Winchester to Canterbury Pilgrims way

“Walk the length of one of England’s most historic trails, the Pilgrim’s Way, on this two-week self-guided walking holiday from Winchester to Canterbury. ”


Winchester | Canterbury | Pilgrims’ Way | Luggage transfer | Personalised support | Maps and route details provided | Optional: Extra day in Canterbury, fully marked up OS Maps

Description of Winchester to Canterbury Pilgrims way

This two-week self-guided walking holiday has been designed specifically for those wishing to undertake the whole of the Pilgrims' Way between Winchester and Canterbury, which is 130 miles over 14 days.

The tour is arranged for you including high standard hotel and historic inn accommodation, breakfast and luggage transfer each day. Lunches and evening meals are not included, however there will always be a nearby restaurant open, or food available in your hotel or inn on the night of your stay. You will be met on arrival so that the walk and your route can be discussed and any questions answered. You will have on-the-phone support available to you throughout your walk and your progress along the trail will be tracked every day to ensure all is going to plan.

Most hikers add an additional day so they have time to explore the beautiful medieval city of Canterbury and this can be arranged for an additional charge. Should you require it, the 10 OS Explorer maps (1:25000 scale) supplied can be marked up to show your route and accommodation for an extra charge.

This walk can start at any time of the year subject to availability.

Travel Team

If you'd like to chat about this holiday or need help finding one we're very happy to help. The Travel Team.

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Departure information

This trip can be tailor made throughout the year to suit your requirements

Responsible tourism

Responsible tourism: Winchester to Canterbury Pilgrims way


We are a family run ‘tour operator’ based in the Kent Downs Area of Outstanding Natural Beauty (AONB) in the UK. We are committed to operating a Responsible Travel Policy (RTP) that is supportive and in sympathy with the local communities and environment within which we operate. This is in line with the stated aims on all our holidays that invites customers to ‘discover hidden Kent, its history and its people’.

We have been accredited as a Silver Tour Operator under the Green Tourism Business Scheme (GTBS) since 2006. We actively encourage all customers to use public transport to access the Kent Downs (AONB). We advise customers where they can purchase locally produced food and produce along the route of their walk and encourage them to use local services.

Experience the peace, the history and the beauty of these walking vacations in the UK.


Whilst on their walking vacation in the UK we also actively encourage customers to visit local social projects such as the Elham Valley Vineyards, run by the Vale of Elham Trust that provides work opportunities for people with learning disabilities. We also have encouraged people to walk the North Downs Way for the benefit of nationally recognized charities. Since 2002 we have organised charity walks on behalf of the many national charities including The Children’s Society, John Grooms and Christian Aid.

We have worked closely over the last four seasons with the Our Land project in conjunction with Responsible Travel and the Kent Downs AONB., helping to increase an awareness of what the local rural economy has to offer visitors to the Kent Downs Area of Outstanding Natural Beauty

The book, the 'Pilgrims Way Fact and Fiction of an Ancient Trackway' published by the History Press in 2011 came out of research undertaken to support Walk Awhile's walking holidays and bring together the various histories relating to the Pilgrims' Way. The original research for Derek Bright's book was peer reviewed by the Kent Archaeological Society and published as a KAS E-article in 2009.

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