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Cleveland Way Walking Holiday in
Yorkshire, Northern England
108 mile walking holiday through North Yorkshire Moors and along the Yorkshire coast.
This forms part of the England Coast Path, is one of our Coastal Walking Holidays in UK and Ireland, one of our Moorland Walking Holidays, one of our Northern England Walking Holidays and also one of our National Trail Walking Holidays.
Where in the UK is the Cleveland Way?
Cleveland Way Walking Holiday
in The North Yorkshire Moors and along the Yorkshire Coast in Northern England
from Helmsley to Filey
via Rievaulx Abbey, Whitby, Staithes, Robin Hood’s Bay and Scarborough
The Cleveland Way walking holiday is a 108 mile National Trail hike through the unspoilt countryside of the North York Moors in Northern England.
This walking trail is a great introduction to long-distance walking holidays and is suitable for every level of walking ability.
The Cleveland Way forms part of the England Coast Path and connects with the Yorkshire Wolds Way at Filey and with the Yorkshire Coast Path at Saltburn.
We offer 1 suggested itinerary for the Cleveland Way walking holiday:
- 12 day walking holiday, 108 miles
Please see details and prices below.
Our self-guided walking holidays are designed with your comfort and enjoyment in mind and can be tailor-made to your own personal requirements.
The routes are clearly way-marked to provide reassurance on your hiking vacation.
We use a selection of guest houses, inns or small hotels with en-suite or private bathroom to ensure you are well rested each night after a busy day hiking and sightseeing. Rest assured that all our accommodation walking holiday providers are hand-picked and offer you that famous British hospitality.
Special diets can be catered for, including vegetarian, vegan, and gluten free.
We organize the luggage transfer so your bags are at your next accommodation when you arrive. We try to get your bags delivered by 4pm, but this may be delayed due to road conditions.
Let’s Go Walking has developed one of the largest selection of walking holidays.
Our offices are staffed 9am to 9pm during our walking season (March to September) to ensure your walking holiday runs without a hitch.
All our walking holidays are self-guided and you must be a confident map reader and able to navigate from a compass bearing. The weather in the UK and Ireland can change quickly effecting visibility and underfoot conditions. It is important to carry a selection of clothing with you on your hike each day to cope with changing weather conditions. If you are not confident of completing any days walk, do not set out.
This walking holiday in the UK operates March to September and in either direction.
The daily distances are only a suggestion. If you would like to walk longer or shorter distances, we can arrange that too.
Our stated distances include mileage to the accommodation or pickup point and so may not agree with the guide book mileages.
Rest days can be taken in any location.
Why not combine this walk with a hiking tour in another part of the UK or Ireland. Our staff will be happy to advise on necessary transfers.
Online booking available.
A deposit of £85 per person is required to secure the booking, with the balance due 6 weeks before departure.
Optional extra days and accommodation upgrades can be added during the booking process online.
Please wait for the confirmation of your holiday before making final travel plans just in case your holiday is not available for your requested date.
Helmsley to Filey
12 day itinerary
10 days walking and 11 nights
Suggested Itinerary
| Day 1: | arrive Helmsley | |
| Optional Day | optional extra day in Helmsley | |
| Day 2: | Helmsley to Sutton Bank | 10 miles |
| Day 3: | Sutton Bank to Osmotherley | 12 miles |
| Day 4: | Osmotherly to Clay Bank | 11 miles |
| Day 5: | Clay Bank to Kildale | 9 miles |
| Day 6: | Kildale to Skelton | 13 miles |
| Day 7: | Skelton to Staithes | 11 miles |
| Day 8: | Staithes to Whitby | 12 miles |
| Optional Day | optional extra day in Whitby | |
| Day 9: | Whitby to Ravenscar | 10 miles |
| Day 10: | Ravenscar to Scarborough | 10 miles |
| Day 11: | Scarborough to Filey | 10 miles |
| Optional Day | optional extra day in Filey | |
| Day 12: | depart Filey |
12 day itinerary 11 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2025 | £1,430 | £2,519 | £2,739 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Cleveland Way Walking Holiday
Helmsley to Filey
Suggested Tour Duration:
11 nights, 10 days walking
Total Distance:
108 miles/175 kms
Min/max daily distance:
9/13 miles
Average Daily distance:
11 miles
Grading:
Easy to Moderate
Features:
North Yorkshire Moors, Rievaulx Abbey
North Yorkshire Moors Steam Railway
White Horse at Kilburn
Mount Grace Priory
Staithes
Whitby
This path connects with:
Yorkshire Wolds Way
Yorkshire Coast Path
Optional Accommodation Upgrades for
Cleveland Way
Can be added when booking online
Subject to availability Supplement per person per night
Filey
White Lodge Hotel
double/twin
£64.00
single
please ask
108 mile walking holiday through North Yorkshire Moors and along the Yorkshire coast.
This forms part of the England Coast Path, is one of our Coastal Walking Holidays in UK and Ireland, one of our Moorland Walking Holidays, one of our Northern England Walking Holidays and also one of our National Trail Walking Holidays.
What’s included
in your Cleveland Way Walking Holiday in The Yorkshire Dales and The Yorkshire Coast in Northern England
- accommodation at high quality guest houses, inns or small hotels on a bed and breakfast basis
- room with en-suite or private bathroom, tea and coffee making facilities
- daily luggage transfer
- support should there be any problems on route
- detailed itineraries
- OS 1:25,000 map
- guide book to The Cleveland Way
Optional Extras
for your Cleveland Way Walking Holiday in The Yorkshire Dales and The Yorkshire Coast in Northern England
- upgrade to the region’s most elegant, prestigious and famous hotels, where available
- transfers back to car or station
- parking facilities
- rest days
- inn to inn walks
What’s not included
in your Cleveland Way Walking Holiday in The Yorkshire Dales and The Yorkshire Coast in Northern England
- lunches and dinners
- travel insurance
- entrance to Rievaulx Abbey (English Heritage)
Lunches and Dinners
These are not included.
Evening meals
These are available at overnight locations, either at your accommodation or in the town/village.
Packed lunches
These can be provided by your accommodation or can be obtained from a local store, or cafe or inn along the route.
Holiday Travel Insurance
We require that you take out holiday insurance as Let’s Go Biking Ltd accepts no liability for the following:
cancellation, personal accident, illness, loss/theft of personal possessions and/or money, and any unforeseen circumstances, especially travel delays.
This is in addition to our existing
booking conditions.
Please contact us if you have any questions.
Our telephone Lines are open 7 days a week.
UK +44 (0)1837 880075
or +44 (0)207 193 1252
March to September 9am to 9pm
October to February 9am to 5pm
US +1 (646) 233-1541
New York 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
AUS +61 (02) 8006 0182
Sydney 10 hours ahead of UK time:
March to September 7pm to 7am EADT
October to February 7pm to 3am EADT
CAN +1 (647) 4786251
Toronto 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
or
Cleveland Way Walking Holiday:
How to get there
- By Plane to Humberside International Airport, Leeds Bradford or Manchester where we can arrange transfer to Helmsley
- By Car to Helmsley where parking is available
- By Train / Bus to Helmsley
108 mile walking holiday through North Yorkshire Moors and along the Yorkshire coast.
This forms part of the England Coast Path, is one of our Coastal Walking Holidays in UK and Ireland, one of our Moorland Walking Holidays, one of our Northern England Walking Holidays and also one of our National Trail Walking Holidays.
We offer National Trail walking holidays in England and Wales in the UK.
This is one of our categories of walking holidays.
- Cleveland Way
- Cotswold Way
- Cumbria Coastal Way part of the England Coast Path
- England Coast Path
- Glyndwrs Way in Wales
- Hadrians Wall Path
- Norfolk Coast Path part of the England Coast Path
- North Downs Way
- Offas Dyke Path in Wales
- Peddars Way
- Pembroke Coast Path part of the Wales Coast Path
- The Ridgeway
- South Downs Way
- South West Coast Path part of the England Coast Path
- Thames Path
- Yorkshire Wolds Way
We have moorland walking holidays in the UK in England, Scotland, Wales, Northern Ireland, and Ireland.
This is one of our categories of walking holidays.
- Cleveland Way
- Coleridge Way in Somerset
- Copper Trail in Cornwall
- Cumbria Way passes through the Lake District
- Dales Way
- Dartmoor Way in Devon
- Glens of Antrim on the Moyle Way in Northern Ireland
- Glyndwrs Way in Wales
- Hadrians Wall Path
- Hebridean Way in Scotland
- Herriot Way
- Isle of Man Coastal and Moorland Footpath
- Macmillan Way West
- Mourne Way in Northern Ireland
- Richmond Way
- Tarka Trail in Devon
- Two Moors Way in Devon
- West Highland Way in Scotland
- Wicklow Way in Ireland
- Yorkshire Wolds Way
We have Coastal Walking Holidays in the UK in England, Scotland, Wales, Northern Ireland, Ireland, Isle of Man, Isles of Scilly and the Channel Islands.
This is one of our categories of walking holidays.
- Arran Coastal Way in Scotland
- Causeway Coast Way in Northern Ireland
- Causeway Coast Way and Glens of Antrim in Northern Ireland
- Channel Islands
- Cleveland Way part of the England Coast Path
- Cumbria Coastal Way part of the England Coast Path
- Dingle Way in Ireland
- England Coast Path
- Fife Coastal Path in Scotland
- Great Gardens of Cornwall
- Great Gardens of Devon
- Guernsey, Herm and Sark in the Channel Islands
- Hebridean Way in Scotland
- Isle of Anglesey Coastal Path part of the Wales Coast Path
- Isle of Man
- Isle of Mull
- Isles of Scilly off the coast of Cornwall
- Jersey Coastal Footpath in the Channel Islands
- Kerry Way in Ireland
- Lecale Way in Northern Ireland
- Lleyn Peninsula, part of the Wales Coast Path
- Norfolk Coast Path part of the England Coast Path
- Northumberland Coast Path part of the England Coast Path
- Peddars Way and Norfolk Coast Path part of the England Coast Path
- Pembroke Coast Path part of the Wales Coast Path
- Rye to Ramsgate on England Coast Path
- Solent Way part of the England Coast Path
- Somerset Coast Path part of the England Coast Path
- South West Coast Path part of the England Coast Path
- Suffolk Coast Path
- Tarka Trail in Devon
- Wales Coast Path
- Yorkshire Coast Path part of the England Coast Path
- Cleveland Way
- Cumbria Way
- Cumbria Coastal Way, part of the England Coast Path
- Dales Way
- England Coast Path
- Hadrians Wall Path
- Herriot Way
- Isle of Man Coastal Path
- Leeds and Liverpool Canal Towpath
- Nidderdale Way
- Northumberland Coast Path, part of the England Coast Path
- Richmond Way
- St Cuthberts Way
- St Oswalds Way
- Teesdale Way
- Yorkshire Coast Path, part of the England Coast Path
- Yorkshire Wolds Way
