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Cleveland Way - CoastlineCleveland Way – Coastal section -self-guided

Self guided walking holiday along the stunning Heritage Coast

Duration: 7 days/ 6 nights
Grade 2 Grade 2 - Moderate
Price: £555.00

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Holiday Details

  • Total Distance - 53 miles
  • Duration: 7 days, 5 days walking
  • Grade: Grade 2
  • Maps and itinerary provided
  • 6 Nights B&B (Twin Share Basis)
  • Available for solo walkers
  • Luggage transfers
  • Loan of GPS for holiday
  • 24 hour emergency back up
  • 15% discount at Cotswold Outdoor
  • Holiday Options
  • Single room supplement - £240.00
  • Transfer back from Filey back to Saltburn-by-the-Sea (departure day) - £100.00
  • Solo Walker supplement - £280.00.00 (includes single room supplement) please call to book
  • GPS rental - £25.00

Cleveland Way – Coastal Section -self-guided

In 1969 the 109-mile Cleveland Way opened, this was the second National Trial in England and Scotland to open. The route is a walk of two halves. Starting in Helmsley on the edge of the North York Moors it crosses farmland, woods, and beautiful heather moorlands then following along the dramatic coast line finishing in the seaside resort of Filey.

The route for this trip will start at Saltburn, this will be the start of a wonderful coastal walk, wandering through pretty fishing villages, such as Staithes and Runswick before reaching Whitby the home of Captain Cook, this is where he learned his seafarer's trade. Whitby is also home of the great Whalebone Arch which is a reminder of the many men who went hunting for whale. In 1826 200 men were lost at sea when the Esk was shipwrecked in a violent storm.

You will pass through Robins Hood’s Bay before reaching the large seaside resort of Scarborough before finishing your journey in Filey.


Day 1 - Arrive Saltburn-by-the-sea
Day 2 – Saltburn-by-the-Sea to Staithes – 9 miles / 14 kms
Day 3 – Staithes – Whitby – 12 miles / 19 kms
Day 4 – Whitby to Robin Hood’s Bay – 7 miles / 11 kms
Day 5 – Robin Hood’s Bay – Scarborough – 14 miles / 23 Kms
Day 6 – Scarborough – Filey – 11 miles / 18 kms
Day 7 – Departure day



    Day : 1 - Arrive Saltburn-by-the-sea

    Overnight stay

    You will arrive into Saltburn the home of the Saltburn Cliff Lift which is one of the world's oldest water-powered funiculars.

    If you arrive by train the station will be a 10-minute walk or a short taxi journey to your first nights’ accommodation.

    Day : 2 - Saltburn-by-the-Sea to Staithes

    9 miles / 14 kms

    This morning after a hearty breakfast, you will be ready to start the day with an ascent up Hunt Cliff the start of this striking section of the Cleveland Way, coming to the highest point on the east of England, Rock Cliff.

    The trail then dips down into the quaint fishing village of Staithes, once one of the largest fishing ports on the North-East coast.

    Day : 3 - Staithes – Whitby

    12 miles / 19 kms

    After a short walk you will reach the remains of the harbour of Port Mulgrave at the base of the Rosedale cliffs. Little remains here these days other than the subtle hint of past industry. After a wander along the cliff tops is Runswick Bay, one of Yorkshire Coast’s prettiest villages. With its sandy beach which was once full of brightly coloured fishing boats is now a known for rock pooling, coastal walks and its amazing views.

    Passing through the fishing village of Sandsend a dramatic coast path leads onto Whitby, with its busy harbour, fossil filled cliffs and Whitby Abbey the inspiration for Bram Stoker’s Dracula.

    Day : 4 - Whitby to Robin Hood’s Bay

    7 miles / 11 kms

    Today will be a pleasurable day across the cliffs from Whitby to Robin Hood’s Bay with some spectacular views and scenery.
    Walking past the lighthouse and old radar stations of the 2nd World War you will reach Robin Hood’s Bay.

    Day : 5 - Robin Hood’s Bay – Scarborough

    14 miles / 23 Kms

    Today is a more strenuous day, however the scenery is magnificent with outstanding views which make it worth all your efforts.

    Leaving Robin Hood’s Bay, the path takes to the cliffs again on the steep climb up to the impressive point at Ravenscar. From here the walk will provide stunning views with a walk down to Heyburn Wyke through some pretty woodland. Climbing out of here you will follow the undulating path to the seaside town of Scarborough, with its vibrant entertainment, large sandy beaches and grand hotels.

    Day : 6 - Scarborough – Filey

    11 miles / 18 kms

    An easier day today but still with stunning view as the path hugs the coastline along the cliff tops.

    The trail ends at Filey Brigg a spit of rock jutting out into Filey Bay. You will see a rock sculpture marking the end of the Cleveland Way.

    With a final descent down onto the promenade and then up into the town into Filey for your overnight stay.

    Day : 7 - Departure day

    Filey has great railway and bus connections.

    If you would like a transfer back from Filey back to Saltburn-by-the-Sea (if you have left your car at Saltburn-by-the-Sea). There will be an extra charge for this (please see 'holiday' options on the right of page) and add this to your booking as you book your holiday.

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    A beautiful walk.

    31st Aug 2018 Anne Carruthers

    This was our third holiday with Shepherds Walk. Outstanding company to book travel with-all the details are covered and explained. Cleveland Way was a senic and at times challenging walk. Places visited were delightful-small coastal villages to larger seaside resorts. Anyone who enjoys walking will love this hike.

    a great coastal walk

    29th Jun 2019Andrew Johnson

    For lovers of coastal walks this is a must, whether it is your first walk with Shepherds or your next, this walk has all the attributes that coastal walkers love. The fine scenery, variety and first class accommodation backed by the excellent service I have come to expect from Shepherds made it a great choice.

    From the first to last day, excellent.

    7th Jun 2019A Johnson

    The variation is what makes this walk a must, coast, country lanes, woodland and lots of flora.


    (A) Bed and Breakfast accommodation (twin or double share basis).
    (B) Route map, guide book and trip notes specific to your trip, including
    emergency contact numbers.
    (C) Luggage transfers between accommodation.
    (D) 24 hour emergency back-up service.


    (A) Any additional transfers not mentioned in the dossiers.
    (B) Personal clothing and equipment.
    (C) Insurance
    (D) Lunch and Evening meals.
    (E) Single room option (if required, see single supplement)
    (F) Transfer from Filey to Saltburn-by-the-Sea on departure day (if required, see single supplement)


    The Shepherds Walks Representative will :
    B) Provide you with map and talk you through the route over the phone if you request this.
    C) Provide you with information relating to events in the area during your time there.
    D) Arrange the transportation of your luggage.
    E) Be available should you have any problems during your trip
    F) Meet you on departure day to provide transfers as necessary to your car if specified in your booking or itinerary.

    We are here to offer you the best holiday you could ever imagine and we aim to do this through the personal service that we offer.

    Make your holiday run smoothly – We are here for you. Our sole objective is for us to help you. We are here at any stage of your holiday and even in the planning stages. We tailor things to your requirements, not those of the masses.

    We don’t cut corners - We want to see you again and want you to speak highly of Shepherds Walks Holidays. This is why we are literally willing to go that extra mile. The information you receive at every stage will be clear and leave you asking no questions.

    We have personally walked all the trips we offer - We know exactly what you are going to embark on and can advise you on any aspects of your holiday over and well above what many of our competitors can.

    Press choose to walk with us – Shepherds Walks Holidays are asked to deliver a very high percentage of the trips for journalists in the region. When the Tourist Boards are approached by a journalist wanting to visit the area who do they ask to provide their holiday or take them out walking? Shepherds Walks.

    We have had press trips on all our routes and the articles speak for themselves.

    Protected Holiday - All our holidays are protected through the operation of a Trust Account.

    We are close at hand if you need us – We are a local business and if you need us at any time during your holiday just ask. If you are on a self guided trip we often will catch up with you, even over a drink one evening, just to make sure everything is going well. It’s better to iron out any little problems during your holiday, rather than hearing about them when you are back at home.

    We enjoy great relationships with your accommodation providers and they will help us to help you

    As we are literally on the doorstep we know the best places to stay. Often we will have block booked the best accommodation the previous year. We want our customers to stay in the best possible accommodation. As we know the proprietors personally and we liaise with them regularly they will go that extra mile to help us to help you whilst out on your route.

    That is why Shepherds Walks has won awards and has helped people relax and totally enjoy their visit to this wonderful part of the country. We are willing to go that extra mile!

    Do you move our bags for us on our walking holiday?

    Yes, we move your bags for you everyday. You just leave your main bag at your accommodation and we will move it for you, so it will be at your next nights accommodation waiting for you.

    You just carry your day pack.

    Your baggage allowance for the trip is one main piece of luggage which should be preferably either a backpack/rucksack or sports bag, and one small daypack. Try to travel as light as possible. It is best to avoid large solid hardtop suitcases as these cause difficulties on transfer vehicles etc.

    The larger piece of luggage will travel on the vehicle between accommodations and the daypack should be suitable for carrying any additional outer-layer clothing and items you will need on your walk during the day. As a general rule, we would recommend that your main piece of luggage shouldn't weigh more than 15 - 20 kilos.

    We are thinking of a self guided trip, what happens if we need to speak with you during our holiday.

    Before your holiday starts we will give you a 24 hour helpline number for us here at Shepherds Walks Holidays. If there is anything we can help you with during your holiday just give us a call and we can sort it out for you.

    We would rather sort any problems out during a trip and then you can get on and enjoy yourself rather than finding out there has been a problem at the end when it is to late.

    Don't forget we are here to give you the best holiday experience we can.

    Once I have booked when will I receive the final holiday info?

    You will receive all your final walk info by email approximately four weeks prior to departure. A hard copy of your holiday pack will be posted to you the following day, including your map, giving you plenty of time to go through all of the information before your departure. Anything you are not sure about, we are only a phonecall or email away!

    What type of accommodation will we be staying in - self guided trip

    The accommodation on the tours are in Inns, family-run hotels, and Bed and Breakfasts. We endeavour to provide en-suite accommodation.

    Can I add an rest day into my walking holiday?

    Yes you can at any point, just get in touch and we can discuss the best options for this trip.

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    © Shepherds Walks Holidays 2020
    Muckles Yard, Bridge Street, Rothbury, Northumberland, NE65 7SG

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