South Downs Way Walking Holidays
South Downs Discovery self-guided walking holidays.
Browse holidays - from £335pp
South Downs specialists who know this National Trail inside out!
Our perfectly planned self-guided walking holidays cover the full 100 miles or so of the trail from Winchester to Eastbourne with options from six to ten days. We also provide shorter routes that range from two to five days and focus on different sections of the South Downs Way.
What makes the South Downs so special?
What truly sets the South Downs Way apart is its variety. Over the course of the trail, the landscape subtly changes, offering a different experience almost every day.
Walkers can expect:
- Long, open ridges with panoramic views across farmland, woodland and river valleys
- Quiet stretches of chalk downland rich in wildflowers and wildlife
- Traditional villages with historic pubs, churches and local character
- Ancient hill forts and archaeological sites that hint at the area’s deep history
- A spectacular coastal finale, with sweeping views over the Seven Sisters and the English Channel
South downs walking holiday highlights:
- Iconic chalk cliffs at Seven Sisters & Beachy Head
- Cathedral city of Winchester, the ancient capital of the kingdom of Wessex & early England
- Historic towns of Arundel & Lewes
- Picturesque villages like Buriton, Amberley & Alfriston
- Historic landmarks such as Winchester Hill, Chanctonbury Ring and Devil’s Dyke
- Panoramic views from the South Downs ridgelines towards the North Downs inland and out to sea
The South Downs Way boasts the claim to fame that it is the only UK national trail that is entirely within a national park. Despite its length, the trail never feels remote or intimidating. You’re never far from a village, a place to eat or a comfortable bed for the night.
For more information on our South Downs Way walking holidays email us at info@southdownsdiscovery.com or call us on +44 (0)1323 396215
Customer reviews
6 to 10 day walking holidays
Full South Downs
Way holiday routes
These routes cover the full 100 miles or so from Winchester to Eastbourne through the South Downs National Park. Walk through rolling countryside, pretty villages and spectacular river valleys along the River Cuckmere and River Arun before reaching the dramatic Seven Sisters and Beachy Head on the south coast. Choose your ideal pace from six to ten walking days, with daily luggage transfers and excellent accommodation included throughout.
6 days
106 miles / 171 km
6 days Walking
Winchester to Eastbourne
- 106 miles / 171 km
- Averaging 18 miles / 29 km per day
- Booking code SDW6
7 days
103 miles / 166 km
7 days Walking
Winchester to Eastbourne
- 103 miles / 166 km
- Averaging 15 miles / 24 km per day
- Booking code SDW7
8 days
105 miles / 169 km
8 Days Walking
Winchester to Eastbourne
- 105 miles / 169 km
- Averaging 13 miles / 21 km per day
- Booking code SDW8
9 days
106 miles / 170 km
9 Days Walking
Winchester to Eastbourne
- 106 miles / 170 km
- Averaging 12 miles / 20 km per day
- Booking code SDW9
10 days
110 miles / 177 km
10 Days Walking
Winchester to Eastbourne
- 110 miles / 177 km
- Averaging 11 miles / 18kms per day
- Booking code SDW10
2 to 5 day walking holidays
Shorter South Downs Way
holiday routes
Perfect for those with limited time, these shorter breaks let you experience different sections of the South Downs Way. Walk two to five days along selected parts of the trail, where stunning scenery is guaranteed in this area of outstanding natural beauty. Each route includes great quality accommodation, daily luggage transfers and detailed route notes that guide you along the trail.
2 days
22 miles / 36 kms
2 Days Walking
Eastbourne Circular via Alfriston
- South Downs Way inland & coastal route
- 22 miles / 36 kms,
- Averaging 11 miles / 18 km per day
- Booking code EC2
3 days
39 miles / 63 kms
3 Days Walking
Poynings to Eastbourne
- 39 miles / 63 kms
- Averaging 13 miles / 21 km per day
- Booking code PE3
3 days
47 miles / 75 kms
3 Days Walking
Winchester to Amberley
- 47 miles / 75 kms
- Averaging 16 miles / 25 km per day
- Booking code WA3
4 days
48 miles / 77 kms
4 Days Walking
Winchester to Amberley
- 48 miles / 77 kms
- Averaging 12 miles / 19 km per day
- Booking code WA4
4 days
56 miles / 90 kms
4 Days Walking
Amberley to Eastbourne
- 56 miles / 90 kms
- Averaging 14 miles / 22 km per day
- Booking code AE4
5 days
58 miles / 93 kms
5 Days Walking
Amberley to Eastbourne
- 58 miles / 93 kms
- Averaging 11 miles / 18 km per day
- Booking code AE5
Why choose a South Downs Way walking holiday with us?
Here at South Downs Discovery we know everything there is to know about the South Downs and we’re more than happy to share our passion for this beautiful part of southern England with you! With many years of experience walking through this beautiful national park (not to mention testing out all the pubs along the way!) our first-hand knowledge is hard to beat.
What's included?
Each and every South Downs Discovery walking holiday includes a carefully planned itinerary with detailed route information, so all you need to focus on is the walk!
We provide high quality accommodation on a B&B basis and reliable luggage transfers each day. You’ll also receive a comprehensive pre-departure pack containing personalised trip notes with insider tips, an annotated OS map booklet, a detailed guidebook, and luggage labels. For lunch and dinner, we ‘ll give you recommendations for the best local pubs and restaurants along the South Downs Way.
About South Downs Discovery
We’re a dedicated walking holiday company and we specialise exclusively in the South Downs Way. Our team is passionate about putting together high quality, self-guided walking holidays that showcase the very best that the South Downs has to offer, with its fascinating history and outstanding natural beauty.
We pride ourselves on our outstanding levels of customer service which the online reviews from our many happy customers will attest to!
The South Downs Way Route
Explore the full route from Winchester to Eastbourne on this interactive map.
Frequently Asked Questions
We’ve answered some of the most common questions about the South Downs walking tours.
What is the South Downs Way?
The South Downs Way is a 100 mile national trail in southern England and is the only one in the UK which is entirely situated within a national park. It stretches from the historic city of Winchester to the Victorian seaside town of Eastbourne on the south coast. It’s popular with walkers, horse riders and cyclists, offering spectacular views of the rolling countryside, dramatic clifftop walks over the chalk escarpment and panoramic views vistas towards the English Channel & towards the North Downs inland.
How long is the South Downs Way?
The trail stretches for around 100 miles from historic Winchester in Hampshire to the coastal resort of Eastbourne in East Sussex.
How many days does it take to walk the South Downs Way?
The full 100 mile trail typically takes six to ten walking days, depending on your pace. Our longer routes offer shorter daily distances with more time to explore some of the pretty villages and classic pubs along the way. If you have limited time, our two to five-day options cover specific sections of the route..
What are the main highlights of the South Downs Way?
The National Trail features the dramatic Seven Sisters and Beachy Head chalky cliffs with wonderful views out to sea. You’ll walk through picturesque villages with thatched cottages and pass high points such as Devil’s Dyke, Ditchling Beacon and Beacon Hill that offer far-reaching views across rolling countryside. The route takes you through beautiful river valleys and starts at Winchester, the cathedral city and England’s ancient capital, before finishing at the south coast resort of Eastbourne.
What is the most scenic section of the Souths Downs Way?
The eastern section that includes the Seven Sisters chalk cliffs and Beachy Head is particularly dramatic, with stunning coastal views. However, the entire National Trail offers amazing natural beauty, from rolling countryside and field paths in the western sections to spectacular viewpoints such as Harting Down and Ditchling Beacon throughout the route.
Is the South Downs Way suitable for beginners?
Yes! The trail is well-marked and offers a mix of gentle and more challenging sections along the chalk escarpment and river valleys. Walkers of all levels can enjoy the scenic route safely and at their own pace.
What accommodation do you use?
We understand that comfortable accommodation is what makes the difference between a good walking holiday and a great one. We use a mix of good quality B&Bs, hotels and pubs. You don’t need to pay a deposit until everything is booked which means you’ll see where you are staying before you need to pay anything.
We personally visit all our accommodation providers and constantly monitor customer feedback and online reviews.
What is included in our walking holidays?
Our self-guided walking holidays include handpicked accommodation with en suite or private bathrooms, breakfast, luggage transfers, luggage labels, personalised trip notes with insider tips, an OS map booklet with all your accommodation and points of interest marked on it, a Trailblazer guide book and out of office hours support during your trip.
Can I customise my walking holiday?
Absolutely! We are very flexible and will work with you to plan the perfect itinerary at your own pace.
Are group discounts available?
Yes, we offer discounts for groups of 4 people or more. The larger the group, the bigger the discount!
What level of fitness is required for the routes?
You don’t need to be an athlete, but a decent level of fitness will make your walk more enjoyable. The route inevitably means quite a few ups and downs through the stunning English countryside, so being comfortable with hill walking and appropriate daily distances is a good idea.
What meals are included?
Breakfast is included to get you started for the day. For lunch and dinner, we’ll give you some great recommendations for fine pubs and places to eat along the way.
Is there a luggage transfer service?
Yes, luggage transfer is included. Your bags will be collected each day no earlier than 9am and dropped off no later than 4:30pm but usually much earlier.
What should I pack for the walk?
Think comfortable and practical. Good walking shoes, weather appropriate clothes including waterproofs and a daypack for essentials. Don’t forget a water bottle, hat, sunscreen and snacks for the trail.
What is the best time of year to walk the South Downs Way?
The best time is from spring to autumn (April to October), although UK weather is notoriously hard to predict! Bank holidays can be busier along the route.
How do I book a walking holiday?
It’s easy! You can book directly on our website or give us a call or email. We’ll help you plan the perfect walking holiday, then check availability for your preferred dates and get you booked in. You don’t need to pay anything until it’s all booked and confirmed and you have seen where you will be staying.
