South Downs Way

A walking holiday from Winchester to Eastbourne along the chalk downs of Hampshire and Sussex.

7 to 11 nights
100 miles
Moderate to Demanding / Strenuous

From £720 per person

Discover the available tours

About this route

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.

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

Holiday highlights

Exploring the cathedral city of Winchester, once the capital of Saxon England, and Alfriston’s parish church, the “Cathedral of the Downs”.

Visiting the downland viewpoints of Beacon, Butser and Bignor Hills, Ditchling Beacon and Firle Beacon.

Arriving in Eastbourne to breath-taking views from Birling Gap, Seven Sisters Cliffs, and Beachy Head.

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

South Downs Way 7 nights, 6 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather

Travel to Winchester where your first night's accommodation has been booked

Day 1

Winchester to East Meon. 17 miles (27km)

Day 2

East Meon to Cocking. 19 miles (30.5km)

Day 3

Cocking to Washington(L). 18 miles (29km)

Day 4

Washington(L) to Pyecombe. 13.5 miles (21.5km)

Day 5

Pyecombe to Alfriston. 22 miles (35km)

Day 6

Alfriston to Eastbourne. 12 miles (19.5km)


Depart from Eastbourne after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to walk more than a mile from the trail to your accommodation; should your accommodation be further than this, transfers will be provided as standard.

Below are the additional costs that may apply depending on your requirements. Dog friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are walking on your own, or are part of a group but require a room of your own, then the Solo Walker or Single Supplements apply respectively:

A note about transfers
Solo Walker Supplement
£45.00 per person / per night
Single Supplement
£35.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£60.00 per person / per night

What's included?

  • 7 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

If you would like to extend your holiday by taking an extra night, there are a number of locations for you to consider.

An extra night in Winchester could be an excellent start to your holiday. A walk up St Giles Hill offers spectacular views over the city, while a visit to Winchester Cathedral, one of Europe's largest cathedrals, offers an insight to a whole range of treasures, including Jane Austen's tomb and the Winchester Bible. For fans of Arthurian legend, the Great Hall of Winchester Castle features the round table, while a stroll through the city reveals Georgian buildings, Saxon streets and the gothic architecture of the Victorian Guildhall.

If you would like to spend some more time exploring at the end of your walk, consider Eastbourne for an extra night. With spectacular views from Beachy Head and a host of historic locations such as Redoubt Fortress as well as shops, parks, gardens, restaurants, museums and galleries, there is plenty to serve as reward after completing your walk.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£60.00 per person / per night

Tour Facts

Total distance: 100 miles (160 km)
Duration: 7 nights, 6 days walking
Minimum daily distance: 12 miles (19.5 km)
Maximum daily distance: 22 miles (35 km)
Code: SDW1 Grade: Demanding / Strenuous
Season: 2nd January - 24th December
Start of holiday: Winchester
End of holiday: Eastbourne

Route Profile

South Downs Way Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Southampton, Bournemouth, London Gatwick and London Heathrow.

By Rail - There is a rail station at the start of the trail (Winchester) and also at the end of the trail (Eastbourne).

By Bus - Various bus services run to Winchester and from Eastbourne.

From London - Trains run from London Waterloo station to Winchester.

Return To The Start - The easiest way to return to the start of the trail, is to take the train from Eastbourne to Winchester.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.

Routes on this trail

4 to 6 nights
48 miles
From £415 per person
A self-guided walking holiday from Winchester to Amberley along the chalk downs escarpment.Find Out More
5 to 6 nights
51 miles
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
23 miles
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
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
From £320 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

“It’s a beautiful walk and not many people get to walk parts of it in snow banks.”
Mr Miller, USA
“Standard of all B&B's perfectly acceptable. You never let us down!”
Mr Evans, UK
“Contours Holidays do not disappoint. Well-organised holiday with three people used to walking together.”
Mr McDonough, UK
“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
“Overall a great success and we enjoyed it…”
Mrs Lewis, UK
“Many thanks. We are already planning our next walk for October 2019. It goes without saying that we will be looking to make use of your services again.”
Mr King, 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
“Wake, breakfast, walk, wash, dinner, sleep, repeat--what's not to like? Particularly as the weather was almost universally good and the downs full of flowers, birds and butterflies!”
Ms Myerscough, Australia
“We enjoyed our holiday very much, an excellent walk and really good accommodation at every stage.”
Mr Carrier, UK
"Enjoying a Rest" by Marianne Engelshove (2018)
"Approaching the Coast" by Marianne Engleshove (2018)
"Approaching Eastbourne" by Marianne Engleshove (2018)
"Walking towards the Coast" by Marianne Engleshove (2018)
"Arriving at the Coast" by Marianne Engleshove (2018)
"Meeting with the Wildlife" by Marianne Engleshove (2018)
"South Harting" by Steven McDonough (2017)
"Winchester Almshouses" by Steven McDonough (2017)
"Horse near Pyecombe" by Sam Mitchell (2017)
"Along Juggs Way" by Sam Mitchell (2017)
"Dew Pond" by Sam Mitchell (2017)
"Beachy Head" by Sam Mitchell (2017)
"Sheep Field near Kingston" by Sam Mitchell (2017)

Select a tour