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Dorset Guided Walking

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Duration: 5 nights
Type: Guided walking
Walking Grade: 2 & 3
from £1,029pp

Discover Dorset and the Jurassic Coast on this guided walking holiday. Spanning over 96 miles, this coastline reveals 185 million years of history. Explore the fossil-filled beaches, Caribbean-like coves, and enchanting castles, that have earned this part of Dorset UNESCO World Heritage status. Highlights include Lulworth Cove, the chalk stacks of Old Harry Rocks, and Durdle Door, an impressive limestone arch carved by centuries of erosion. Our carefully planned walks showcase the area’s top sights with daily guided options offering a fantastic way to explore this enchanting stretch of UK coastline.

What you’ll love

  • A choice of two walks each day
  • Exploring UNESCO World Heritage Site – the Jurassic Coast
  • Tackling some of the UK’s finest coastal walks
  • Learning about the natural history that makes this area famous
  • Snapping shots of Lulworth Cove, Durdle Door, & Osmington White Horse
  • Discovering hidden gems, far from the crowds

What’s included

  • Comfortable en-suite rooms in our partner accommodation
  • Cooked or continental breakfast every morning 
  • Daily packed lunches
  • Three-course evening meals, plus tea & coffee  
  • Guided walks with experienced HF Holidays Leaders
  • All transport to and from walks where necessary 

Trip Notes

Easy to download as a PDF, our trip notes provide detailed information for every holiday. Please click below to find the trip notes for your departure date.

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.

Check in at the hotel is available from 3pm. Your leaders will be at reception at 18:30 to meet the group and to give you a quick introduction to the holiday before dinner.  


Option 1 - Corfe Castle

Distance: 7½ miles (11½km)

Ascent: 770 feet (240m) 

Descent: 1,100 feet (340m)

Walking right from our door, we head out to Swyre Head, the highest point on the Isle of Purbeck for excellent views from St Aldhelm's Head in the east to Portland Bill in the west.  We then head inland to Knowle Hill and Corfe Castle Village where there will be plenty of time to explore. Relax in sun outside one of Corfe's cafes, watch for steam trains, or visit the romantic ruins of Corfe Castle, before a short ride on the local bus takes us back to our hotel.

Option 2 - Kingston and Kimmeridge

Distance: 10 miles (16km) 

Ascent: 1,330 feet (410m) 

Setting off on our walk direct from the hotel door, we’re treated to a circular route that takes in Swyre Head – the highest point on the Isle of Purbeckand picturesque Kimmeridge Bay, where a giant pliosaur skull was discovered in 2022. There’s time to take a peek inside the Wild Seas centre, which will reveal what nature to look out for on our walks over the next few days.  


Option 1 - Langton Matravers to Swanage

Distance: 6 miles (10km) 

Ascent: 790 feet (250m) 

Walk from the village of Langton Matravers to the coast at Dancing Ledge, a popular spot for rock climbers. From here we head east along the South West Coast Path, with time to visit the Durlston Castle visitor centre before continuing to Swanage. We’ve time to explore this traditional seaside resort with its beach, pier and steam railway. 

Option 2 - Kingston to Swanage

Distance: 11 miles (18km) 

Ascent: 1,590 feet (490m) 

Departing from the door of the hotel again today, we’ll head down to the coast towards pretty Chapman’s Pool and St. Aldhelm’s Head. From here the route follows the South West Coast Path, passing old quarries and Dancing Ledge to reach Swanage.    


Option 1 - Corfe and Studland

Distance: 6½ miles (10 ½ km) 

Ascent: 940 feet (290m) 

Enjoy a stunning variety of inland and coastal scenery today. Our walk from Corfe Castle to Studland follows the glorious chalk ridge along the spine of the Purbeck peninsula, with the views getting ever more impressive as we near our destination. Panoramic views stretch north over Poole Harbour, and south to the English Channel. 

Option 2 - Corfe, Old Harry Rocks & Studland

Distance: 11 miles (17 ½ km) 

Ascent: 1,260 feet ascent/1,560 feet descent (390m ascent/480m descent) 

Leaving directly from our hotel, we’ll walk over rolling countryside to Corfe with its romantic castle ruins and steam railway. We cross the railway then take a fabulous chalk ridge along the spine of the Purbeck peninsula to Ballard Down and the coast at Old Harry Rocks. On a fine day you’ll see as far as the Needles on the Isle of Wight. 


Option 1 - Osmington to Lulworth

Distance: 7½ miles (12km) 

Ascent: 1,200 feet (370m) 

There’s a trio of highlights today; the pretty smuggler’s cove of Osmington, the iconic Durdle Door limestone arch, and the teardrop-shaped  Cove. The section from Durdle Door to Lulworth Cove is a busy one, but we’ll see why when we get there. Be sure to bring your camera for plenty of photos. 

Option 2 - Overcombe to Lulworth Cove along the Coast Path

Distance: 9 miles (14½ km)

Ascent: 1,770 feet (540m)

Starting from the edge of Weymouth we pass through the smuggler’s haunt of Osmington Mills and follow the fabulous roller coaster coast path all the way to Lulworth Cove. Tick off the geological wonders of Durdle Door and Stair Hole along the way.



Itinerary map for Dorset

Kingston Country Courtyard

The Kingston Country Courtyard is ideally located for exploring Purbeck and its stunning coastline. This converted farmstead features rustic yet comfortable ensuite rooms, all with free Wi-Fi, TV, and tea and coffee facilities. Enjoy outdoor seating in the courtyard and gardens, with views stretching to the coast and Corfe. All rooms open onto the original farm courtyard. The hotel is dog-friendly, so you might meet some four-legged friends in communal areas. Free parking is available for residents.

Please note, some of the bathrooms at the hotel are wetrooms - a wet room is a style of bathroom where there's no separation between dry and wet areas. These make the bathrooms highly accessible.

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Getting to Kingston Country Courtyard

Find out more about this location including travel details and room types.

More Information

Essential information

The UK has a famously unpredictable climate so it's best to be prepared for weather that’s sunny one minute and raining the next.  To make it easier, here’s a list of items you should consider packing.   

Essentials  

  • Suitable footwear such as waterproof walking boots that provide ankle support and good grip  
  • Waterproof and windproof jacket 
  • Comfortable clothing (jeans & waterproof capes are not suitable)  
  • Mid-layer(s) to keep you warm. Fleeces make a good choice
  • Waterproof overtrousers  
  • Gloves and a warm hat  
  • Rucksack with waterproof liner 
  • Flask for hot drinks   
  • Water bottle (at least 1 litre capacity)  
  • Sunscreen  
  • UV sunglasses  

Recommended  

  • Several base layers (long-sleeve or short-sleeve)  
  • Cushioned walking socks to avoid blisters  
  • First aid kit, including plasters and insect repellent 
  • Sit mat   
  • Waterproof pouch for valuables  
  • Rubbish bag (remember to always leave no trace)  
  • Wallet/purse  
  • Camera 

Guest reviews

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Holiday prices

Date (Start - End) Itinerary Double / Twin Room Single Room Notes / Offers Trip Notes Book
2025

14 Sep - 19 Sep 2025

5 nights

Itinerary

Single from

£1,029

Double from

£1,029 pp

from

£1,029 pp

from

£1,029

Trip Notes
Book Now

21 Sep - 26 Sep 2025

5 nights

Itinerary

Single from

£1,274

Double from

£1,029 pp

from

£1,029 pp

from

£1,274

Trip Notes
Book Now

05 Oct - 10 Oct 2025

5 nights

Itinerary

Single from

£1,274

Double from

£1,029 pp

from

£1,029 pp

from

£1,274

Trip Notes
Book Now
Duration:
5 nights
Type:
Guided walking
Walking Grade:
2 & 3

5 nights from £1,029pp

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Carbon Footprint 110Kg of CO₂e

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