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£720
SDW2 From Winchester to Eastbourne 8 nights, 7 days walking Moderate / Demanding£820
SDW3 From Winchester to Eastbourne 9 nights, 8 days walking Moderate / Demanding£920
SDW4 From Winchester to Eastbourne 10 nights, 9 days walking Moderate£1025
SDW5 From Winchester to Eastbourne 11 nights, 10 days walking Moderate£1125

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 walkers, 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

5 to 6 nights
51 miles
Moderate+
From £515 per person
A walking holiday from Amberley to Eastbourne along the chalk South Downs escarpment to the coastal clifftops.Find Out More
3 nights
18 miles
Moderate
Dog friendly
From £320 per person
A circular walking holiday from Alfriston via the Seven Sisters Cliffs, Beachy Head, and Eastbourne.Find Out More
3 nights
23 miles
Moderate
From £320 per person
A taster break along the most southerly stretch of the trail from Kingston-near-Lewes to Eastbourne.Find Out More
7 to 11 nights
100 miles
Moderate+
From £720 per person
A walking holiday from Winchester to Eastbourne along the chalk downs of Hampshire and Sussex.Find Out More
3 nights
23 miles
Moderate
From £320 per person
A short walking holiday from Buriton to Amberley on a central snippet of the South Downs Way.Find Out More
4 to 6 nights
48 miles
Moderate+
From £415 per person
A self-guided walking holiday from Winchester to Amberley along the chalk downs escarpment.Find Out More

Customer reviews from the South Downs Way

“A well organised and wonderful trip in stunning countryside, was surprisingly empty of people save the occasional dog walker and mountain biker at the weekend.”
Dr Watson, UK
“Contours really delivered a great service.”
Mr Mahon, UK
“I do like the way that whoever answers the phone at Contours seems to know all the details and is able to deal with matters immediately.”
Mr Simmons, UK
“This was our 5th Contours holiday and was of the excellent standard we have come to expect from Contours.”
Mr McDonough, UK
“A wonderful experience. The South Downs is a beautiful is a beautiful area and a wonderful place to walk.”
Dr Reader, Canada
“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
“All stages of planning and accommodations arrangements went flawlessly thanks to your great organisation.”
Ms Reynolds, USA
“Fabulous holiday despite the weather - many thanks.”
Dr Langdon, UK
“Overall a great success and we enjoyed it…”
Mrs Lewis, UK