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North Yorkshire Coast & Country

Unearth the charm of North Yorkshire and its undulating moorland vistas from our perfectly situated base in Robin Hoods Bay, strategically positioned between the enchanting towns of Whitby and Scarborough.

  • Yorkshire

  • Half Board
  • Coast & Islands

    Landscape

  • May

    Jul

    Sep

  • Average group size: 10-12

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Moderate

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Walking grade

Grade 5

Trips comprise of day walks with plenty of ups and downs, some steep and rough ground will be encountered at times and walks averaging 7 miles with 650m of ascent / descent. Some holidays will cover longer distances on easier paths, others will be shorter walks but have more demanding ascents and terrain.  

Usual daily walks - Distance: 7 miles; Ascent/Descent 650m; Terrain: generally decent paths and tracks with some steeper sections; Walking Time: Day walks. 

The above statistics are generalisations of a day’s keys walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

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Classic Collection

Thoughtfully designed, meticulously planned, carefully graded, and expertly guided walking tours and hiking holidays along well-loved and off-the-beaten-track footpaths.

Overview

Holiday Highlights

  • Cleveland Way coastal walking to Whitby.
  • Visits to coastal villages such as Staithes, Sandsend and Whitby.
  • Climb the magnificent Roseberry Topping, one of the most recognisable landmarks in the North Yorkshire Moors (also known as “Yorkshire’s Matterhorn").
  • Conclude a walk in Staithes, one of the most picturesque harbour villages on the Yorkshire coast.
  • View the awe-inspiring Hole of Horcum, a vast natural amphitheatre carved into the landscape.

North Yorkshire's rugged cliffs and breath-taking heather moors, coupled with its lush green valleys, epitomise the true essence of natural splendour. Our journey is a visual feast, showcasing the diverse landscapes that make this region so enchanting. Coastal villages will serve as the backdrop for many of our day walks, including the historic gem of Staithes, the picturesque haven of Robin Hood’s Bay, the serene retreat of Sandsend and the Gothic masterpiece that is Whitby.

Embark on a picturesque walk along the famed Cleveland Way coastal path from Whitby directly to our hotel. Here, you'll encounter a quintessential seaside scene: vibrant beach huts, charming antique shops, inviting tearooms, lively bars, and of course, top-notch fish and chips. Yet, amid the seaside allure, lies the enigmatic legend of Dracula, adding a touch of Gothic intrigue to the town. Feel the thrill as you explore the fishing hamlets and towering cliffs on the outskirts of Robin Hood’s Bay and the sprawling moors.

Another day will lead us further up the coast from Sandsend, on a cliff top journey offering stunning vistas, culminating at the delightful Runswick Bay and Staithes harbour. With its narrow alleyways, clustered red-roofed houses, and an inviting selection of tea shops and traditional pubs, Staithes provides the perfect place to relax after a day's walking.

The remarkable variety in scenery, coastal and inland walks, coupled with the rich tapestry of history and interest woven throughout, ensures that every avid walker will find themselves captivated by this expedition.

  • En suite three-star hotel accommodation on a half board basis
  • All local transport required for the itinerary by private coach
  • Services of a Classic Tour Leader
  • Entrance fees (unless otherwise specified)
  • Personal expenses (such as your bar bill)
  • Lunches
  • Discretionary tips
  • Optional excursions
  • Travel insurance

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet

Tour Codes

72225

Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Your Itinerary

Day 1

Arrival day

Meals

Dinner

Accommodation

Independent travel to the Victoria Hotel in Robin Hoods Bay. Check in is from 3pm. Meet your tour leader at approximately 6.30pm in the hotel for a briefing before dinner.

Day 2

Sandsend to Robin Hoods Bay via Whitby

Meals

Breakfast & Dinner

Accommodation

  • Time

    4 hours

  • Distance

    10.1 miles

  • Ascent/Descent

    180/117m

Today’s walk along the Cleveland Way National Trail features some of the most spectacular coastal scenery in England, combined with visits to two of the region’s most charming seaside towns. We begin in Whitby, an atmospheric town steeped in history. With its bustling harbour, narrow cobbled streets, and the famous 199 steps leading up to the dramatic Whitby Abbey, the town offers plenty to capture the imagination.

The route then follows the clifftop coastal path, offering sweeping views of the North Sea and the rugged coastline, before descending into Robin Hood’s Bay. This picturesque fishing village is a true gem, with its red-roofed cottages clinging to the steep hillsides. Its rich smuggling history and maze of narrow alleyways make it a fascinating place to explore and a memorable end to the day’s walk.

Day 3

Kildale to Slapewath via Captain Cook Monument & Rosemary Topping

Meals

Breakfast & Dinner

Accommodation

  • Time

    4.5 hours

  • Distance

    10.6 miles

  • Ascent/Descent

    474/547m

Today’s walk on the Cleveland Way National Trail is filled with iconic landmarks and breath-taking scenery. We begin by visiting the Captain Cook Monument, an impressive obelisk erected in 1827 to honour the famous explorer. Standing proudly above the landscape, it’s a memorable start to the day.

Our next highlight is the magnificent Roseberry Topping, one of the most recognisable landmarks in the North Yorkshire Moors. Rising in isolation from the surrounding Cleveland Hills, its distinctive shape has earned it the nickname “Yorkshire’s Matterhorn.” The climb to its 320m (1,050 ft) summit is rewarded with a panoramic view stretching across the moors and surrounding plains.

Continuing east, the route takes us through Guisborough Woods, the longest section of forestry on the Cleveland Way. Here, the trees part to offer glimpses of the plain below and spectacular views over Guisborough from Highcliff Nab. The day ends with a descent into Slapeworth, where we conclude this section of the trail.

Day 4

Sandsend to Staithes via Runswick Bay

Meals

Breakfast & Dinner

Accommodation

  • Time

    4.5 hours

  • Distance

    8.8 miles

  • Ascent/Descent

    350m

Today’s walk on the Cleveland Way National Trail begins in Sandsend, following the coastline past the small community of Kettleness, whose original village dramatically slipped into the sea in 1829. The route continues along scenic clifftop paths to Runswick Bay, where tide permitting, we can enjoy a leisurely stroll along the beach, soaking in the tranquil atmosphere of this beautiful stretch of coast.

We then return to the cliffs and follow the trail northwards, eventually descending into Staithes, one of the most picturesque harbour villages on the Yorkshire coast. With its narrow alleyways, clustered red-roofed houses, and an inviting selection of tea shops and traditional pubs, Staithes provides the perfect place to relax and conclude today’s walk.

 

Day 5

The Hole of Horcum

Meals

Breakfast & Dinner

Accommodation

  • Time

    4.5 hours

  • Distance

    8.3 miles

  • Ascent/Descent

    666/725m

Today we step away from the Cleveland Way National Trail to discover some of the most remarkable landscapes and landmarks of the North Yorkshire Moors. Our journey begins at the awe-inspiring Hole of Horcum, a vast natural amphitheatre carved into the landscape. According to local legend, this dramatic feature was created by a giant, and standing on its edge, it’s easy to see why such stories endure.

We continue on to Levisham, a charming picture-postcard village nestled in the moors, perfect for a peaceful pause. The walk also brings us to the Skelton Tower, a medieval-style tower perched high above the valley, offering breath-taking panoramic views. From here, we can enjoy a bird’s-eye view of heritage steam trains making their way through the moorland below - a sight that beautifully blends natural grandeur with historic charm.

Day 6

Departure day

Meals

Breakfast

Independent departure from hotel after breakfast. Check out of the hotel is by 11am. 

We hope you have enjoyed your holiday and look forward to welcoming you on another soon. 

Departure dates for your selected tour

Travel Details

Private coach transport to and from the trailheads, is included.  

Nearest railway and bus stations: Whitby (6 miles) or Scarborough (16 miles). 

Accommodation

Accommodation information

Below is the accommodation featured on this holiday across all departure dates. Please refer to the Itinerary for more detail about each night's accommodation for each departure date.

Victoria Hotel, Robin Hoods Bay

Boasting stunning cliff-top views over Robin Hood’s Bay, this grand four-star Victoria Hotel is on the edge of the North York Moors. The hotel offers homemade food, elegantly decorated bedrooms, Osborne's Restaurant & Lounge Bar and The Loxley, a traditional Yorkshire pub. Due to the nature and age of the building, there is no lift in the hotel and bedrooms may be split between floors. If you require help with your luggage, hotel staff will be more than happy to help you. 

Light and elegant, the rooms all provide a flat-screen TV, free Wi-Fi, free tea and coffee, Nespresso coffee machine and complimentary mineral water. Every bedroom has a private bathroom with complimentary luxury toiletries, a hairdryer and bathrobes.

Please note that your room may be located in the main hotel building or in the newly refurbished rooms in 'The Captain's Quarters' building located just a few steps away from the main hotel entrance. These rooms all have the same style and elegance of the rooms located in the main hotel building. 

The hotel has limited free parking, exclusively for residents on a first come, first served basis. Directly opposite the hotel there is a Pay & Display car park, with another large car park approximately 200 metres from the hotel. In the event you should need help with your luggage from the car parks, please let the Reception staff know and they we will assist you in their Hotel Victoria electric buggy.

Trip Information

All the details you need

Holiday Grade

Trips comprise of day walks with plenty of ups and downs, some steep and rough ground will be encountered at times and walks averaging 7 miles with 650m of ascent / descent. Some holidays will cover longer distances on easier paths, others will be shorter walks but have more demanding ascents and terrain.  

Usual daily walks - Distance: 7 miles; Ascent/Descent 650m; Terrain: generally decent paths and tracks with some steeper sections; Walking Time: Day walks. 

The above statistics are generalisations of a day’s keys walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

Walks & Excursions

Local Transport Costs

In the holiday cost, we have included all local transport expenses related to the advertised activity programme for your convenience. If there are additional visits or excursions to enrich your experience, you can choose to participate and cover the costs locally. Depending on the itinerary, local transport may involve a mix of private hire coaches, taxis, local buses, and ferries.

Optional Excursions

At your destination, you may have the option to book various local excursions and activities through a local operator. It's important to note that we are not involved in these activities or excursions, and we do not operate, supervise, or control them in any way. Your contract will be directly with the local activity supplier, and we bear no responsibility for their actions or omissions.

Spending Money

Holiday Budgeting

When budgeting for your holiday, you will need to consider drinks, non-included entrance fees, optional excursions you may choose to participate in locally and any souvenirs or additional services such as laundry. 

Tipping

In your holiday price, we've included tipping for our local suppliers, covering hotel and restaurant staff, local guides, and drivers. Should you wish to make an extra contribution for a specific service, this should be given directly to the recipient at your discretion.

Tour Leaders & Local Guides

Tour Leaders

Your tour leader plays a crucial role in enhancing your holiday experience, and they share your passion for exploring the world on foot. In addition to being resourceful and organised they are also well-travelled and deeply enthusiastic about showing you new destinations.  Your tour leader takes care of all the local administration, ensuring you can fully enjoy your holiday without worrying about the logistics. While leading group holidays, they always keep in mind that each group is composed of individuals. Each tour leader brings their unique style, talents, and professional background to the table. Rest assured, they are all trained, qualified, experienced, and dedicated to making your holiday as enjoyable, interesting, and inspiring as possible. Remember, your leader, while on holiday, is your first port of call for any issues, ensuring a smooth and worry-free experience for you.

Leader's Evening Briefing

Each evening, your tour leader will meet with you to review the programme for the next day. This is your chance to discuss details and ensure that the planned activities align with your walking ability. If you have any concerns about clothing or equipment, feel free to bring them up during this discussion. If, for any reason, you prefer not to participate in the organised group programme, please inform your leader. Your preferences are important, and your leader is there to make sure your experience aligns with your expectations.

Your Travel Details

Personal Details Check

To ensure the accurate administration of your holiday arrangements, kindly verify that the personal details we have for you are current and correct. Confirm that you've given us all the necessary information for securing your travel and accommodation. Please review your passport details, date of birth, and any other pertinent information crucial for the management of your holiday.

Additionally, please make us aware of any dietary allergies or intolerances you may have. Your well-being is important to us, and this information will help us make appropriate arrangements for your meals during the trip.

You can access and update the provided information or add missing details through the "Manage My Booking" feature on our website at www.rambleworldwide.co.uk. Alternatively, reach out to our Sales and Reservations team at +44 (0)1707 331133. Upon receiving your booking confirmation, promptly check the details. Your cooperation ensures a seamless and enjoyable holiday experience.

Meals

This tour is on a half board basis. Breakfast and evening meals are taken in the hotel restaurant, which offers a menu of locally sourced, freshly prepared dining options.  

Footwear & Kit List

Footwear

Lightweight waterproof walking boots with a good, moulded sole (such as Vibram or similar) and a deep tread and which provide ankle support are strongly recommended and may be essential for some walks.

General Kit List

Outdoor activities are always safer and more enjoyable if you are prepared.

If you have not travelled with us before the following list might be of use:

  • Waterproof jacket (Goretex or similar) and trousers
  • Lightweight quick-drying trousers
  • Walking T-shirt/shirts
  • Walking socks
  • Fleece or jumper
  • Sun hat, sunglasses, lip salve and sun block
  • Warm hat and gloves (if appropriate)
  • Swimwear & towel (if appropriate)
  • Day sack (this should be able to carry all you would need for the day's activity)
  • Day sack liner
  • Water bottle - at least 1 litre capacity (more than 1 bottle may be required)
  • Basic first aid kit
  • Lunchbox
  • Walking poles (should you find them useful)
  • Sit mat

This list is not exhaustive, and every walker is different and may have their own preference.

Travel Documents Checklist

Documents and Information to take with you:

  • Holiday money
  • Credit or debit cards (and separate details of who to call if lost)
  • Car parking ticket and car park directions (if prebooked)
  • Coach or rail travel tickets (if prebooked)
  • Holiday booking confirmation document
  • Travel insurance details (if applicable)
  • Details of any medical condition or allergy your holiday leader should know about

Maps, Guidebooks & Other Information

Maps, Guidebooks & More

The walks mentioned above are covered by the following maps:

Ordnance Survey Explorer 1:25,000 Series

OL26 North York Moors Western Area

OL27 North York Moors Eastern Area

The Map Shop

If you cannot find the maps or books locally, we recommend:

The Map Shop
5 High Street
Upton upon Severn, Worcs
WR8 0HJ
England

Tel: 01684 593 146
Website: www.themapshop.co.uk

If you key many of the local places mentioned in this holiday fact sheet into YouTube, you will find a vast array of spectacular footage of the area.

Weather

You may wish to look at the following websites for an idea of the climate in your destination; BBC weather or MyWeather2. 

Staying Healthy On Holiday

Health requirements in destination can change, and it's crucial for you to take responsibility in staying informed. Ensure that you consult a professionally qualified source and comply with any health requirements at least 6 to 8 weeks before your departure. Your GP can provide advice on vaccinations. Stay proactive about your health preparations to ensure a safe and enjoyable travel experience.

Health Advice for United Kingdom

No compulsory immunisations are required for holidays in the UK although you should be up to date with the usual immunisations recommended for life in Britain. Tetanus immunisation is recommended.

Further Travel Advice

For further advice please visit:

You might wish to take a small bottle of antibacterial hand gel with you for times when you're unable to wash your hands.

Travel Insurance

It’s a condition of booking that you obtain adequate travel insurance, from a reputable provider, to undertake the holiday, including UK trips chiefly due to the cancellation element of cover.

The policy must cover the period from the date of booking to the last day of your trip and should include, as a minimum, cover for: medical expenses, mountain rescue including helicopter rescue, death, repatriation, cancellation and curtailment and shall not have exclusion clauses limiting cover for the activities you will partake in on your trip, including altitudes reached in the holiday arrangement. It is your responsibility to check that your policy is adequate for the nature and destination of the holiday booked.

Once you have obtained your travel insurance, please provide us with the name of your travel insurer, the policy number and the insurer’s 24 hour emergency assistance number.

In the event that you fail to obtain suitable travel insurance we shall not be liable for any costs incurred or claims made against us due to your failure to comply with this term.

If travelling outside the UK you must carry proof of insurance with you and produce it if reasonably requested to do so by RWH Travel staff, tour leaders or suppliers. No refunds will be made should you be excluded from the walking programme through being uninsured or you being unable to demonstrate that you are insured.


Personal Safety

The UK Foreign, Commonwealth & Development Office is your go-to for the latest info on security, local laws, and the nitty-gritty of passports and visas at www.gov.uk/travelaware. Make sure to take a quick peek at the current advice for your upcoming destination—it'll only take a few minutes.

When you're out and about, stay aware of your surroundings. Take smart precautions with your credit cards and passport, and maybe tone down the flashy accessories. Less is more, especially when it comes to carrying cash—just enough for the day will do. Consider using a money belt for that extra layer of security. Stay alert, stay safe, and make the most of your travels!

Cultural Awareness

Responsible Travel

We are dedicated to promoting responsible travel practices that prioritise the well-being of both the environment and local communities. We believe in the transformative power of travel and aim to minimize our ecological footprint by selecting eco-friendly accommodations, encouraging waste reduction, and supporting sustainable transportation options where possible. Our walking tours are designed to immerse participants in the local culture, fostering meaningful connections with the communities we visit. We strive to leave a positive impact by engaging in responsible tourism activities, respecting local customs, and contributing to the preservation of natural landscapes. Through our commitment to responsible travel, we aim to create enriching experiences for our guests while actively contributing to the conservation of the destinations we explore.

The Ramble Worldwide Outdoor Trust

Unlike many other tour operators, we take pride in our unique approach. Ramble Worldwide channels its surplus profits back into various outdoor, walking-related, or environmental conservation projects in the UK through our own trust. When you choose us, you contribute to this impactful initiative.

The Ramble Worldwide Outdoor Trust is passionate about making the outdoors more accessible for more people from all communities. We grant funds to many organisations and have recently partnered with Mind Over Mountains, Adaptive Grand Slam, and other groups to create an enduring impact on people’s lives and to support them to enjoy the outdoors. In addition, the Trust makes many small grants to local organisations such as Ramblers Groups, Walkers are Welcome, My kind of Books and recently provided a small grant, via his scouting group, to enable a young man whose family had fallen on hard times to complete his DofE Gold award.

Patron of the Trust is the renowned explorer, Mark Wood. Over 20 years Mark has undertaken expeditions to some of the most remote parts of our planet. Our shared values make for an exciting partnership, and we believe that by standing shoulder to shoulder we can encourage people from all communities to enjoy being active outdoors in whatever way suits them best.

For more comprehensive details, please visit the 'About' section on our website and click on the Charitable Trust link. Your choice to travel with us goes beyond a memorable vacation; it contributes to meaningful projects that have a positive impact on our community and environment.

Staying In Touch

Mobile Phones

Kindly share a mobile phone contact number with us. We'll utilise this solely for crucial communication pertaining to your holiday arrangements.

Ensure your mobile phone remains switched on and easily accessible when en-route to the airport or during transit delays. This way, we can promptly reach you with any last minute updates concerning your travel plans.

In consideration of others, we request that you switch off your mobile phone during walks or try to limit its usage. Additionally, during group meals, please minimise the use of mobile devices. Your co-operation ensures a seamless and enjoyable experience for everyone on the journey.

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