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Home โ†’ Blog โ†’ South Downs Way Walking Holidays: Route Overview Winchester to Eastbourne
Article overview
  • Covers the full 100-mile South Downs Way route from west to east
  • Breaks the trail into daily walking stages with distance and highlights
  • Offers tips on where to stop, what to see, and how to pace your walk
  • Includes beginner-friendly advice, route variation options, and rest days
  • Ideal for planning a self-guided holiday with or without luggage transfer

Why Walk the South Downs Way?

The South Downs Way is one of Britainโ€™s most accessible and rewarding long-distance walking routes. Stretching approximately 100 miles from Winchester to Eastbourne, it offers a diverse blend of rolling countryside, historic villages, panoramic hilltop views and dramatic cliffside trails.

What makes this route so appealing is its flexibility. Whether youโ€™re walking the full distance over 8โ€“10 days or tackling it in sections, the infrastructure is solid, the terrain is forgiving, and the scenery constantly changing. From Iron Age forts to sea cliffs, thereโ€™s no shortage of reasons to explore this National Trail on foot.


Route Overview: Winchester to Eastbourne

Letโ€™s break down the South Downs Way into practical, walkable stages. This guide is based on a west-to-east route (Winchester to Eastbourne), which is the more popular direction due to prevailing winds being at your back.

Stage 1: Winchester to Exton (12 miles)

Starting at the cityโ€™s bronze National Trail sculpture, the route quickly transitions from historic urban streets to open countryside. Youโ€™ll pass through the Itchen Valley, cross rolling farmland, and reach the peaceful village of Exton. Itโ€™s a gentle introduction with well-marked paths and steady terrain.

Stage 2: Exton to Buriton (11 miles)

This stage includes Butser Hill, one of the highest points on the trail, offering expansive views over the surrounding countryside. Youโ€™ll also walk through Queen Elizabeth Country Park, making this a varied and scenic day. Buriton is a tranquil end-point with character and good accommodation options.

Stage 3: Buriton to Cocking (12 miles)

A quieter section through woodland and over chalk ridges. Highlights include Harting Down and Beacon Hill. This part of the route is particularly good for wildflowers in spring and early summer. The village of Cocking has limited facilities but is often served by transfer services from nearby towns.

Stage 4: Cocking to Amberley (12 miles)

Expect dramatic ridge walking and some of the best views on the entire route. Youโ€™ll pass Bignor Hill and descend toward the River Arun. Amberley is one of the most picturesque villages on the trailโ€”ideal for an overnight stop and pub dinner.

Stage 5: Amberley to Steyning or Bramber (12 miles)

This leg features rolling farmland and open tracks. Itโ€™s a more undulating section, and youโ€™ll cross the River Adur towards the end of the day. Bramber and nearby Steyning both offer excellent places to stay, eat and resupply.

Stage 6: Steyning to Pyecombe (8 miles)

A shorter day, often used as a recovery stage. Youโ€™ll pass through Devilโ€™s Dyke, one of the most dramatic dry valleys in southern England. Pyecombe has limited accommodation, so many walkers opt for a transfer to nearby villages or Brighton.

Stage 7: Pyecombe to Southease (13 miles)

This section includes Ditchling Beacon and a stretch of high ridgeline walking. On clear days, youโ€™ll see as far as the Isle of Wight and the Weald. The descent into the Ouse Valley is gentle, and Southease station connects easily to Lewes or Brighton for optional detours or overnight stays.

Stage 8: Southease to Alfriston (7 miles)

A short but scenic day through open downland, finishing in the charming village of Alfriston. This is a great place for a rest day, with galleries, teashops and river walks to enjoy. Itโ€™s also a chance to prepare for the final, more dramatic coastal stage.

Stage 9: Alfriston to Eastbourne (11 miles)

The final section is arguably the most iconic. After passing through West Dean and climbing up to the coast, youโ€™ll walk the clifftop trail over the Seven Sisters and Beachy Head. Itโ€™s a grand finaleโ€”windy, exposed, and unforgettable. The route ends at Eastbourneโ€™s western promenade marker.


Tips for Planning Your Route

Planning a successful South Downs Way walking holiday means more than just mapping the trail. Consider pacing, rest options, and your personal comfort level.

Adjusting for time and fitness

  • 6โ€“7 day itineraries are available but involve 15+ mile days, which may be tiring for first-time walkers

  • 9โ€“10 day itineraries offer a slower pace with more time for rest and sightseeing

  • Short breaks (2โ€“4 days) covering highlight sections are ideal for those testing the waters

Where to rest

Alfriston and Amberley are popular rest day spots, offering cultural interest and good dining. A mid-walk rest day can help reduce fatigue and increase enjoyment.

Going east to west?

Some walkers prefer starting in Eastbourne and finishing in Winchester for a more gradual build-up, but it means walking into the prevailing wind and ending away from the sea. Choose based on your personal preference for scenery and pacing.


South Downs Discovery Route Options

South Downs Discovery offers a variety of self-guided holiday packages tailored to different durations and abilities. A classic itinerary covers the full trail in 8 days, with pre-booked accommodation, luggage transfer and detailed route notes.

Highlights include:

  • Flexible durations from 5 to 10 days
  • Optional rest days in key locations
  • Local customer support and 24/7 emergency line
  • Digital and printed trail maps
  • Baggage transfers between every stop

This removes the need to plan every detail yourself, allowing you to enjoy the trail without logistics getting in the way.


What to Expect on the Trail

Terrain

Mostly firm, chalky paths and grassy ridgelines. A few steeper sections, particularly near Butser Hill and Beachy Head, but nothing technically difficult.

Weather

Expect a mix of sunshine, wind, and occasional rain. The Downs are exposed in places, so waterproofs and sun protection are both essential.

Navigation

Waymarking is excellent. The trail uses acorn markers and fingerposts. A printed map or GPS app is helpful but not mandatory.

Food and drink

Villages every 10โ€“15 miles offer pubs, teashops and village stores. Some stretches require packed lunches, especially on Sundays or off-season.


Ready to Walk the Trail?

The South Downs Way is more than a trailโ€”itโ€™s a journey through time, nature and some of the UKโ€™s most celebrated countryside. Whether you want the full 100-mile experience or a carefully chosen highlight section, itโ€™s a route that rewards every step.

If youโ€™re looking for a walking holiday that combines manageable distances, strong infrastructure and sweeping views, this is your sign to start planning.


Walk the South Downs Way With Ease

Let South Downs Discovery take care of the logistics while you focus on the adventure.

We offer self-guided walking holidays from Winchester to Eastbourne with flexible durations, daily baggage transfer and hand-picked accommodation.

Start planning your perfect South Downs Way walking holiday today.

Paul Allshire

I run South Downs Discovery from start to finish - planning, booking and making sure everything runs smoothly. I know the trail inside out, from the best views to the cosiest pubs, and Iโ€™m here to help you enjoy every step.