South Downs Way

South Downs Way

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

3 to 11 nights
22-102 miles
Moderate to Demanding / Strenuous

From £415 per person

Find your holiday

About the trail

Walk the length of the chalk downs of Hampshire and Sussex on the South Downs Way, which dips into beautiful river valleys to visit Norman and Saxon churches, deserted medieval villages, and historic thatched villages bursting with flowers.

This spectacular National Trail boasts a wealth of old beacon viewpoints overlooking patchwork fields and woodland. Those inland vistas are matched only by the breath-taking views from chalk clifftop trails out over the English Channel at the adventure’s end. The South Downs Way is a stunning walking holiday through iconic English terrain.

The South Downs Way On Film:

We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.

Choose your route

  • South Downs Way
  • South Downs Way - West Section
  • South Downs Way - East Section
  • South Downs Way Short Break - East Section
  • This route includes dog friendly tour options South Downs Way Short Break - Circular
  • South Downs Way Short Break - Central Section

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

Trail running tours available

We also organise trail running holidays along this route. Find out more.

About this route

7 to 11 nights
102 miles
Moderate to Demanding / Strenuous
2nd January to 24th December

From £925 per person

South Downs Way

This South Downs Way holiday option explores all 100 miles of this spectacular National Trail, setting off from Winchester and scrambling eastwards towards Eastbourne on the coast.

The walk traverses the fabulous chalk downs and offers far-reaching views along its length, however the best scenery arguably comes at the end of your journey, with magnificent coastal panoramas from the rolling clifftops of the famous Seven Sisters.

Walking the South Downs Way with Contours Holidays

Outdoor Journalist Damian Hall takes a walk from Winchester to Eastbourne, crossing the chalk downs of Hampshire and Sussex to the white cliffs at the edge of the English Channel.
Watch Now

Available tours

Code Tour Duration Difficulty Price per person
SDW1 From Winchester to Eastbourne 7 nights, 6 days walking Demanding / Strenuous £925
SDW2 From Winchester to Eastbourne 8 nights, 7 days walking Moderate / Demanding £1055
SDW3 From Winchester to Eastbourne 9 nights, 8 days walking Moderate / Demanding £1180
SDW4 From Winchester to Eastbourne 10 nights, 9 days walking Moderate £1310
SDW5 From Winchester to Eastbourne 11 nights, 10 days walking Moderate £1440

Short breaks

Code Tour Duration Difficulty Price per person
SDWSBE From Kingston-near-Lewes(T) to Eastbourne 3 nights, 2 days walking Moderate £415
"Path down to Kingston near Lewes" by Jay Mirro (2022) "Path down to Kingston near Lewes" by Jay Mirro (2022)
"Landscape near Bramber" by Jay Mirro (2022) "Landscape near Bramber" by Jay Mirro (2022)
"Wide Shot of the South Downs Way" by Jay Mirro (2022) "Wide Shot of the South Downs Way" by Jay Mirro (2022)
"Flowers at Kingston near Lewes" by Jay Mirro (2022) "Flowers at Kingston near Lewes" by Jay Mirro (2022)
"Bridleway along the South Downs Way" by Jay Mirro (2022) "Bridleway along the South Downs Way" by Jay Mirro (2022)
"Well Earned Steak and Ale Pie at Eastbourne" by Jay Mirro (2022) "Well Earned Steak and Ale Pie at Eastbourne" by Jay Mirro (2022)
"Chanctonbury Ring" by Ella Waddingham (2021) "Chanctonbury Ring" by Ella Waddingham (2021)
"Enjoying a Rest" by Marianne Engelshove (2018) "Enjoying a Rest" by Marianne Engelshove (2018)
"Approaching the Coast" by Marianne Engleshove (2018) "Approaching the Coast" by Marianne Engleshove (2018)
"Approaching Eastbourne" by Marianne Engleshove (2018) "Approaching Eastbourne" by Marianne Engleshove (2018)
"Walking towards the Coast" by Marianne Engleshove (2018) "Walking towards the Coast" by Marianne Engleshove (2018)
"Arriving at the Coast" by Marianne Engleshove (2018) "Arriving at the Coast" by Marianne Engleshove (2018)
"Meeting with the Wildlife" by Marianne Engleshove (2018) "Meeting with the Wildlife" by Marianne Engleshove (2018)
"South Harting" by Steven McDonough (2017) "South Harting" by Steven McDonough (2017)
"Winchester Almshouses" by Steven McDonough (2017) "Winchester Almshouses" by Steven McDonough (2017)
"Horse near Pyecombe" by Sam Mitchell (2017) "Horse near Pyecombe" by Sam Mitchell (2017)
"Along Juggs Way" by Sam Mitchell (2017) "Along Juggs Way" by Sam Mitchell (2017)
"Dew Pond" by Sam Mitchell (2017) "Dew Pond" by Sam Mitchell (2017)
"Beachy Head" by Sam Mitchell (2017) "Beachy Head" by Sam Mitchell (2017)
"Sheep Field near Kingston" by Sam Mitchell (2017) "Sheep Field near Kingston" by Sam Mitchell (2017)

Customer reviews from the South Downs Way

“We always enjoy walking holidays with Contours!”
Mrs Needham, UK
“Good”
Mr Kerslake, UK
“A wonderful experience. The South Downs is a beautiful is a beautiful area and a wonderful place to walk.”
Dr Reader, Canada
“Well organised and worthwhile long distance walk. Always good to deal with Contours. Would certainly recommend you.”
Mr Johnson, UK
“The walking was very enjoyable, particularly the latter section, plus the excellent weather.”
Mr Summers, UK
“The walk was full of sweeping views. This was amazing! Can’t wait to book with you again!”
Mr Mirro, USA
“We had a lovely time doing the walk (apart from nursing blisters!) and arrangements went smoothly, so many thanks!”
Ms Barnes, Australia
“We loved it. Beautiful paths, well signposted. Lovely villages and interesting things to see. Sometimes a bit busy but so clean. No litter. Well done Brits!”
Mrs Baines, Netherlands
“It was delightful and very restorative. I rave about you to every cab driver and colleague that will listen. The views, particularly on the downs between Cocking and Alfriston, were spectacular. I love waking up each morning with nothing on my agenda except walking.”
Ms Turnbull, USA
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