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The South Downs Way
Walking Holiday in Southern England
from Winchester to Eastbourne
in 11 days
10 nights and 9 days walking
Day by Day Itinerary
This 100 mile walking holiday is along the South Downs Way from Winchester to Eastbourne.
This is one of our Southern England Walking Holidays, and also one of our National Trail Walking Holidays.
South Downs Way
Walking Holiday in Southern England
from Winchester to Eastbourne and The English Channel
via Amberley, Steyning and Alfriston
The South Downs Way walking holiday is 100 miles long and is on one of UK’s National Walking Trails. The South Downs Way walking holiday begins at Winchester and follows the South Downs to Eastbourne through on of the UK’s newest National Parks. The South Downs Way walking holiday is clearly way-marked to provide reassurance on your walking holiday in Southern England.
This is a popular walking tour, so we have carefully selected comfortable accommodation to ensure you are well rested each night after a busy day hiking and sightseeing.
The South Downs Way walking holiday connects with:
- Clarendon Way at Winchester
- Pilgrims Way at Winchester
Our self-guided walking holidays are designed with your comfort and enjoyment in mind and can be tailor-made to your own personal requirements.
The routes are clearly way-marked to provide reassurance on your hiking vacation.
We use a selection of guest houses, inns or small hotels with en-suite or private bathroom to ensure you are well rested each night after a busy day hiking and sightseeing. Rest assured that all our accommodation walking holiday providers are hand-picked and offer you that famous British hospitality.
Special diets can be catered for, including vegetarian, vegan, and gluten free.
We organize the luggage transfer so your bags are at your next accommodation when you arrive. We try to get your bags delivered by 4pm, but this may be delayed due to road conditions.
Let’s Go Walking has developed one of the largest selection of walking holidays.
Our offices are staffed 9am to 9pm during our walking season (March to September) to ensure your walking holiday runs without a hitch.
All our walking holidays are self-guided and you must be a confident map reader and able to navigate from a compass bearing. The weather in the UK and Ireland can change quickly effecting visibility and underfoot conditions. It is important to carry a selection of clothing with you on your hike each day to cope with changing weather conditions. If you are not confident of completing any days walk, do not set out.
This walking holiday in the UK operates March to September and in either direction.
The daily distances are only a suggestion. If you would like to walk longer or shorter distances, we can arrange that too.
Our stated distances include mileage to the accommodation or pickup point and so may not agree with the guide book mileages.
Rest days can be taken in any location.
Why not combine this walk with a hiking tour in another part of the UK or Ireland. Our staff will be happy to advise on necessary transfers.
Online booking available.
A deposit of £85 per person is required to secure the booking, with the balance due 6 weeks before departure.
Optional extra days and accommodation upgrades can be added during the booking process online.
Please wait for the confirmation of your holiday before making final travel plans just in case your holiday is not available for your requested date.
South Downs Way Walking Holiday
Winchester to Eastbourne
Suggested Tour Duration:
10 nights, 9 days walking
Total Distance:
100 miles/160 kms
Min/max daily distance:
7/13 miles
Average Daily distance:
11 miles
Grading:
Easy/Moderate
Features:
Winchester Cathedral
South Downs
Devil’s Dyke
Ditchling Beacon
Seven Sisters
Beachy Head
This route connects with:
Clarendon Way
Pilgrims Way
South Downs Way Walking Holiday
in Southern England
from Winchester to Eastbourne on The English Channel
10 nights and 9 days walking
Day by Day Itinerary
Day 1: Arrive at Winchester
To start your South Downs walking holiday you make your own way to Winchester. We can assist with coach or train transfers if necessary. Car parking is available for the duration of your South Downs Way self-guided hiking vacation. This historic city has much to explore, including the fine Cathedral, the Great Hall and Queen Eleanor’s Garden, The Hospital of St Cross, Winchester College, Winchester City Mill, The Gurkha Museum, and The Military Museums. In fact, so much, why not take an extra day. The South Downs Way connects with the Pilgrims Way and Clarendon Way in Winchester.
Optional Day in Winchester
Take an extra day to explore the interesting city of Winchester.
Day 2: Winchester to Exton 12 miles
The hiking trail heads out of Winchester and soon enters the rolling Hampshire countryside. The South Downs Way passes through the village of Chilcomb with a traditional village green and fine thatched cottages. The hiking trail soon reaches Beacon Hill, a National Nature Reserve offering fine views towards Old Winchester and the Meon Valley.
Day 3: Exton to Clanfield 8 miles
Walking on from Exton the South Downs Way passes one of the finest Iron Age hill forts in southern England and offers superb views; on a clear day the Isle of Wight can be seen. The hiking trail soon reaches the highest point on The South Downs Way, the National Nature Reserve at Butser Hill, an area of chalk grassland. Accommodation is limited so it may be necessary to walk a little off route to Petersfield for your overnight stay.
Day 4: Clanfield to Cocking 15 miles
Hiking on through the Queen Elizabeth Country Park the South Downs Way follows the top of the South Downs escarpment. At Harting Down the hiking trail enters a landscape where there are fewer trees offering fine views of the surrounding area, then the hiking trail descends via Beacon Hill and the Monkton Estate to Cocking Down. After reaching Warren Bottom it’s a short distance to the village of Cocking which is only just off the trail.
Day 5: Cocking to Amberley 12 miles
Walking on from Cocking the South Downs Way soon follows a chalk lane back to the top of the South Downs escarpment. The hiking trail passes through the two nature reserves of Heyshott and Graffham Downs. Before reaching Bignor Hill the route crosses Stanes Street, an old Roman road dating back to 500AD. Before reaching the charming village of Amberley the hiking trail enters the Arun Valley.
Day 6: Amberley to Steyning/Bramber 13 miles
Today’s hike starts with a fairly easy walk along the top of the downs with fine views over the swampy landscape of Amberley Wild. The trail then leads to the top of Chanctonbury Hill and its iconic ring of beech trees. The views are far reaching to the English Channel. Today’s walk end at the downland villages of Steyning or Bramber with its beautiful old buildings.
Day 7: Steyning/Bramber to Pyecombe 7 miles
You hike along the level escarpment of the Downs to Devil’s Dyke, with great views in all directions. A short walk takes you to Pyecombe for your overnight stop.
Day 8: Pyecombe to Lewes 10.5 miles
After Pyecombe, you walk past the intriguing Jack and Jill windmills to Ditchling Beacon, then continue along the edge of the escarpment to Lewes.
Optional Day in Lewes:
Take an extra day to explore the interesting town of Lewes with its fine castle and interesting selection of shops and resturants
Day 9: Lewes to Alfriston 12 miles
After crossing the River Ouse you hike back onto high ground and continue along the crest of the escarpment, with the high point being Firle Beacon. Then the path drops steadily down the Alfriston, one of the prettiest villages on the South Downs Way, with its higgledy-piggledy Tudor wood-beamed houses.
Day 10: Alfriston to Eastbourne 11 miles
Today’s walk is possibly the highlight of the whole of the South Downs Way. The day’s walking starts with following the Cuckmere Valley down to the coast, then along the top of the Seven Sisters, a line of chalk cliffs, to Birling Gap and Beachy Head. Then all too soon you find yourself in Eastbourne
Optional Day(s) in Eastbourne:
There is so much to see in Eastboure and the surrounding area that it is worth spending an extra day/s to take in the beach and explore.
Day 11: Depart after breakfast
Depart after breakfast or extend your holiday walking and spend some time exploring the Eastbourne area.
We can transfer you to your car or station.
Please note the following events take place at Goodwood:
Goodwood Festival of Speed will take place from Thursday 10th to Sunday 13th July 2025.
The Qatar Festival (Gorious Goodwood) will take place from Tuesday 29th July to Saturday 2nd August 2025.
Goodwood Revival will take place from Friday 12th to Sunday 14th September 2025.
These events affects the availability of accommodation in the area of Goodwood and our ability to deliver your luggage (days 4 and 5 of the itinerary).
Therefore when booking your walking holiday on the South Downs Way we suggest you avoid these dates.
Winchester to Eastbourne
in England UK
11 day itinerary
9 days walking and 10 nights
Suggested Itinerary
| Day 1: | arrive Winchester | |
| Optional Day: | optional extra day in Winchester | |
| Day 2: | Winchester to Exton | 12 miles |
| Day 3: | Exton to Clanfield | 8 miles |
| Day 4: | Clanfield to Cocking | 15 miles |
| Day 5: | Cocking to Amberley | 12 miles |
| Day 6: | Amberley to Steyning/Bramber | 13 miles |
| Day 7: | Steyning to Pyecombe | 7 miles |
| Day 8: | Pyecombe to Lewes | 10.5 miles |
| Optional Day: | optional extra day in Lewes | |
| Day 9: | Lewes to Alfriston | 12 miles |
| Day 10: | Alfriston to Eastbourne | 11 miles |
| Optional Day: | optional extra day in Eastbourne | |
| Day 11: | depart Eastbourne |
11 day itinerary 10 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2025 | £1,300 | £2,090 | £2.290 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Optional Accommodation Upgrades for
South Downs Way Walking Holiday
Winchester to Eastbourne
Can be added when booking online
Subject to availability Supplement per person per night
Winchester
Wykeham Arms
double/twin
£69.00
Single
please ask
Winchester Hotel
£54.00
please ask
Warnford (for Exton)
George & Falcon
double/twin
£30.00
Single
please ask
Bramber
Old Toll Gate Hotel
double/twin
£46.00
Single
please ask
Lewes
White Hart Hotel
double/twin
£46.00
Single
please ask
Alfriston
Deans Place Hotel
double/twin
£82.00
Single
please ask
Star Inn
£82.00
please ask
Eastbourne
Cavendish Hotel
double/twin
£59.00
Single
please ask
Grand Hotel
£85.00
please ask
Lansdowne Hotel
£56.00
please ask
What’s included
in your South Downs Way Walking Holiday in South England
- accommodation at high quality guest houses, inns or small hotels on a bed and breakfast basis
- room with en-suite or private bathroom, tea and coffee making facilities
- daily luggage transfer
- support should there be any problems on route
- detailed itineraries
- OS 1:25,000 map
- guide book to The South Downs Way
Optional Extras
for your South Downs Way Walking Holiday in South England
- upgrade to the region’s most elegant, prestigious and famous hotels, where available
- transfers back to car or station
- parking facilities
- rest days
- inn to inn walks
What’s not included
in your South Downs Way Walking Holiday in South England
- lunches and dinners
- travel insurance
Lunches and Dinners
These are not included.
Evening meals
These are available at overnight locations, either at your accommodation or in the town/village.
Packed lunches
These can be provided by your accommodation or can be obtained from a local store, or cafe or inn along the route.
Holiday Travel Insurance
We require that you take out holiday insurance as Let’s Go Biking Ltd accepts no liability for the following:
cancellation, personal accident, illness, loss/theft of personal possessions and/or money, and any unforeseen circumstances, especially travel delays.
This is in addition to our existing
booking conditions.
Please contact us if you have any questions.
Our telephone Lines are open 7 days a week.
UK +44 (0)1837 880075
or +44 (0)207 193 1252
March to September 9am to 9pm
October to February 9am to 5pm
US +1 (646) 233-1541
New York 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
AUS +61 (02) 8006 0182
Sydney 10 hours ahead of UK time:
March to September 7pm to 7am EADT
October to February 7pm to 3am EADT
CAN +1 (647) 4786251
Toronto 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
or
South Downs Way Walking Holiday:
How to get there:
- By Plane to London, Gatwick, Bournemouth or Southampton where we can arrange transfer to the start of your walk
- By Car to Winchester area where parking is available
- By Train/Bus to Winchester or Eastbourne
This 100 mile walking holiday is along the South Downs Way from Winchester to Eastbourne.
This is one of our Southern England Walking Holidays, and also one of our National Trail Walking Holidays.
We offer National Trail walking holidays in England and Wales in the UK.
This is one of our categories of walking holidays.
- Cleveland Way
- Cotswold Way
- Cumbria Coastal Way part of the England Coast Path
- England Coast Path
- Glyndwrs Way in Wales
- Hadrians Wall Path
- Norfolk Coast Path part of the England Coast Path
- North Downs Way
- Offas Dyke Path in Wales
- Peddars Way
- Pembroke Coast Path part of the Wales Coast Path
- The Ridgeway
- South Downs Way
- South West Coast Path part of the England Coast Path
- Thames Path
- Yorkshire Wolds Way
