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 £425 per person

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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.

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

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 £970 per person

South Downs Way

Book your walking holiday along the South Downs Way and explore 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, where you'll enjoy magnificent coastal panoramas from atop the rolling clifftops of the famous Seven Sisters.

Available tours

Code Tour Duration Difficulty Price per person
SDW1 From Winchester to Eastbourne 7 nights, 6 days walking Demanding / Strenuous £970
SDW2 From Winchester to Eastbourne 8 nights, 7 days walking Moderate / Demanding £1105
SDW3 From Winchester to Eastbourne 9 nights, 8 days walking Moderate / Demanding £1240
SDW4 From Winchester to Eastbourne 10 nights, 9 days walking Moderate £1375
SDW5 From Winchester to Eastbourne 11 nights, 10 days walking Moderate £1475

Short breaks

Code Tour Duration Difficulty Price per person
SDWSBE From Kingston-near-Lewes(T) to Eastbourne 3 nights, 2 days walking Moderate £425

South Downs Way 7 nights, 6 days walking

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

Travel to Winchester where your first night's accommodation will be booked

Day 1

Winchester to East Meon. 17 miles (27km) / 1772 ft (540 m) ascent

Day 2

East Meon to Cocking. 18.5 miles (29.5km) / 2333 ft (711 m) ascent

Day 3

Cocking to Washington(L). 17.5 miles (28km) / 2073 ft (632 m) ascent

Day 4

Washington(L) to Pyecombe(L). 15 miles (24km) / 1942 ft (592 m) ascent

Day 5

Pyecombe(L) to Alfriston. 21.5 miles (34.5km) / 2365 ft (721 m) ascent

Day 6

Alfriston to Eastbourne. 12 miles (19.5km) / 1742 ft (531 m) ascent

Finish

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 travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

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 on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£70.00 per person / per night
Single Supplement
£55.00 per person / per night


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

Extra night (Standard)
£65.00 per person / per night
Extra night (Pyecombe(L))
£80.00 per person / per night
Standard
Interactive
© Contours Walking Holidays South Downs Way map
Winchester to Eastbourne
102 miles (163 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.

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)
£65.00 per person / per night
Extra night (Pyecombe(L))
£80.00 per person / per night

Tour Facts

Total distance: 101.5 miles (162.5 km)
Duration: 7 nights, 6 days walking
Minimum daily distance: 12 miles (19.5 km)
Maximum daily distance: 21.5 miles (34.5 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 cities 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 (and occasionally Paddington) stations 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.
"Dew Pond near Clayton" by Paul Day (2023) "Dew Pond near Clayton" by Paul Day (2023)
"The George Inn, Alfriston" by Paul Day (2023) "The George Inn, Alfriston" by Paul Day (2023)
"Kingston Lewes" by Sue Daber (2023) "Kingston Lewes" by Sue Daber (2023)
"Winchester Cathedral" by Sue Daber (2023) "Winchester Cathedral" by Sue Daber (2023)
"Kissing Gate above Amberley" by Lesley Kenworthy (2023) "Kissing Gate above Amberley" by Lesley Kenworthy (2023)
"Eastbourne Pier" by Lesley Kenworthy (2023) "Eastbourne Pier" by Lesley Kenworthy (2023)
"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

“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
“We always enjoy walking holidays with Contours!”
Mrs Needham, 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
“Thank you for organising our walk along the SDW. We thoroughly enjoyed it even if we did moan a bit on some of the hills. The only downside was its accessibility to cyclists. Too many going far too fast. Next time I'll choose a route with lots of stiles and very rough ground!”
Ms Willey, UK
“Lovely walk and great accommodation.”
Mr Callan, UK
“Well organised and worthwhile long distance walk. Always good to deal with Contours. Would certainly recommend you.”
Mr Johnson, UK
“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
“I really enjoyed the walk in spite of the uncomfortably hot weather. All of our accommodations were good and the luggage services excellent. Thanks to your staff in the office, everyone was very helpful and ready to sort things out when we made some changes on dates and accommodations.”
Mrs Parker, UK
“Standard of all B&B's perfectly acceptable. You never let us down!”
Mr Evans, UK
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