deposited at our next destination early in the afternoon. One driver even carried our bags upstairs at a small hotel. Everything went very smoothly.
Thanks for your faultless organisation for us on the Cleveland Way and the Tabular Hills Walk. I had a great time on this memorable circuit
Thank you very much for the wonderful service transporting our baggage. We walked the Cleveland Way in May 2022 and our luggage was collected on time and always waiting for us at our destination. On our last day the cases were delivered to Filey before 12 noon, so that we could catch our train back to London from York.
We are very happy with the great service and will certainly use you again for a holiday in the future.
A wonderful six days (Oct 6 – 11, 2021) walking most of the Cleveland Way was made even better knowing we had the Brigantes team moving our bags each day. Excellent service as always (first used by us on the C2C in 1999 and on several occasions since). The variety of views and landscapes, coupled with fine Yorkshire weather, made the CW one of the best routes we have completed in the UK.
Just back from a wonderful holiday on the Cleveland Way, organised by Brigantes. Our accommodation was all very good – several days we said “This is the best one yet!” Luggage transfers were very efficient, and most days it was already in our rooms when we arrived, which we really appreciated after a long day of walking. The only day it was a bit late (and we arrived early that day!) we got a text from Annette telling us it would be a bit late. So we didn’t have to worry. I hope we can plan another walking holiday with Brigantes in the future.
I am just home from walking the coastal section of the Cleveland Way, from Saltburn to Filey. I have been hiking for almost 50 years, but this was the first time I’d used a company to arrange accommodation and baggage transfer. I can only say the service was faultless in all respects. Professional, courteous and prompt, Brigantes allowed me to enjoy wonderful walking reassured that my baggage was safe and my lodgings comfortable each night.
I have no hesitation in recommending Brigantes, and will certainly us their services again for my next trip. Many thanks to all at the company.
I walked the Cleveland Way in July 2021 and would recommend this route as a great way to explore the moors and coast of North Yorkshire. The way is well signposted and the route is easy to follow. The first few days walking are quite varied in terms of length and terrain, undulating through woodland and over moorland. The second half is quite different following the coast path between the different seaside towns and although still undulating it is flatter and less strenuous. On balance I found the moorland more interesting and varied than the coastal parts. Most of the accommodations were off the way but with the majority, but not all, offering lifts to avoid excessive road walking. Only one place was a significant diversion from the route and did not offer a lift. The quality of accommodation varied a bit, most were excellent with good size rooms and great breakfasts and only a couple either poorly located or having a very small room. The luggage transfer with Brigantes was very good with pick-up and delivery consistent on each day and always on time. I would recommend researching and booking evening meals/restaurants ahead of time as there can be limited availability, particularly in the seaside towns.
Just back from a six day crossing of the Cleveland Way with Brigantes taking care of our luggage. I can only echo all the other comments here. The service was superb. With one exception (Day 2 – Osmotherley to Great Broughton) our bags were always waiting for us and the exception was only due to us arriving at the hotel at 2pm. The bags arrived 20 minutes later. I was especially impressed to learn that Brigantes had an arrangement to allow them to deliver bags to Filey train station. This meant that we didn’t have to stay an additional night and our bags were ready and waiting for our trip home.
I’d have absolutely no hesitation in recommending Brigantes luggage transfer service and will be definitely using them again.
Thanks to Brigantes for arranging the accommodation and transport for our walk along the Cleveland Way. 110 miles in 7 days was a challenge for a 70 and 69 year old, but we could relax and concentrate on our walking in the knowledge that the logistics would be spot on. We have used Brigantes before and, God willing, will do so again.
Four of us (total age 262, well oiled walking machines) walked the Cleveland way this month. Booked it through Brigantes, whose organisation was faultless – all accommodation was fine, hosts were very personable, all baggage transfers completely efficient. Will certainly be happy to book further walks through Brigantes.
Despite walking ‘the wrong way,’ as everyone we met kept telling us, ie. heading north from Whitby, Brigantes gave an excellent service from my first enquiry to our last days walking. (We met a lot of other walkers by going this way round) The luggage transfers were magical, the route well marked and our accommodation varied and interesting with some delightful hosts.
Another very successful trip organised by Brigantes (last year I did the Pennine Journey). All the organisation ran extremely smoothly – B&Bs ranged from perfectly satisfactory to excellent and my bag was always waiting for me. The path is very clearly marked and the scenery spectacular. Would certainly recommend both the walk and Brigantes.
Used Brigantes for the second time, and very much last minute, doing the Cleveland Way, and also the Tabular Hills Walk to get back to Helmsley, which other companies would not include, and they were brilliant.Everything went according to plan, with the few tiny hiccups quickly sorted out. We will certainly use them again in future … as long as our elderly legs keep walking!
We finished the Cleveland Way from Runswick Bay to Filey,adding a leg from Filey to Bridlington. Used Brigantes for baggage transfer for the third time and as before, everything went very well. We now intend to use this service every year.
Once again we used Brigantes after the success of our previous walk doing the first half of the Cleveland Way, and once again Brigantes came up trumps transporting our bags down the coast from Saltburn to Scarborough. All our party of seven very well educated, though ageing walkers, had nothing but praise for Brigantes. Once again, we left our bags in reception at host hotel, and once again they were magically teleported to our destination, ready for our arrival. An excellent service throughout, from booking, communication and delivery. A beautiful walk from Saltburn to Scarborough aided and enhanced by great back up service, many many thanks. Trevor and chaps, May 2017.
Mother and Son Walking the Cleveland way in August 2016 (We’ve just come back) I can only agree with Trevor Thomas. We do thank Brigantes for having done such an excellent job. Having worked in tourism myself, I am quite much aware of all the odds that can happen! We had none! Accomodation and baggage Transfers worked out perfectly.
Thanks again and a big “hello'” from Hamburg.
Seven educated gentlemen walked the Cleveland Way between Sutton Bank and Saltburn, Apr-May 2016. We used Brigantes as our luggage transfer carriers and they were simply “Brilliant” in every respect. The communication whilst booking was superb, the detail provided was excellent, and the job itself was executed very very professionally. So much so, we never saw a driver, we simply left our bags in reception at our host hotel, to be ‘teleported’ to our destination, and were ready when we arrived. No idea how it happened, but it just did!!
Great job, will be definitely using Brigantes again
We loved the walk you helped us plan and walk. Everybody we met has been so enthusiastic about their bit of the country and the walk in particular. You have some good hosts. One of Anne’s favourites was Glenda Calvert at Pry House Farm, Keld.
Just to let you know that we thoroughly enjoyed our C2C this year (Ingleby Cross to Glaisdale). Many thanks for all your excellent arrangements on our behalf. We would highly recommend Park House and also Blakey Ridge. We’ll be back next year for the final stage.
We thought that you might like to know that we successfully completed the C2C, arriving home last Saturday, fit and well without one blister between us. We’d like to thank Brigantes for the wonderful service we received from you.Undertaking the C2C was an absolutely wonderful experience and we enjoyed every minute of it (well, maybe not finding ourselves a few miles along High Street instead of at Kidsty Pike – luckily our only route finding mistake) and would recommend it to anyone wanting a challenge – especially if they have their main luggage carried by a reliable company.
Just a quick thank you for the wonderful job you all did moving our bags. I can’t imagine at my advanced age carrying all of my gear again, so it’s a miracle to have a service like yours. We highly recommend Brigantes to everyone we meet, including your other services (we met a group using the camping accommodations…brilliant!).
I have been meaning to email you and thank you for our holiday back in May. Jane and I had a fabulous time and all our drivers and accommodation were fab. Thank you to Brigantes for such a memorable time.
Our praying didn’t help much as we had rain most days, but it was a wonderful experience. Thanks for all your organizing, especially as it was last minute, and thanks from Lori for the rides in the baggage train! We enjoyed the second half (mostly in Yorkshire) more, as the people and the environment were more real and down to earth (the Lake District was more commercial) Every evening we had wonderful experiences in B&B’s and pubs, the people, the food and the interesting brews.