The unforgettable South Downs Way runs for 100 miles along ancient routes and droveways on the chalk escarpment and rounded ridges between Winchester and Eastbourne on the south coast of England. Its natural beauty is glorious and unspoilt, no wonder almost the entire route is within a protected National Park. History and panoramas are at every turn and yet the walk is peaceful, silence is golden broken only by skylarks and peewits, sheep quietly grazing, hares racing through scrub and orchids or perhaps a horse threading along the track. Villages, even less towns, are few and far between - snuggling at the foot of the downs but just enough to call you down for refreshment and rest.

Our walking holiday includes a lovely mix of luxury 2 night stays which we are thrilled to offer and transfers where needed to the start or end of the day's walking. We guarantee a breath taking experience!

Holiday details



from £3,815 per person

Based on two people sharing a room

What’s included?

Transfers to the start and end of walks as needed.  See what’s included as standard


9 nights

Start & Finish

Starts Mondays in Winchester and finishes Eastbourne. Winchester is 1 hour and Eastbourne is 1.5 hours by train from London.



Two night stays at a castle, two 4* hotels and a 15th Century inn with a final night at a 5* hotel

Holiday type


This tour is priced without a guide and you are free to explore on your own.  If you would like a guide for part or all of your trip, we are happy to provide a knowledgeable, local guide

Activity level

Not so gentle walking. More info...


8 days of walking 11 - 15.5 miles (17- 25 km) per day


Ridge walking on rolling downs


  • add an extra day in Bepton to play tennis on your hotel's grass courts, visit the extraordinary Weald and Downland Living Museum at West Dean and the wonderful gardens at Woolbeding
  • add an extra day at Amberley Castle for a day off and a visit to Arundel Castle
  • split days 5,7 and 8 into 2 making a 12 night trip

Itinerary day-by-day


  1. 1. Day one

    Arrive Winchester

    Arrive in Winchester on Monday and settle into your hotel in the heart of this historic city. Founded in 450 BC and the capital of Saxon England, enjoy the cathedral and many other fine buildings whilst strolling along Winchester's winding streets. It's a fun place to explore! You Host will meet you this evening to run through your itinerary and share their local knowledge.

  2. 2. Day two

    Winchester to Exton

    From the Old City Mill at the core of Winchester, your walk quickly meets open fields and climbs onto the rolling downs with expansive views - your landscape home for the next week. Blow away the cobwebs and revel in glorious, rural, unspoilt England. Easy walking takes you through the occassional hamlet and wood, past farms and hilltops to Exton where we meet you and transfer you back to your hotel in Winchester.

    12 miles (19 km)

  3. 3. Day three

    Exton to Buriton

    Starting in Exton, today includes the highest point of the South Downs at Butser Hill and several panoramic viewpoints with carpets of yellow cowslips at your feet in April and May. You also encounter the pretty chalk Meon River, famed for its trout fishing, coombs a plenty and protected countryside noted for its butterflies and orchids. It's a dream day and we meet you in the unspoilt village of Buriton for a transfer to your next hotel.

    13.5 miles (22 km)

  4. 4. Day four

    Buriton to Bepton

    Your walk briefly has a different feel this morning as it crosses lowland meadows dissected by hedgerows. You then climb again onto the soaring Sussex downs replete with cowslips and orchids. Think chalk downs and coombs - ups and downs, long views, lots of woods and a day when you need a packed lunch as you are far from the madding crowd. Not far beyond Linch Down you leave the Way and follow tracks down into Bepton to your hotel for a 2nd night.

    11 miles (17 km)

  5. 5. Day five

    Bepton to Amberley

    Walking from your hotel, a patchwork of woods and meadows are dotted with brick and flint farm dwellings and a section of the Roman Road known as Stane street which linked Chichester to London. Think back to AD 70 as you walk it in its climb over the South Downs. Enjoy grand vistas and pack a lunch as this is remote country with watering holes only below the Downs. The Way descends at the end of your day and crosses the sinuous River Arun into the beautiful village of Amberley where you can walk to Amberley Castle your wonderful overnight stay.

    15 miles (24 km)

  6. 6. Day six

    Amberley to Botolphs

    Ascending up to the Downs from Amberley Castle, listen for the skylarks and peewits and spot the occassional hare - otherwsie sheep and cattle are the order of the day or large cropped fields, fringed with woods. As ever, binoculars are worth the carry - the English Channel is visible at several points. The dry valley at Washington forces you downhill and back up again, but here is the only watering hole of the day. Chanctonbury Ring, marked by beech trees is a high point beyond before you amble down at the end of the day to the hamlet of Botolphs where we meet you and transfer you to Amberley for a second night there.

    13 miles 921 km)

  7. 7. Day seven

    Botolphs to Housedean Farm

    Today is fascinating - wonder at Britain's largest chalk coombe or steep sided dry valley known as the Devils' Dyke and the authentic farm buildings in Saddlescombe village which has been farmed for 700 years. Then there's Jack and Jill, the pair of photogenic windmills, the Roman haunt below Ditchling Beacon and the hill where Richard II was challenged in the 13th Century. What a walk through history and beauty! We meet you at the end of the day and transfer you to the pretty village of Alfriston for the first of two nights there.

    15.5 miles (25 km)

  8. 8. Day eight

    Housedean Farm to Alfriston

    Grand spaces abound again today with the natural beauty of the area ever present. History abounds as you walk Juggs Road where fishermen hauled their catch over the downs, dew ponds - created to hold water for animals in an otherwise porous chalk region and several properties where the Bloomsbury set lived - the colourful and alternative painters and writers who frequented the area in the early 1900s. The walk drops steeply to cross the River Ouse and then there's the paragliders on Bostal Hill as the Way curls south signalling its end at the nearby coast. You walk directly into chocolate box Alfriston with its brick and flint walls and timber framed inn for a 2nd night at the 15th Century Star Inn.

    14 miles (22 km)

  9. 9. Day nine

    Alfriston to Eastbourne

    Your last day of walking is the most spectacular as you start out along the Cuckmere River. Then take a hilly path onto the roller coaster cliff top walk along the Seven Sisters, the white cliffs, and over Beachy Head. What a fantastic vista as you finally reach the coast and descend for the last time, into old fashioned Eastbourne. Sink into the luxury of your beach front hotel - a fitting finale for a wonderful achievement!

    12 miles (19 km)

  10. 10. Day ten

    Depart Eastbourne

    Splash in the sea, enjoy a dip in your hotel pool and depart Eastbourne at leisure - but not before you've had one of its famous ice creams.