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£730
SDW2 From Winchester to Eastbourne 8 nights, 7 days walking Moderate / Demanding£835
SDW3 From Winchester to Eastbourne 9 nights, 8 days walking Moderate / Demanding£940
SDW4 From Winchester to Eastbourne 10 nights, 9 days walking Moderate£1040
SDW5 From Winchester to Eastbourne 11 nights, 10 days walking Moderate£1145

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

5 to 6 nights
51 miles
Moderate+
From £520 per person
A walking holiday from Amberley to Eastbourne along the chalk South Downs escarpment to the coastal clifftops.Find Out More
7 to 11 nights
100 miles
Moderate+
From £730 per person
A walking holiday from Winchester to Eastbourne along the chalk downs of Hampshire and Sussex.Find Out More
4 to 6 nights
48 miles
Moderate+
From £420 per person
A self-guided walking holiday from Winchester to Amberley along the chalk downs escarpment.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
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
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

Customer reviews from the South Downs Way

“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
“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
“Good/excellent accommodation throughout.”
Mr Lea, UK
“Fabulous holiday despite the weather - many thanks.”
Dr Langdon, UK
“It was great, good time and good weather made it worthwhile.”
Mr Wheelock, UK
“We had a super holiday, this walk was fantastic and the weather superb. Thoroughly enjoyable. Contours did a great job in selecting the accommodation and clear and precise admin throughout the holiday booking process. Thanks.”
Mr Ventress, UK
“Reliable luggage transfer and comfortable B&Bs with generous and helpful hosts. Strenuous enough without being painful (speaking as one in my 70's). Breakfasts delicious! Such a wonderful way to experience the countryside (and towns as well). Train and bus options close enough in case weather is really nasty. Thank you all again for organising accommodation, luggage, dates, places and interesting notes on the landscape and area, and for helping me achieve at least one item on my Bucket List!”
Ms Deutscher, Australia
“So lucky with the weather. Views were stunning. Great trail. We have done a lot of trails and always used Contours.”
Mrs Johnson, UK
“We had a lovely time doing the walk (apart from nursing blisters!) and arrangements went smoothly, so many thanks!”
Ms Barnes, Australia