Pilgrims Way
Walking Holiday in
Southern England
Winchester to Canterbury
via Rochester
This is a 146 mile walking holiday on the Pilgrims Way from Winchester to Canterbury via Rochester.
This is one of our Hampshire Walking Holidays, one of our Pilgrimage Walking Holidays, and also one of our Southern England Walking Holidays.
Pilgrims Way Walking Holiday
A Pilgrimage walking holiday
in Southern England
from Winchester to Canterbury
via Alton, Guildford, and Rochester
We offer several itineraries for the 146 miles of Pilgrims Way walking holiday from Winchester to Canterbury via Rochester. This route follows the original Pilgrims Way used by travellers from the west of England and visitors from the continent who had arrived at Southampton or Portsmouth. This is a popular walking tour, so we have carefully selected comfortable accommodation to ensure you are well rested each night after a busy day hiking and sightseeing.
We offer 6 suggested itineraries for a Pilgrims Way walking holiday:
- 16 day walking holiday, Winchester to Canterbury, 146 miles
- 15 day walking holiday, Winchester to Canterbury without visiting Rochester, 137 miles
- 9 day walking holiday, Winchester to Oxted, 75 miles
- 9 day walking holiday, Oxted to Canterbury, 71 miles
- 11 day walking holiday, RELAXED PACED Oxted to Canterbury, 71 miles
- 8 day wakling holiday, RELAXED PACED Rochester to Canterbury 43 miles
Please see details and prices below.
The Pilgrims Way walking holiday connects with:
- The South Downs Way at Winchester
- The Clarendon Way at Winchester
- closely follows the route of the North Downs Way
Our self-guided walking holidays are designed with your comfort and enjoyment in mind and can be tailor-made to your own personal requirements.
The routes are clearly way-marked to provide reassurance on your hiking vacation.
We use a selection of guest houses, inns or small hotels with en-suite or private bathroom to ensure you are well rested each night after a busy day hiking and sightseeing. Rest assured that all our accommodation walking holiday providers are hand-picked and offer you that famous British hospitality.
Special diets can be catered for, including vegetarian, vegan, and gluten free.
We organize the luggage transfer so your bags are at your next accommodation when you arrive. We try to get your bags delivered by 4pm, but this may be delayed due to road conditions.
Let’s Go Walking has developed one of the largest selection of walking holidays.
Our offices are staffed 9am to 9pm during our walking season (March to September) to ensure your walking holiday runs without a hitch.
All our walking holidays are self-guided and you must be a confident map reader and able to navigate from a compass bearing. The weather in the UK and Ireland can change quickly effecting visibility and underfoot conditions. It is important to carry a selection of clothing with you on your hike each day to cope with changing weather conditions. If you are not confident of completing any days walk, do not set out.
This walking holiday in the UK operates March to September and in either direction.
The daily distances are only a suggestion. If you would like to walk longer or shorter distances, we can arrange that too.
Our stated distances include mileage to the accommodation or pickup point and so may not agree with the guide book mileages.
Rest days can be taken in any location.
Why not combine this walk with a hiking tour in another part of the UK or Ireland. Our staff will be happy to advise on necessary transfers.
Online booking available.
A deposit of £85 per person is required to secure the booking, with the balance due 6 weeks before departure.
Optional extra days and accommodation upgrades can be added during the booking process online.
Please wait for the confirmation of your holiday before making final travel plans just in case your holiday is not available for your requested date.
Winchester to Canterbury
in England UK
16 day itinerary
14 days walking and 15 nights
Suggested Itinerary
| Day 1: | arrive Winchester | |
| Optional Day: | optional extra day in Winchester | |
| Day 2: | Winchester to Alresford | 9 miles |
| Day 3: | Alresford to Alton | 10 miles |
| Day 4: | Alton to Farnham | 9 miles |
| Day 5: | Farnham to Guildford | 11 miles |
| Day 6: | Guildford to West Humble | 14 miles |
| Day 7: | West Humble to Reigate | 8 miles |
| Day 8: | Reigate to Tatsfield/Oxted | 13 miles |
| Day 9: | Tatsfield/Oxted to Dunton Green | 10 miles |
| Day 10: | Dunton Green to Vigo | 9 miles |
| Day 11: | Vigo to Rochester | 9 miles |
| Optional Day: | optional extra day in Rochester | |
| Day 12: | Rochester to Aylesford | 8 miles |
| Day 13: | Aylesford to Lenham | 13 miles |
| Day 14: | Lenham to Boughton Lees | 9 miles |
| Day 15: | Boughton Lees to Canterbury | 13 miles |
| Optional Day: | optional extra day in Canterbury | |
| Day 16: | depart Canterbury |
16 day itinerary 15 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £2,040 | £3,195 | £3,420 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Winchester to Canterbury
Suggested Tour Duration:
15 nights, 14 days walking
Total Distance:
146 miles/234 kms
Min/max daily distance:
8/14 miles
Average Daily distance:
10 miles
Grading:
Moderate
Features:
Winchester Cathedral
Jane Austin’s House
Farnham Castle
Rochester Cathedral
Aylesford Priory
Leeds Castle
Canterbury Cathedral
This route connects with:
South Downs Way
Clarendon Way
and closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Can be added when booking online
Subject to availability Supplement per person per night
Winchester
Wykeham Arms
double/twin
£69.00
Single
please ask
Winchester Hotel
£54.00
please ask
Guildford
Harbour Hotel
double/twin
£44.50
Single
see ask
Reigate
double/twin
single
Reigate Manor Hotel
£43.00
please ask
Dunton Green
Donnington Manor Hotel
double/twin
£43.00
single
please ask
Canterbury
Falstaff Hotel
double/twin
£54.00
single
please ask
Cathedral Lodge
£60.00
please ask
Winchester to Canterbury
(not visiting Rochester)
in England UK
15 day itinerary
13 days walking and 14 nights
Suggested Itinerary
| Day 1: | arrive Winchester | |
| Optional Day: | optional extra day in Winchester | |
| Day 2: | Winchester to Alresford | 9 miles |
| Day 3: | Alresford to Alton | 10 miles |
| Day 4: | Alton to Farnham | 9 miles |
| Day 5: | Farnham to Guildford | 11 miles |
| Day 6: | Guildford to West Humble | 14 miles |
| Day 7: | West Humble to Reigate | 8 miles |
| Day 8: | Reigate to Tatsfield/Oxted | 13 miles |
| Day 9: | Tatsfield/Oxted to Dunton Green | 10 miles |
| Day 10: | Dunton Green to Vigo | 9 miles |
| Day 11: | Vigo to Aylesford | 8 miles |
| Day 12: | Aylesford to Lenham | 13 miles |
| Day 13: | Lenham to Boughton Lees | 9 miles |
| Day 14: | Boughton Lees to Canterbury | 13 miles |
| Optional Day: | optional extra day in Canterbury | |
| Day 15: | depart Canterbury |
15 day itinerary 14 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £1,904 | £2,982 | £3,192 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Winchester to Canterbury
Suggested Tour Duration:
14 nights, 13 days walking
Total Distance:
137 miles/220 kms
Min/max daily distance:
8/14 miles
Average Daily distance:
11 miles
Grading:
Moderate
Features:
Winchester Cathedral
Jane Austin’s House
Farnham Castle
Aylesford Priory
Leeds Castle
Canterbury Cathedral
This route connects with:
South Downs Way
Clarendon Way
and closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Can be added when booking online
Subject to availability Supplement per person per night
Winchester
Wykeham Arms
double/twin
£69.00
Single
please ask
Winchester Hotel
£54.00
please ask
Guildford
Harbour Hotel
double/twin
£44.50
Single
see ask
Reigate
double/twin
single
Reigate Manor Hotel
£43.00
please ask
Dunton Green
Donnington Manor Hotel
double/twin
£43.00
single
please ask
Canterbury
Falstaff Hotel
double/twin
£54.00
single
please ask
Cathedral Lodge
£60.00
please ask
Winchester to Oxted
(West Section)
in England UK
9 day itinerary
7 days walking and 8 nights
Suggested Itinerary
| Day 1: | arrive Winchester | |
| Optional Day: | optional extra day in Winchester | |
| Day 2: | Winchester to Alresford | 9 miles |
| Day 3: | Alresford to Alton | 10 miles |
| Day 4: | Alton to Farnham | 9 miles |
| Day 5: | Farnham to Guildford | 11 miles |
| Day 6: | Guildford to West Humble | 14 miles |
| Day 7: | West Humble to Reigate | 8 miles |
| Day 8: | Reigate to Tatsfield/Oxted | 13 miles |
| Day 9: | depart Tatsfield/Oxted |
9 day itinerary 8 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £1,088 | £1,704 | £1,824 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Winchester to Oxted
Suggested Tour Duration:
8 nights, 7 days walking
Total Distance:
75 miles/115 kms
Min/max daily distance:
8/14 miles
Average Daily distance:
10 miles
Grading:
Moderate
Features:
Winchester Cathedral
Jane Austin’s House
Farnham Castle
This route connects with:
South Downs Way
Clarendon Way
and closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Winchester to Oxted
Can be added when booking online
Subject to availability Supplement per person per night
Winchester
Wykeham Arms
double/twin
£69.00
Single
please ask
Winchester Hotel
£54.00
please ask
Guildford
Harbour Hotel
double/twin
£44.50
Single
see ask
Reigate
double/twin
single
Reigate Manor Hotel
£43.00
please ask
Please note the Farnborough Air Show will take place in Farnborough from Monday 22nd July to Friday 26th July 2024.
This affects the availability of accommodation in Farnham and Guildford.
Therefore when booking your walking holiday on this section of the North Downs Way or the Pilgrims Way we suggest you avoid these dates.
Oxted to Canterbury
(Eastern Section)
in England UK
9 day itinerary
7 days walking and 8 nights
Suggested Itinerary
| Day 1: | arrive Oxted/Tatsfield | |
| Day 2: | Tatsfield/Oxted to Dunton Green | 10 miles |
| Day 3: | Dunton Green to Vigo | 9 miles |
| Day 4: | Vigo to Rochester | 9 miles |
| Optional Day: | optional extra day in Rochester | |
| Day 5: | Rochester to Aylesford | 8 miles |
| Day 6: | Aylesford to Lenham | 13 miles |
| Day 7: | Lenham to Boughton Lees | 9 miles |
| Day 8: | Boughton Lees to Canterbury | 13 miles |
| Optional Day: | optional extra day in Canterbury | |
| Day 9: | depart Canterbury |
9 day itinerary 8 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £1,088 | £1,704 | £1,824 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Oxted to Canterbury
Suggested Tour Duration:
8 nights, 7 days walking
Total Distance:
71 miles/120 kms
Min/max daily distance:
8/13 miles
Average Daily distance:
11 miles
Grading:
Moderate
Features:
Rochester Cathedral
Aylesford Priory
Leeds Castle
Canterbury Cathedral
This route connects with:
Pilgrims Way closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Oxted to Canterbury
Can be added when booking online
Subject to availability Supplement per person per night
Dunton Green
Donnington Manor Hotel
double/twin
£43.00
single
please ask
Canterbury
Falstaff Hotel
double/twin
£54.00
single
please ask
Cathedral Lodge
£60.00
please ask
Oxted to Canterbury
RELAXED PACE
(Eastern Section)
in England UK
11 day itinerary
9 days walking and 10 nights
Suggested Itinerary
| Day 1: | arrive Oxted/Tatsfield | |
| Day 2: | Tatsfield/Oxted to Dunton Green | 10 miles |
| Day 3: | Dunton Green to Vigo | 9 miles |
| Day 4: | Vigo to Rochester | 9 miles |
| Optional Day: | optional extra day in Rochester | |
| Day 5: | Rochester to Aylesford | 8 miles |
| Day 6: | Aylesford to Leeds Castle/Hollingbourne | 9 miles |
| Optional Day: | optional extra day in Hollingbourne to visit Leeds Castle | |
| Day 7: | Leeds Castle to Lenham | 5 miles |
| Day 8: | Lenham to Boughton Lees | 9 miles |
| Day 9: | Boughton Lees to Chilham | 6 miles |
| Day 10: | Chilham to Canterbury | 7 miles |
| Optional Day: | optional extra day in Canterbury | |
| Day 11: | depart Canterbury |
11 day itinerary 10 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £1,360 | £2,130 | £2,280 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Oxted to Canterbury
Suggested Tour Duration:
10 nights, 9 days walking
Total Distance:
71 miles/120 kms
Min/max daily distance:
5/10 miles
Average Daily distance:
8 miles
Grading:
Moderate
Features:
Rochester Cathedral
Aylesford Priory
Leeds Castle
Canterbury Cathedral
This route connects with:
Pilgrims Way closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Oxted to Canterbury
Can be added when booking online
Subject to availability Supplement per person per night
Dunton Green
Donnington Manor Hotel
double/twin
£43.00
single
please ask
Canterbury
Falstaff Hotel
double/twin
£54.00
single
please ask
Cathedral Lodge
£60.00
please ask
Rochester to Canterbury
RELAXED PACE
(Eastern Section)
in England UK
8 day itinerary
6 days walking and 7 nights
Suggested Itinerary
| Day 1: | arrive Rochester | |
| Optional Day: | optional extra day in Rochester | |
| Day 2: | Rochester to Aylesford | 8 miles |
| Day 3: | Aylesford to Leeds Castle/Hollingbourne | 9 miles |
| Optional Day: | optional extra day in Hollingbourne to visit Leeds Castle | |
| Day 4: | Leeds Castle to Lenham | 5 miles |
| Day 5: | Lenham to Boughton Lees | 9 miles |
| Day 6: | Boughton Lees to Chilham | 6 miles |
| Day 7: | Chilham to Canterbury | 7 miles |
| Optional Day: | optional extra day in Canterbury | |
| Day 8: | depart Canterbury |
8 day itinerary 7 nights
| Double or Twin Occupancy | Single Occupancy travelling with others | Solo Traveller |
|
| 2024 | £952 | £1,491 | £1,596 |
All prices subject to change
Extra nights from £64.00 per person
depending on location
Pilgrims Way Walking Holiday
Rochester to Canterbury
Suggested Tour Duration:
7 nights, 6 days walking
Total Distance:
43 miles/69 kms
Min/max daily distance:
5/9 miles
Average Daily distance:
7 miles
Grading:
Moderate
Features:
Rochester Cathedral
Aylesford Priory
Leeds Castle
Canterbury Cathedral
This route connects with:
Pilgrims Way closely follows the route of the North Downs Way
Optional Accommodation Upgrades for
Pilgrims Way Walking Holiday
Rochester to Canterbury
Can be added when booking online
Subject to availability Supplement per person per night
Canterbury
Falstaff Hotel
double/twin
£54.00
single
please ask
Cathedral Lodge
£60.00
please ask
What’s included
in your Pilgrims Way Walking Holiday in South England
- accommodation at high quality guest houses, inns or small hotels on a bed and breakfast basis
- room with en-suite or private bathroom, tea and coffee making facilities
- daily luggage transfer
- support should there be any problems on route
- detailed itineraries
- OS 1:25,000 map
- guide book to The Pilgrims Way
Optional Extras
for your Pilgrims Way Walking Holiday in South England
- upgrade to the region’s most elegant, prestigious and famous hotels, where available
- transfers back to car or station
- parking facilities
- rest days
- inn to inn walks
What’s not included
in your Pilgrims Way Walking Holiday in South England
- lunches and dinners
- travel insurance
- entrance to Leeds Castle
- entrance to local attractions
Lunches and Dinners
These are not included.
Evening meals
These are available at overnight locations, either at your accommodation or in the town/village.
Packed lunches
These can be provided by your accommodation or can be obtained from a local store, or cafe or inn along the route.
Holiday Travel Insurance
We require that you take out holiday insurance as Let’s Go Biking Ltd accepts no liability for the following:
cancellation, personal accident, illness, loss/theft of personal possessions and/or money, and any unforeseen circumstances, especially travel delays.
This is in addition to our existing
booking conditions.
Pilgrims Way Walking Holiday:
How to get there:
- By Plane to London, Gatwick, Bournemouth or Southampton where we can arrange transfer to the start of your walk
- By Car to Winchester or Oxted where parking is available
- By Train/Bus to Winchester or Oxted
This is a 146 mile walking holiday on the Pilgrims Way from Winchester to Canterbury via Rochester.
This is one of our Hampshire Walking Holidays, one of our Pilgrimage Walking Holidays, and also one of our Southern England Walking Holidays.
Please contact us if you have any questions.
Our telephone Lines are open 7 days a week.
UK +44 (0)1837 880075
or +44 (0)207 193 1252
March to September 9am to 9pm
October to February 9am to 5pm
US +1 (646) 233-1541
New York 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
AUS +61 (02) 8006 0182
Sydney 10 hours ahead of UK time:
March to September 7pm to 7am EADT
October to February 7pm to 3am EADT
CAN +1 (647) 4786251
Toronto 5 hours behind UK time:
March to September 4am to 4pm EST
October to February 4am to 12noon EST
or
Our pilgrimage walking holidays in the UK include Pilgrims Way, Clarendon Way, Saints Way, St Cuthberts Way and St Oswalds Way.
This is one of our categories of walking holidays.
