We specialise in high-quality, self-guided walking holidays along the South Downs Way. Using our expert, first-hand knowledge, we’ll take the hassle out of planning your trip. So whether you’re looking to walk the whole 100 miles of the trail from Winchester to Eastbourne or are just looking for a short break, you’ve come to the right place!
South Downs Walking Holidays
South Downs Discovery 2 to 10 day walking holidays.
Browse holidays - from £335pp
Self-guided walking holidays in the South Downs
Most Popular South Downs Walking Holiday Routes
We have built our reputation by providing a friendly and high-quality service that leaves nothing to chance. We are South Downs experts and each of us has personally walked every mile of the trail many times over. We do the (very enjoyable!) research so you don’t have to!
Everything is planned to the last detail, and we only work with good quality accommodation providers who specialise in South Downs Way walkers. We pride ourselves on our great service levels, but don’t just take our word for it! Check out our online reviews and see what our clients say about us.
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
from
£590/pp
See more details 5 days
56 miles / 90 kms
5 Days Walking
Amberley to Eastbourne
- 58 miles / 93 kms
- Averaging 11 miles / 18 km per day
- Booking code AE5
from
£715/pp
See more details 7 days
56 miles / 90 kms
7 Days Walking
Winchester to Eastbourne
- 103 miles / 166 km
- Averaging 15 miles / 24 km per day
- Booking code SDW7
from
£935/pp
See more details 8 days
56 miles / 90 kms
8 Days Walking
Winchester to Eastbourne
- 105 miles / 169 km
- Averaging 13 miles / 21 km per day
- Booking code SDW8
from
£1065/pp
See more details 9 days
56 miles / 90 kms
9 Days Walking
Winchester to Eastbourne
- 106 miles / 170 km
- Averaging 12 miles / 20 km per day
- Booking code SDW9
from
£1185/pp
See more details 9 days
56 miles / 90 kms
10 Days Walking
Winchester to Eastbourne
- 110 miles / 177 km
- Averaging 11 miles / 18kms per day
- Booking code SDW10
from
£1315/pp
See more details The South Downs Way
The South Downs Way is situated within the UK’s newest national park and was Britain’s first long-distance bridleway national trail. It stretches for 100 miles, from the historical splendour of Winchester to the coastal town of Eastbourne, just beyond the dazzling white chalk cliffs of the Seven Sisters and Beachy Head.
Walking the South Downs Way, you’ll follow an ancient trail that passes Iron Age hill forts, pretty villages and historic towns before reaching the Victorian seaside town of Eastbourne. Along the way, the trail offers spectacular views inland across the Sussex Weald towards the North Downs and out towards the sea at the eastern end.
This beautiful national trail winds through several beautiful river valleys, there’s also plenty of ridgeline walking as well and the scenery overall is extremely varied. The South Downs Way is often described as an ‘easy walk’ and it is in the sense that it’s well maintained with clear sign-posting. However there are lots of ups as well as downs so it’s not to be under estimated!
South Downs National Park
The South Downs became England’s newest national park in April 2011, officially recognised as an area of outstanding natural beauty and cultural heritage.
Stretching from Hampshire through west and east Sussex, England’s third biggest National Park incorporates over 600 square miles of some of the most beautiful countryside England has to offer. It’s easily accessible from cities like London & Brighton yet feels a world away from the hustle & bustle of those places. At times you’ll feel as though you have the Downs all to yourself but you’re never too far from civilisation!
The South Downs Way is the only national trail in the UK to be entirely situated within a national park and it stretches for around 100 miles from Winchester to Eastbourne.
