South Downs Way Walking Holidays

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.

The trail stretches for around 100 miles from historic Winchester in Hampshire to the coastal resort of Eastbourne in East Sussex.

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..

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.

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.

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.

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.

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.

Absolutely! We are very flexible and will work with you to plan the perfect itinerary at your own pace.

Yes, we offer discounts for groups of 4 people or more. The larger the group, the bigger the discount!

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.

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.

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.

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.

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.

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.