Wye Valley Walk

Wye Valley Walk

A self-guided walk along the Anglo-Welsh Border and through Wales, from Chepstow to Rhyd-y-Benwch.

3 to 14 nights
23-140 miles
Easy / Moderate to Strenuous

From £355 per person

Find your holiday

About the trail

Follow the River Wye along the Anglo-Welsh border and across to the river’s source in Mid-Wales on a walk full of contrasts, from deep limestone gorges capped with ancient woodland to the water meadows and apple orchards of Herefordshire.

Some steep, rocky sections may provide a mild challenge, but the walk keeps primarily to easy pathways through gently undulating countryside. The Wye Valley Walk is an intensely green and enjoyable venture that walkers of all interests will enjoy.

We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.

Choose your route

  • This route includes dog friendly tour options Wye Valley Walk
  • This route includes dog friendly tour options Wye Valley Walk - South Section
  • This route includes dog friendly tour options Wye Valley Walk - North Section
  • This route includes dog friendly tour options Wye Valley Short Break - Circular
  • This route includes dog friendly tour options Wye Valley Short Break - South Section

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

About this route

5 to 10 nights
77 miles
Easy / Moderate to Strenuous
2nd January to 24th December
Includes Dog-Friendly Tours

From £605 per person

Wye Valley Walk - South Section

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.

Available tours

Code Tour Duration Difficulty Price per person
WVWS1 From Chepstow to Hay-on-Wye 5 nights, 4 days walking Strenuous £605
WVWS2 From Chepstow to Hay-on-Wye 7 nights, 6 days walking Moderate / Demanding £840
WVWS3 From Chepstow to Hay-on-Wye 8 nights, 7 days walking Moderate £955
WVWS4 From Chepstow to Hay-on-Wye 10 nights, 9 days walking Easy / Moderate £1190

Short breaks

Code Tour Duration Difficulty Price per person
WVSB1 A circular trail beginning at Chepstow 3 nights, 2 days walking Demanding £355
WVSB2 A circular trail beginning at Chepstow 4 nights, 3 days walking Moderate £475
WVSB3 A circular trail beginning at Chepstow 6 nights, 5 days walking Easy / Moderate £700

Wye Valley Way - South Section 5 nights, 4 days walking

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

Important information

This tour is available to book all year, however out of season from mid October to March, there may be a small supplement for luggage moves, which will be moved by taxi rather than the usual luggage courier.


Travel to Chepstow where your first night's accommodation will be booked

Day 1

Chepstow to Monmouth. 17.5 miles (28km)

Day 2

Monmouth to Ross-on-Wye. 18.5 miles (29.5km)

Day 3

Ross-on-Wye to Hereford. 18 miles (29km)

Day 4

Hereford to Hay-on-Wye. 23 miles (37km)


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 in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

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
£60.00 per person / per night
Single Supplement
£50.00 per person / per night

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

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

What's included?

  • 5 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 border town of Monmouth is another fascinating place for a rest day, with its 13the century bridge over the River Monnow, the Norman church of St Thomas and the ruins of Monmouth Castle.

Ross-on-Wye, located on the River Wye, is a picturesque town with a range of historic buildings, including the ruins of Wilton Castle. There are also a range of shops along the quaint streets.

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.

The historic market town of Rhayader is a good choice for a rest day. Set in the beautiful Elan Valley, there are a range of local walking routes to discover along with a range of historic buildings. For wildlife lovers, a visit to the Gigrin Farm Red Kite Centre is a must. From here, you can see the majestic Red Kite come down to feed.

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: 5 nights, 4 days walking
Minimum daily distance: 17.5 miles (28 km)
Maximum daily distance: 23 miles (37 km)
Code: WVWS1 Grade: Strenuous
Season: 2nd January - 24th December
Start of holiday: Chepstow
End of holiday: Hay-on-Wye

Route Profile

Wye Valley Way - South Section Route Profile

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 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, but rather infrequently, so a taxi may be a better option.

From London

Trains run from London Paddington station to Chepstow.

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.

Customer reviews from the Wye Valley Walk - South Section

“Everyone in our group said they had a great experience hiking the Wye River Valley. All expectations for a trip filled with beautiful landscapes and quaint villages were met.”
Mr Rabert, USA
“A lovely walk and very dog friendly.”
Mrs May, UK
“As ever it was all extremely well organised. Interesting route, easy to follow instructions. Everything about it was good quality from the accommodation, taxi transfers, maps and guidebook. We would like to do a dog friendly Isle of Wight if possible!”
Mrs Donnelly, UK
“The walk as a whole was glorious.”
Mr Cartwright, UK
“Incredible countryside great accommodation. The Wye Valley way was one of the most enjoyable of all our walks. A little tough in places.”
Mr Styles, UK
“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
“Everything worked as it should have done, the walk was varied and very pleasant and the accommodation and meals were mostly good or excellent.”
Mr Welch, UK
“Enjoyed the holiday very much! Well-organized and great accommodations.”
Ms Rodger, Canada
“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
Find your holiday