Route: From Winchester to Eastbourne


The South Downs Way gives you a taste of the extensive history and the geology of the South of England. Winchester, Hampshire on the edge of the South Downs National Park is your starting point. Once the county seat of the Wessex Kings, Winchester is home to many medieval sites, and may be worth an extra night to give you a chance to explore this historic city before setting off on your adventure.  Once out on the path you have the chance to experience the wide skies and beautiful landscape, with a mixture of rolling hills, woodland and open patchwork fields knowing that this is a land well-trodden from the Bronze Age to the present day. Evidence of habitation abound, with barrows, Iron Age forts, the Roman trackways, Saxon and Norman churches and castles, windmills intermingle with ancient beacon points as you make your way through the pretty Downs villages of Cocking, Amberley and Alfriston on  your way to the seaside town of Eastbourne.


All our holiday packages include:

  • Overnight accommodation staying at carefully selected B&Bs, Inns and Hotels
  • A detailed holiday pack
  • Luggage transfers
  • Transport from path to accommodations if necessary
  • Maps
  • Guidebook
  • Emergency support.


Our holiday packages do not include:

  • Transport to and from the start and end of the holiday, unless stated.  We can help you with your options.
  • Packed Lunches and Evening Meals
  • Travel Insurance

Itinerary & Costs

A spectacular 100 mile walk stretching across the chalky rolling hillsides of Southern England, from the historic cathedral city of Winchester the South Downs Way wends its way through picture postcard villages onwards to the seaside town of Eastbourne, Sussex. A picturesque and relaxing trek for walkers of all levels of experience.

The Daily Itinerary

Click on a day for further information.

Day 1: Arrive
Day 2:
Winchester to Meonstoke
Distance: 13 miles
Day 3:
Meonstoke to South Harting
Distance: 16.5 miles Difficulty: Easy/Moderate
Day 4:
South Harting to Amberley
Distance: 20 miles Difficulty: Easy/Moderate
Day 5:
Amberley to Bramber
Distance: 14 miles Difficulty: Easy/Moderate
Day 6:
Bramber to Kingston-near-Lewes
Distance: 19 miles Difficulty: Easy/Moderate
Day 7:
Kingston-near-Lewes to Alfriston
Distance: 11.5 miles Difficulty: Easy/Moderate
Day 8:
Alfriston to Eastbourne
Distance: 10.5 miles
Day 9: Depart

What's Included

  • Accommodation for the length of your holiday including the night before you start walking and the evening after your final day's walking in good quality B&Bs, Inns and small hotels. This will be en-suite wherever possible.
  • Breakfast - This may be a full cooked or continental option depending on accommodation. Evening meals can be arranged with certain accommodations for an additional charge.
  • A Personalised Holiday Pack containing maps and addresses for accommodations, pick up points and daily mileage information.
  • Luggage transfers between each accommodation. 1 bag per person up to 20 kilograms. Additional bags can be added upon request.
  • If required, path to accommodation or round river transfers (free of charge)
  • Phone line support between the hours of 0900-1900, 7 days a week for the length of your holiday.

Optional Extras

The following items are optional and can be removed to reduce the cost of your holiday.

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Important Information


5/5 Elke Maldar
very helpful in every way, accommodation perfect, luggage transfer very good. Easy booking process. Information pack very good.
4/5 Scott Harradine, Canada
Will use Walk the Trail again and recommend them without hesitation. | My contact Linda was a treat to work with and owner Mike fixed an on-the-walk issue immediately and thoroughly.
5/5 Trusted Customer
The best for civilized walking. | The great benefit was their planning which enabled us to reach each B & B within our capabilities and in a reasonable time. Yes we would use them again.
5/5 Brian Davey
Concise clear info pack with all the detail I needed. Great accom. The only time I ever got into slight ‘trouble’ was not knowing which end of a village I had arrived at (my own fault- I refused to use Komoot :-) and only used cellphone GPS when completely baffled)
Holiday Summary



7 Days / 8 Nights 15 miles daily avg


Rating: 3


Number in Group: 2

What's Included
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Cost £1,071 per person

Based on Two people sharing a Double or Twin Room

Total Cost £2,142

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