Wye Valley Walk - South Section

Wye Valley Walk - South Section

From Chepstow to Hay-on-Wye along the Welsh Borders and through Herefordshire.

7 to 10 nights
77 miles
Easy / Moderate to Moderate / Demanding

From £725 per person

Discover the available tours

About this route

Picturesque riverside scenery surrounds you on this winding walk through the meadows of Herefordshire and the border woodlands.

This leg of the Wye Valley Walk hosts Chepstow Castle, presiding on the cliffs high over the river, and the romantic ruin of Tintern Abbey, not the mention plenty of border towns steeped in history. Hay-on-Wye is even known as the ‘town of books’ as it’s the home of over thirty second-hand and antiquarian bookshops!

This is a wonderfully lively walking holiday with plenty of things to see and do between dreamy stints walking on the riverbank.

© Contours Walking Holidays Wye Valley Walk - South Section map
Chepstow to Hay-on-Wye
77 miles (124 km)
2nd January to 24th December

Holiday highlights

Exploring an Area of Outstanding Natural Beauty at Fownhope.

Enjoying the tranquil riverside scenery as you follow one of Britain’s longest rivers from Chepstow to Hay-on-Wye.

Visiting a series of historic attractions, including the castles at Chepstow and Goodrich and the romantic Tintern Abbey.

Available tours

CodeTourDurationDifficultyPrice per person
WVWS1 From Chepstow to Hay-on-Wye 7 nights, 6 days walking Moderate / Demanding£725
WVWS2 From Chepstow to Hay-on-Wye 8 nights, 7 days walking Moderate£825
WVWS3 From Chepstow to Hay-on-Wye 10 nights, 9 days walking Easy / Moderate£1030

Wye Valley Walk - South Section 7 nights, 6 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Travel info
  • Weather

Travel to Chepstow where your first night's accommodation has been booked

Day 1

Chepstow to Redbrook-on-Wye(L). 14.5 miles (23km)

Day 2

Redbrook-on-Wye(L) to Symonds Yat. 8.5 miles (13.5km)

Day 3

Symonds Yat to Ross-on-Wye. 13 miles (21km)

Day 4

Ross-on-Wye to Fownhope. 11 miles (18km)

Day 5

Fownhope to Monnington-on-Wye/Byford. 18.5 miles (29.5km)

Day 6

Monnington-on-Wye/Byford to Hay-on-Wye. 11.5 miles (18.5km)


Depart from Hay-on-Wye after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation; should your accommodation be further than this, transfers will be provided as standard.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£50.00 per person / per night
Single Supplement
£40.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

What's included?

  • 7 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

Taking an extra night can be the perfect way to extend your holiday. Whether you spend your time exploring the area, visiting its attractions of simply resting your legs, an extra day can give you more time to cherish your surroundings.

Chepstow, with its wealth of historic buildings including Chepstow Castle, the Gate and Port Wall, Priory Church of St Mary, is another interesting location to spend a rest day.

The sleepy town of Hay-on-Wye is a good choice for a rest day, particularly if you are keen on books. There are over 30 book stores in houses, shops, the old cinema and the ramshackle stone castle.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

Tour Facts

Total distance: 77 miles (123.5 km)
Duration: 7 nights, 6 days walking
Minimum daily distance: 8.5 miles (13.5 km)
Maximum daily distance: 18.5 miles (29.5 km)
Code: WVWS1 Grade: Moderate / Demanding
Season: 2nd January - 24th December
Start of holiday: Chepstow
End of holiday: Hay-on-Wye

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Bristol and Rhoose-Cardiff.

By Rail - There is a rail station at the start of the trail (Chepstow). The nearest rail station to the end of the trail (Hay-on-Wye) is at Hereford (about 21 miles away).

By Bus - Various bus services run to Chepstow. Buses run to from Hay-on-Wye to Hereford Monday to Saturday only, so a taxi will be required on a Sunday.

From London - Trains run from London Paddington station to Chepstow.

Return to Start - The easiest way to return to the start of the trail, is to take a taxi from Hay-on-Wye to Chepstow, as public transport options are rather lengthly.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.

Routes on this trail

Wye Valley Walk
11 to 14 nights
140 miles
Dog friendly
From £1,135 per person
A wonderful walk from Chepstow to Rhyd-y-Benwich along the Anglo-Welsh Border and through Wales.Find Out More
Wye Valley Walk - North Section
6 to 7 nights
63 miles
Dog friendly
From £620 per person
An enticing walk from Hay-on-Wye to Rhyd-y-Benwch through the wild Cambrian Mountains.Find Out More
Wye Valley Short Break - Circular
3 to 6 nights
36 miles
Easy / Moderate+
Dog friendly
From £310 per person
A short circular walking holiday along the River Wye via Chepstow and Monmouth.Find Out More
Wye Valley Short Break - South Section
4 nights
23 miles
Easy / Moderate
Dog friendly
From £420 per person
A short walking holiday from Chepstow to Symond's Yat through the Welsh Borders.Find Out More

Customer reviews from the Wye Valley Walk - South Section

“Accommodations were fabulous! Mileage was perfect. Transfers of luggage and taxis for us went without a problem.”
Mrs Mercer, USA
“Just a note of thanks to all of you at Contours that worked together to organise our 2 splendid walking trips! They were wonderfully organised and thoughtfully planned so that our trip was a memorable adventure! We loved every step of the way! Thank you so much!”
Mr Stratton, USA
“The accommodation and information package (maps and itinerary information regarding the accommodation was excellent).”
Mr Winter, UK
“Enjoyed the holiday very much! Well-organized and great accommodations.”
Ms Rodger, Canada
“Thank you for another superb holiday! We all had a really great time. It was very well organised AS ALWAYS x”
Mrs Dean, UK
“The walk and accommodation was generally excellent. A beautiful walk, challenging at times. The quality of accommodation in particular seems to have improved since my first walk with you nine years ago.”
Mr Fennell, UK
“We would like to let you know that we enjoyed our 6 days Wye Valley Walk from Hay on Wye to Chepstow last week”
Mr Lacroix, Canada
“The walk as a whole was glorious.”
Mr Cartwright, UK
“A lovely walk and very dog friendly.”
Mrs May, UK