• South Downs Way National Trail
    South Downs Way National Trail
    Footprints are the local South Downs Way Specialists. Over 25 years of experience and local knowledge.
  • Short Break Walking Holidays
    Short Break Walking Holidays
    Short Breaks on South Downs Way, Lewes to Eastbourne in the South Downs National Park
  • Walking Holidays on South Downs Way
    Walking Holidays on South Downs Way
    Devils Dyke to Chanctonbury Ring, what better place to holiday than the South Downs Way
  • Poppies on South Downs Way
    Poppies on South Downs Way
    Poppies bathing in a setting sun in South Downs National Park near Brighton
  • Oxbow Lakes at Cuckmere Haven
    Oxbow Lakes at Cuckmere Haven
    Stunning oxbow lakes at Cuckmere Haven within South Downs National Park
  • Arun Valley Amberley
    Arun Valley Amberley
    Sunset over Arun Valley and South Downs Way at Amberley
  • Birling Gap Sunrise
    Birling Gap Sunrise
    Last day of walking the South Downs Way. One of many highlights during our Annual Walk every June

South Downs Way Walking Holidays

We are based in Steyning, the midway point on the South Downs Way. We personally visit each and every Bed & Breakfast that we include as part of your holiday and are also very familiar with many of the pubs and restaurants we recommend. When you make an enquiry with us, we check that the rooms – it does get busy during high season – are actually available unlike some others and that when you place your booking with us you do get what was offered.

When you make an enquiry with us, we check that the rooms are actually available (unlike some other companies) and that when you place your booking with us you do get what was offered and what you expected!

We know this trail intimately; We have been organising walking holidays on the South Downs Way for over 25 years, and for the past 17 years we have been leading the Annual South Downs Way Walk each June between Winchester and Eastbourne.

Because of our local knowledge we routinely use B&Bs that are close to the trail. An exception to this is Lewes (offering excellent accommodation and choices for an evening meal), where uniquely we provide a taxi to get you safely off the trail and save having to walk the 2 miles into town or to a pub for your evening meal.

If you would like to see what previous walkers have said of our services then please click for HEREWe have over 10 years of feedback, but feel the most recent few years are the most pertinent…

If you don’t have time to walk the South Downs Way in its entirety on one of our self-guided walking holidays you can also do it in small chunks with our self-guided weekend / short break walking holidays.


The South Downs Way was officially opened as a national trail in 1972. It ran from the village of Buriton to Beachy Head high above Eastbourne. It faithfully followed the full 80-mile ridge of the southern chalk hills from their gentle rise at Harting Down to their dramatic departure beneath the English Channel. Some fifteen years later it was decided to extend the route back into Winchester, as such we offer both the original 80 mile trail and the full 100 mile trail over 7 (80 miles), 8 or 9 (100 miles) days as you see fit. We can of course offer you bite size chunks of the trail, split the trail in two, or even quarters and cover it with a series of Bank Holiday walks and see how the trail changes through the seasons.… the choice is yours!


Personally Tailored Walking Holidays

For our South Downs walking holidays we typically offer the following options:
Of course if you have a restricted schedule or would like to take a day or two out mid way then we are here to tailor and offer local advice.

9 Day Walking Holidays

Cover the full 100 miles of The South Downs Way from Winchester to Eastbourne
View Typical 9 Day Itinerary

8 Day Walking Holidays

Cover the full 100 miles of The South Downs Way from Winchester to Eastbourne
View Typical 8 Day Itinerary

7 Day Walking Holidays

Cover the 80 miles of The South Downs Way from Buriton to Eastbourne
View Typical 7 Day Itinerary


We can of course tailor all, or part of your holiday. Take a rest day midway and enjoy Steyning, Amberley or Lewes? We also have some of the Worlds finest Champagne Style Vineyards here now, Tinwood, Ridgeview & Rathfinny to name just three. We can add a rest day for you to visit these and of course taste their produce… Or if you think you have earned a day of luxury. why not stay at Amberley Castle (we run their history tours) or The Grand Hotel in Eastbourne? We will do everything we can to make your trip bespoke and tailored to your needs and wishes.

You can if you prefer, reverse the direction of your holiday and start your holiday in Eastbourne; however, we always recommend that you start at the Western end and walk with the prevailing winds to your back. You also have the aesthetic benefit of finishing your holiday with the magnificent ‘Seven Sisters’ coastal walk into Eastbourne.

Your average daily walking mileage along The South Downs will be around 12 miles. Depending upon your itinerary there are likely to be a a couple of shorter days and a couple of longer days of 14 or 15 miles.

Your first night’s accommodation will precede your first day’s walking. We do not routinely include accommodation on your last day’s walking unless requested, but can add extra nights accommodation and tailor the holiday to fit your requirements.


The highly rated B&B’s/Hotels we use are in the following locations – Winchester, Corhampton/Meonstoke, Clanfield/Buriton, Cocking & Midhurst, Amberley, Steyning/Beeding, Pyecombe, Lewes, Alfriston and Eastbourne.
We regularly inspect these B&B’s to ensure they provide suitable accommodation, refreshments and meals.

What is Included?

  • Accommodation on a high quality Bed & Breakfast basis
  • All rooms will have ensuite / private bathrooms
  • Shuttles on and off trail where the walk is too far off.
  • Daily baggage transfers along the trail to your next B&B
  • The ‘Cicerone’ route guide & map book
  • Wooden baggage labels
  • Our very own route notes and guides
  • Our very own pub and food listings
  • Peace of mind, knowing we are here on the trail, just a phone call away if you need help.

What Makes us Different?

  • The B&B’s we use along the South Downs Way have all been personally inspected by us
  • We check rooms exist before sending you holiday offers or taking bookings.
  • All the rooms are either ensuite or have private bathrooms for your sole use – no exceptions
  • We regularly review our customer feedback and react quickly to it, click here to see previous comments
  • If your accommodation is more than a short stroll from the trail we provide transport. We don’t like road walking
  • We are based on the South Downs Way
  • We like to personally meet all our guests during their holiday
  • We actually walk the South Downs Way ourselves every June

What Will it Cost?

  • 7 day South Downs Way walking holiday from £755
  • 8 day South Downs Way walking holiday from £825
  • 9 day South Downs Way walking holiday from £895

Prices are per person and based on two people sharing a room. We will of course offer holidays to solo walkers and as a price guide you should add somewhere in the region of £40 per night. Prices are guides and based on rates for 2019 season.

Our self-guided walking holidays are offered under our trading name ‘Pear Tree Tours‘.