Cliffside view of a seaside village with red-roofed houses, lush greenery, and steep cliffs overlooking the ocean under a partly cloudy sky.
Ruins of an old stone church on a grassy landscape with a small pond in the foreground, under a partly cloudy sky.
Scenic view of a coastal town with colorful houses on a hill, a beach, and a sailboat docked at a pier on calm water under a clear blue sky.
Cliffside overlooking the ocean with a wooden signpost in the foreground pointing towards Hawksea and Cleveland.
Scenic view of lush green fields, rolling hills, trees with white blossoms, and a coastal cliff beside the blue ocean under a partly cloudy sky.

Whitby & Robin Hood’s Bay - Yorkshire Coast Walking Weekend

Discover the Yorkshire Coast on a sociable walking weekend exploring Whitby, Robin Hood’s Bay and Ravenscar. From dramatic clifftop paths and historic fishing villages to smugglers’ tales and the remains of a Victorian railway, this three-night break brings together some of the best walking and most fascinating stories along the Yorkshire coastline.

We'll follow beautiful stretches of the Cleveland Way, explore the cobbled streets of Whitby and Robin Hood’s Bay, and discover Ravenscar, the fascinating ‘town that never was’.

You'll stay in a comfortable hotel near the beach in Scarborough, with guided walks, transport to and from the routes and plenty of time to enjoy the company of your fellow walkers. Most people join us on their own, and with a complimentary collection from Scarborough railway station, it's easy to enjoy the weekend without bringing a car.

Holiday at a Glance

Duration
2 nights · 2 walking days

Walking grade
Leisurely Plus

Distance
Approx. 8-10 miles per day

Price
From £325pp

 

Group size
Maximum 8

Accommodation
Hotel

Transport
Car-free · Transport included

Meals
Breakfasts included

 

Check Dates & Book Your Place

Select a date to check availability, room options and prices.

Upcoming departure dates

  • Friday 23 - Sunday 25 April 2027

  • Friday 1 - Sunday 3 October 2027

Deposits – Pay a 20% deposit when booking more than 12 weeks before departure. The remaining balance is due 12 weeks before departure.

 
whalte bones at whitby.jpg

Coastal Walking, Fishing Villages & Yorkshire History

There's much more to the Yorkshire Coast than its wonderful sea views, although you'll certainly enjoy plenty of those!

Our walks take us along the Cleveland Way National Trail, past towering sea cliffs and historic industrial remains, with time to explore some of Yorkshire's best-loved coastal villages.

In Whitby, discover the town's connections to Captain Cook, Bram Stoker's Dracula and the famous abbey overlooking the harbour. In Robin Hood's Bay, wander through narrow streets once associated with smugglers and fishermen.

We'll also explore Ravenscar, where grand Victorian plans for a seaside resort never quite became reality, before following the peaceful Cinder Track along the route of the former Whitby–Scarborough railway.

With friendly company, relaxed evenings and the chance to enjoy traditional Whitby fish and chips, it's a lovely way to spend a few days exploring the Yorkshire Coast.

Trip Highlights

  • Whitby & Robin Hood’s Bay – Explore historic fishing villages, cobbled streets, independent shops and traditional seaside charm.

  • The Cleveland Way – Enjoy two days of coastal walking with sweeping North Sea views, dramatic cliffs and beautiful bays.

  • Ravenscar & the Alum Works – Discover the ‘town that never was’ and the remains of Yorkshire's fascinating industrial past.

  • The Cinder Track – Follow the peaceful former railway line between Robin Hood's Bay and Ravenscar.

  • A sociable small-group break – Friendly guided walks, relaxed evenings and plenty of opportunities to meet new people.

Walkers taking on the Cleveland Way on the Yorkshire Coast

Discover the Yorkshire Coast on Foot

Stretching from salt-washed headlands to sheltered bays, the Yorkshire Coast blends striking coastal scenery with stories that span centuries. Walking here brings together sea cliffs, old railway paths, moorland edges and villages shaped by fishing, trade and folklore.

Along the way you’ll find reminders of shipwrecks, smugglers, early industry and the region’s maritime heritage. Seabirds nest on the cliffs, seasonal wildlife moves through the coves, and the geology reveals layers of Jurassic history. Whether it’s the coastal paths near Whitby or the steep lanes of Robin Hood’s Bay, every section has its own character and rhythm.

Leisurely coastal walking in this area offers a relaxed way to explore, taking in the views, fresh air and constant shift of tides – all with the space to enjoy the journey rather than rush it.

Suggested Itinerary

Here’s what we’ve got planned - of course, we may have to offer alternatives or make amendments if the weather misbehaves or other unexpected situations arise!

  • Your Yorkshire Coast walking weekend begins with check-in at the hotel from 15:00, giving you plenty of time to arrive, unpack and settle in.

    In the evening, you'll meet your Large Outdoors guide and fellow walkers in the hotel bar before enjoying dinner together. It's a relaxed and sociable start to the weekend, with plenty of opportunity to get to know everyone and look forward to the walks ahead.

    We'll be dining at the hotel, making things easy for anyone arriving a little later, as you won't need to head out or find the group elsewhere.

    Travelling by train? We offer a complimentary collection from Scarborough railway station at 18:00, making it easy to join us without a car. Station collection must be booked in advance.

  • Distance: 7–9 miles

    After a hearty cooked breakfast, we head to Whitby before hopping on a local bus to the picturesque fishing village of Robin Hood’s Bay.

    With its maze of narrow cobbled streets, old fishermen’s cottages and fascinating smuggling history, Robin Hood’s Bay is a wonderful place to explore. We'll have time to wander through the village before setting off along one of Yorkshire’s finest stretches of coastline.

    Following the Cleveland Way National Trail, we make our way back towards Whitby, with dramatic sea cliffs, sweeping coastal views and the North Sea stretching out beside us. It's a lovely walk, with plenty of opportunities to stop, take photographs and enjoy the scenery.

    Arriving in Whitby, we'll have time to discover what makes this historic seaside town so special. Famous for its connections to Captain Cook, its fishing heritage and Bram Stoker’s Dracula, Whitby is packed with character. You might fancy climbing the famous 199 Steps to explore the atmospheric ruins of Whitby Abbey, wandering through the independent shops of the old town or simply watching the boats come and go in the harbour.

    And, of course, no visit to Whitby would be complete without fish and chips! We'll finish the day with the chance to enjoy this Yorkshire seaside favourite, with everyone free to choose where and what they'd like to eat.

    Afterwards, your guide will drive everyone back to the hotel.

  • Distance: 7–9 miles*

    After breakfast and checking out of the hotel, we head north to Ravenscar for another lovely day exploring the Yorkshire Coast.

    Perched high above the North Sea, Ravenscar is often called ‘the town that never was’. In the late Victorian era, ambitious plans were drawn up to transform this dramatic clifftop location into a fashionable seaside resort, complete with streets, houses and hotels. The development never really took off, leaving behind a fascinating story and one of the quieter corners of the Yorkshire Coast.

    From Ravenscar, we join the Cleveland Way National Trail, following the spectacular coastal path towards Robin Hood’s Bay. Along the way, we'll discover the remains of the historic Ravenscar Alum Works, where alum was produced for centuries and played an important role in Britain's textile industry.

    With sweeping views across the North Sea, rugged cliffs and the picturesque coastline stretching ahead, this is a wonderful stretch of walking and a lovely way to round off our weekend.

    Reaching Robin Hood’s Bay, we'll stop for a well-earned coffee, perhaps a slice of cake and a comfort break before beginning our return journey. Having explored the village the previous day, today is more about enjoying the walk and taking in the scenery.

    For our return to Ravenscar, we swap the clifftop paths for the Cinder Track, the former railway line that once connected Whitby and Scarborough. This peaceful, gently graded route takes us through the countryside, offering a completely different perspective on the coast and its railway heritage.

    Back in Ravenscar, if time allows, we may stop at the local tearoom for some light refreshments before heading back to Scarborough.

    We'll aim to drop everyone back at the hotel to collect their cars, or at Scarborough railway station for onward travel, by 16:00.

    A lovely mix of coastal scenery, local history and sociable walking to finish our Yorkshire Coast weekend.

Robin Hood's Bay

Robin Hood’s Bay – Stories, Smugglers and Coastal Folklore

Robin Hood’s Bay has long captured people’s imagination, though there’s no firm link to the famous outlaw himself. The name may come from old coastal ballads or earlier Norse traditions, but its real history is just as compelling.

During the 18th century, the village became one of the busiest smuggling centres on the Yorkshire Coast. Rum, tea, brandy and tobacco were secretly moved through a warren of interconnected cottages, with stories of goods passing from attic to cellar without ever touching the street. Today, the steep lanes, sea views and hidden alleys still carry that sense of mystery, with local legends and maritime history woven into almost every corner.

Essential Information

  • Meeting Time: Check-in from 15:00.

    The Large Outdoors host will meet you in the bar from 18:00.

    Meeting Location:
    Premier Inn Scarborough (North Bay)
    26 Burniston Rd,
    Scarborough
    YO12 6PH

    Free Station Collection:
    We will be offering a free collection from Scarborough Train Station at 18:00. This is free but must be booked in advance, either during your booking process of by contacting the office in advance.

    Parking:
    On-site parking is available at the hotel. The car park is owned by Scarborough Borough Council and is £6 between the hours of 9am to 6pm. Outside of these hours the car park is free of charge. This can be paid for via the pay and display machine in the car park which accepts card and cash or via the Ringgo app using code 44646.

    Finish Time:
    We aim to finish on the final day between 1pm and 3pm - the exact finish time may depend on the planned/chosen activity, group dynamic, weather conditions, whether the group chooses to grab a coffee or lunch together during/after, etc. If you’ve travelled via public transport, please ensure you book onward travel accordingly (i.e. an open return ticket), to allow for flexibility.

  • We'll be staying at the Premier Inn Scarborough (North Bay) hotel, located on Burniston Road in Scarborough's North Bay. The hotel offers comfortable rooms and is conveniently situated less than a mile from Scarborough Beach and Scarborough Castle.

    Accommodation Address:
    Premier Inn Scarborough (North Bay)
    26 Burniston Rd,
    Scarborough
    YO12 6PH

    Room Types:
    Single Rooms (en-suite bathroom) are for one participant.
    Double Rooms (en-suite bathroom) sleep up to two participants booking together, in a Double bed.
    Twin Rooms (en-suite bathroom) for for two people sharing and will have two single beds.
    Shared Male / Female Rooms (en-suite bathroom) ideal for those happy to share with another participant.

  • Included:

    • 2 nights’ bed & breakfast accommodation.

    • A hearty cooked breakfast each morning, prepared by the accommodation.

    • A Large Outdoors host/guide to welcome you, deal with the logistics for your experience.

    • Guided walks on three days (Days 2 & 3).

    Not included:

    • Travel to and from the meeting location or train station collection.

    • Evening Dinners - we’ll book a table at a local pub to enjoy dinner as a group and you can purchase whatever you fancy from the menu available.

    • Packed Lunches - for these we will stop at a local bakery and you can purchase what you wish for lunch.

    • Any extra (i.e. not mentioned above in ‘Included’) excursions or activities that you may partake in which incur a cost.

    • Alcoholic drinks - please feel free to bring something with you to enjoy at the accommodation. There are also a couple of pubs in the village for a post-walk pint or two!

    • Any food, drinks or goods you choose to purchase at any shops, restaurant, pubs or cafés visited.

    • Travel/activity insurance - we recommend having insurance to cover, at a minimum: cancellation and curtailment; medical and emergency expenses (including repatriation); personal accident; injury and death.

  • Please see our Residential (Walking) Kit List.

    The compulsory items are selected for your safety, which is of paramount importance to us at Large Outdoors. Each participant should have the items listed.

    • What level of fitness is needed?
      This trip is rated ‘Leisurely’. The longest walk will be around 8 miles at a sociable pace.

    • Can I attend on my own?
      Absolutely! In fact, the majority of our attendees are solo travellers.

    • When should I arrive?
      You are welcome to arrive from 15:00 onwards on Friday evening. Dinner will be served at the accommodation at around 19:30. If you intend to arrive after 22:00, please let us know.

    • I’d prefer vegetarian or vegan meals - can this be arranged?
      Yes, absolutely! We will always supply a vegetarian or vegan meal, but please note this must be requested well ahead of the trip - the remote location of our accommodation means we can’t pop out to buy additional ingredients. Complete the dietary section during the booking process and if your dietary needs change ahead of the trip please email the office and we’ll update your booking.

    • I’d prefer gluten-free meals - can this be arranged?
      We will provide meals using gluten-free ingredients, but due to the shared nature of the kitchen we cannot provide strictly gluten-free meals. Please let us know you’d like gluten-free ingredients ahead of time by completing the dietary section during the booking process.

    • I am allergic to a specific ingredient - can you provide meals for me?
      Due to the shared nature of the kitchen we are unable to provide meals suitable for those suffering from many allergies. Please contact the office before booking to discuss your requirements.

    • What transport is provided during this trip?
      We do not provide transportation during this trip.

    • Can I bring my dog?
      Dogs are not allowed on this trip, except for registered assistance dogs.

Check Dates & Book Your Place

Select a date to check availability, room options and prices.

Upcoming departure dates

  • Friday 23 - Sunday 25 April 2027

  • Friday 1 - Sunday 3 October 2027

Deposits – Pay a 20% deposit when booking more than 12 weeks before departure. The remaining balance is due 12 weeks before departure.

 

Questions Before You Book?

Not sure whether this walking holiday is right for you? We're always happy to help with questions about the walks, accommodation or joining us on your own.

Email hello@largeoutdoors.com or get in touch through WhatsApp.