Winchester to Canterbury Pilgrims way

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


Winchester | Canterbury | Pilgrimsí 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 would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.

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 Ďtour operatorí 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 Ďdiscover hidden Kent, its history and its peopleí.

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 Childrenís 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.

1 Reviews of Winchester to Canterbury Pilgrims way

5 out of 5 stars

Reviewed on 03 Jun 2019 by

1. What was the most memorable or exciting part of your holiday?

The continual joy of being in natural areas, even if they were agricultural. Everything other than the sounds and the scents was secondary. Not very profound, I realize, but whereas I didn't plan it as a spiritual journey (I would have scoffed if you'd suggested it), it became that. Moreover, while most of the time, I had the paths to myself, I did meet some terrific people both on the paths and at the accommodations along the way.

2. What tips would you give other travellers booking this holiday?

I don't know what it was about the pilgrims on the North Downs Ways but they must have being doing penance for capital crimes because every time they saw a hill, they said "the flatland is well and good but let's climb this hill...and then descend again." Thus, what I thought would be a 120-mile trip turned into 158 and more grueling that I anticipated. No complaints, however, as I was afforded more sights but some travelers might be deterred by the lengths of the days. Thus, I think I'd make them aware that there are two options: (a) long and hilly and (b) shorter and flat

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

Financially? I don't know. As an American I was astounded by the extent of the footpaths and by the local reception and their desire to (a) preserve the lands and (b) make it accessible to others. I'm not sure that were I a farmer I'd welcome strangers traipsing through my backyard and across my pastures, spooking the cows and sheep and yet they were always welcoming. To my surprise, I read that rather than being bound by ancient laws, the complete footpath system is of recent vintage, dating essentially since WWII. Moreover, the British walk the footpaths themselves...and they are brisk walkers, I discovered.

4. Finally, how would you rate your holiday overall?

Excellent. I think that Jack and Mandy of the tour operator did a superb job in setting it up and in checking with me to see that everything was going well. If I had any complaints, it would be that while Surrey maintains the paths, Kent is less diligent. Signs are broken, some are obscured by brush, and thorny vines snag one as he passes. A bit of trail maintenance would go a long way towards improving the experience.

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