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South Downs – The Western Wander

4 DaysIconic LandmarkSelf-Guided


Walking Break


All Year


Self Guided


South Downs


Couples, Experienced Walkers, Family, Solo Walkers


Downland, Forest, Heathland, Meadow, Rivers

Walking Days



  • Winchester to Amberley
  • Stunning South Downs views
  • Historic landmarks
  • Delicious local food, wine and beer
  • Winchester cathedral
  • Nature reserves
  • Iron Age hill fort
  • Butser Hill
  • Queen Elizabeth Country Park
  • Bignor Roman Villa
  • Amberley Working Museum
  • Amberley Village
  • Virtual guide
  • Adventure Pack
  • Personal Service
  • Bag transfers
  • Full support

This magnificent walking break encompasses this stunning section of the South Downs Way, which starts in the historic city of Winchester and finishes at the quintessential village of Amberley nestled by the River Arun. 

With glorious views across Hampshire and Sussex, across to the North Downs and out across The Channel, this 77km route highlights many of the are historic treasures and natural beauty of the area, where historic tracks link with ancient woodland, tranquil river valleys, rich and diverse chalk downland, rolling farmland and picture postcard villages. The South Downs has many protected and diverse habitats which are home to unique wildlife, fauna, flora and make this place all the more special.

At the end of each day you will arrive at your accommodation with a choice of pubs and restaurants for dinner.  After breakfast, its time to head out onto the trail with your Virtual Guide on a GPS route for guidance and keeping you informed of points of interest along the way. In the meantime your bags will be transferred to your next overnight accommodation and will be ready for your arrival.  

You will be spoiled for choice for places to eat and drink along the trail. With welcoming pubs and restaurants, quaint sandwich shops, local artisan bakeries all awaiting you.  There will be numerous opportunities to sample local food, wines and beers along with our seasonal recommendations and try our special list of 'must taste delights'. 

What's Included

  •    5 nights handpicked en suite accommodation including breakfast.
  •    4 days walking
  •    Bespoke, individual service
  •    Virtual Guide & OS Maps App.
  •    Personalised itinerary
  •    Full route plan, trail notes, map, GPS
  •    Nature spotters guide
  •    Local history, heritage and geology info
  •    Treats for the walk
  •    Kids adventure pack (if required)
  •    Recommended refreshment stops
  •    Bag transfers
  •    Full support from our Sussex HQ before and during your trip 24x7

This adventure is ideal for the independent adventurer looking to escape either on their own, with a partner, family or group of friends where you all can reconnect and enjoy great walking, food, drinks and friendly accommodation.  

There are great transport links to Winchester, Petersfield and Amberley from London.

This adventure is flexible and available on a date to suit you (subject to availability) for a total of 4 walking days and 5 nights accommodation (additional nights are available if you would prefer to enjoy this route at a more leisurely pace , or if you would rather up the tempo and complete the route in less days - we can arrange this for you.  We are also happy to provide a customised itinerary if you would like to include some down days to enjoy local places of interest - we would be delighted to advise you on the numerous options available). This particular package works out at approximately on average 15 miles per day walking.). You will check into your first night's accommodation in Winchester on Day 1 to give you a chance to explore this fabulous cathedral city before you begin your walk the next day. Your last night will be spent in the delightful Sussex village of Amberley - with its castle and thatched cottages it is definitely one not to be missed! We strongly advise booking your trip in advance as places are limited. The trail can be enjoyed all year round.

Prices are based on a 'from' price, depending on accommodation type and availability. Accommodation is based on two sharing an en-suite room, staying on a bed & breakfast basis (single accommodation is available at a small supplement). You will receive a fully detailed itinerary, confirmation of your accommodation and a price quote. Once you confirm your booking, your price will be guaranteed with no additional surcharges.

With your bag transfers all taken care of, all you need to concentrate on savouring the views of the glorious corner of the country and putting one foot in front of the other.  You can have complete confidence that we will take care of your every need.

We are out and about in the South Downs every week guiding and instructing and we have walked the routes and trails many, many times. The area is like a second home to us, so you can be sure that you will be receiving the very best in terms of experience and expertise.  We work extremely closely with the National Park to ensure that all our trips, walks and activities are delivered sustainably and in line with their ethos.

Please do not hesitate to contact us if you would like to discuss your booking in more detail and we would be delighted to share our knowledge and passion for this stunning area with you to help ensure you have the perfect trip.