Bespoke Walking Holidays with Footprints of Sussex

Walking Holidays with  Accommodation

South Downs Way walking holidays – with bed & breakfast accommodation and baggage transfers included – are available throughout the year from our sister website Footprints of Sussex.

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

We have been organising walking holidays on the South Downs Way for 20 years and for the past 10 years we have been leading the Annual South Downs Way Walk each June between Winchester and Eastbourne and we know this trail intimately.

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.

Tailored Walking Holidays / Short Breaks

For our South Downs walking holidays we typically offer 8 or 9 night walking holidays covering the full 100 miles of The South Downs Way from Winchester to Eastbourne or 7 night walking holidays covering 80 miles along The original South Downs Way from Buriton to Eastbourne. We also offer short breaks and weekends.

We can of course tailor all, or part of, your holiday. Take a rest day midway and enjoy Steyning or Amberley? Do half now and the other half later in the year? Your holiday, your choice… We will do everything we can to make your trip bespoke and tailored to your needs and wishes.

You can, if you prefer to, reverse the direction of your holiday and start your South Downs walking holiday in Eastbourne; however, we always recommend that you start at the Western end and walk with the prevailing winds to your back. Starting from the Western end of The South Downs Way also means you 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, though some legs can be slightly shorter or longer depending on your itinerary

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



About Your Accommodation

The highly rated B&B’s we use are in the following locations – Winchester, Corhampton/Meonstoke, Clanfield, Cocking, Amberley, Steyning/Beeding, Pyecombe, Lewes, Alfriston and finally 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
  • Ensuite / private bathroom
  • Daily baggage transfers along the trail to your next B&B
  • The 192 page ‘Trailblazer’ route guide
  • Baggage labels
  • Our very own route notes and guides
  • Unique restaurant and pub offers
  • Exclusive ‘South Downs Way’ cloth badges
  • Certificates confirming completion of the trail
  • Pear Tree Tours gifts
  • 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 inspected by us personally
  • 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
  • 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


Find out more about our South Downs Way self-guided walking holidays and make an enquiry by visiting the ‘Footprints of Sussex’ website