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Walk the South Downs Way

A walk along the chalk downs of Hampshire and Sussex, from Winchester to Eastbourne.

3 to 11 nights
18-100 miles
Moderate to Demanding / Strenuous

Contours Self-Guided Walking Holidays

Contours provide everything you need to discover the South Downs Way at your own pace.

The South Downs Way

  • Walk the length of the chalk downs of Hampshire and Sussex, enjoying a refreshing mix of both inland and coastal landscapes.

  • Discover a range of historic landmarks, including Norman and Saxon churches, old thatched villages and the spectacular cathedral city of Winchester.

  • Complete the full 100-mile trek in Eastbourne and take in breath-taking views from Birling Gap, the Seven Sisters cliffs and Beachy Head.

Standard
Interactive
© Contours Walking Holidays South Downs Way map
Winchester to Eastbourne
100 miles (160 km)
2nd January to 24th December

Available tours

CodeTourDurationDifficultyPrice per person
SDW1 From Winchester to Eastbourne 7 nights, 6 days walking Demanding / Strenuous£750
SDW2 From Winchester to Eastbourne 8 nights, 7 days walking Moderate / Demanding£860
SDW3 From Winchester to Eastbourne 9 nights, 8 days walking Moderate / Demanding£965
SDW4 From Winchester to Eastbourne 10 nights, 9 days walking Moderate£1070
SDW5 From Winchester to Eastbourne 11 nights, 10 days walking Moderate£1180

Select a tour

About Contours Holidays

Contours Walking Holidays organise self-guided walking tours in the UK and Ireland. We arrange everything so that you can walk your chosen route at your own pace. Our holidays are flexible, customisable and suit walkers of all ages and abilities. We also cater for solo travellers, gruops, families and walkers with dogs, thanks to our extensive selection of itineraries.

What's included

Shorter Walks

Not keen on tackling the full South Downs Way? Then look to our alternative routes on this trail below, or browse the rest of our website. We have a range of over one hundred unique trails, each with their own special charm, so you're sure to find a self-guided walking holiday that suits you.

Routes on this trail

South Downs Way - West Section
4 to 6 nights
48 miles
Moderate+
From £430 per person
A self-guided walking holiday from Winchester to Amberley along the chalk downs escarpment.Find Out More
South Downs Way - East Section
5 to 6 nights
51 miles
Moderate+
From £535 per person
A walking holiday from Amberley to Eastbourne along the chalk South Downs escarpment to the coastal clifftops.Find Out More
South Downs Way Short Break - Circular
3 nights
18 miles
Moderate
Dog friendly
From £330 per person
A circular walking holiday from Alfriston via the Seven Sisters Cliffs, Beachy Head, and Eastbourne.Find Out More
South Downs Way Short Break - East Section
3 nights
23 miles
Moderate
From £330 per person
A taster break along the most southerly stretch of the trail from Kingston-near-Lewes to Eastbourne.Find Out More
South Downs Way
7 to 11 nights
100 miles
Moderate+
From £750 per person
A walking holiday from Winchester to Eastbourne along the chalk downs of Hampshire and Sussex.Find Out More
South Downs Way Short Break - Central Section
3 nights
23 miles
Moderate
From £330 per person
A short walking holiday from Buriton to Amberley on a central snippet of the South Downs Way.Find Out More

Customer reviews from the South Downs Way

“I thought the accommodations and the food served was wonderful.”
Mr King, USA
“Easy walking in pleasant countryside.”
Mr Syme, UK
“Overall it is a good walking holiday. The walking is path is everywhere very well indicated, and the paths are well maintained. The accommodations are also of good level.”
Ms Creusot, Netherlands
“Fabulous holiday despite the weather - many thanks.”
Dr Langdon, UK
“We have had many holidays around the world traveling to 6 continents staying in 5 star hotels and resorts and both my wife and myself enjoyed our walking holiday more than any ( despite not perfect weather). Wonderful countryside and everything went to plan. Have already recommended to a golfing friend. Taxis arrived on time baggage was always waiting for us and a varied selection of B&B , Guest houses and pubs.”
Mr Styles, UK
“It’s a beautiful walk and not many people get to walk parts of it in snow banks.”
Mr Miller, USA
“Lovely walk and great accommodation.”
Mr Callan, UK
“We enjoyed our holiday very much, an excellent walk and really good accommodation at every stage.”
Mr Carrier, UK
“This was our 5th Contours holiday and was of the excellent standard we have come to expect from Contours.”
Mr McDonough, UK