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

3 to 6 nights
36 miles
Easy / Moderate to Demanding
2nd January to 24th December
Includes Dog-Friendly Tours

From £355 per person

Wye Valley Short Break - Circular

Explore both banks of the Wye between Chepstow and Monmouth on this low mileage tour. The trail features spectacular viewpoints to admire nature flourishing on the river at Wintours Leap, the Devil’s Pulpit, Eagle’s Nest and Kymin Hill.

Human history is well-represented too, with several castles to visit, a unique medieval gateway leading the way into Monmouth, and the romantic ruin of Tintern Abbey awaiting a visit. This is a truly verdant space; this ancient woodland contains the finest selection of native British trees to be found anywhere in the wild.

 

Available tours

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

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 Short Break - Circular 3 nights, 2 days walking

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

Important information

This is a circular tour, travelling north from Chepstow to Monmouth via Offa's Dyke Path and returning south along the Wye Valley Walk. On some itineraries, this shows as "Redbrook-on-Wye to Redbrook-on-Wye" - indicating a walk north to Monmouth and back again.

 

Start

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

Day 1

Chepstow to Monmouth. 18 miles (28.5km)

Day 2

Monmouth to Chepstow. 17.5 miles (28km)

Finish

Depart from Chepstow 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
Standard
Interactive
© Contours Walking Holidays Wye Valley Short Break - Circular map
Circular trail beginning at Chepstow
36 miles (57 km)
2nd January to 24th December

Holiday highlights

Visiting the fascinating castles at Monmouth and Chepstow.

Admiring the view from Wintour’s Leap and spotting Peregrine Falcons on the cliff tops.

Enjoying beautiful riverside walking in ancient woodlands.

What's included?

  • 3 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 or simply resting your legs, an extra day can give you more time to cherish your surroundings.

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

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.

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

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

Tour Facts

Total distance: 35.5 miles (56.5 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 17.5 miles (28 km)
Maximum daily distance: 18 miles (28.5 km)
Code: WVSB1 Grade: Demanding
Season: 2nd January - 24th December
Start of holiday: Chepstow
End of holiday: Chepstow

Route Profile

Wye Valley Short Break - Circular 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 Chepstow.

By Bus - Various bus services run to and from Chepstow.

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

Return To The Start - The Wye Valley Short Break is a circular tour beginning and ending in 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.
"Chepstow Castle" by Jane Wilde (2020) "Chepstow Castle" by Jane Wilde (2020)
"View from Devil's Cave" by Jane Wilde (2020) "View from Devil's Cave" by Jane Wilde (2020)
"Approaching Redbrook-on-Wye" by Jane Wilde (2020) "Approaching Redbrook-on-Wye" by Jane Wilde (2020)
"Wintour's Leap" by Jane Wilde (2020) "Wintour's Leap" by Jane Wilde (2020)
"Chepstow" by Jane Wilde (2020) "Chepstow" by Jane Wilde (2020)

Customer reviews from the Wye Valley Short Break - Circular

“We have just completed our walk - another great success... We found you very prompt with your email responses to our queries so well done and thanks again. All in all though, another great holiday and we will certainly book with you again in the future.”
Dr Fontaine, Australia
“Both your directions booklet, map and the taxi service all worked very well and were much appreciated.”
Ms Bown, UK
“Beautiful scenery and interesting historic towns.”
Mrs Andrews, UK
“The accommodation was good. The walk was the right distance for us each day. Overall it was a great holiday and we both really enjoyed it and would certainly book with you again. It was glitch free and the accommodation was very good. We have already sent your website to friends with high recommendations.”
Ms Crimeen, UK
“The route was well marked and each day we walked a section that was manageable. We were fortunate that each day was dry, the paths in some places were wet from overnight rain and slippery. A spectacular walk.”
Ms Burlton, UK
“Very nice walk, walking guide good, all paths well waymarked. We were a party ,all in our seventies, and we all enjoyed the walk though it might be difficult in the wet.”
Mr Hughes, UK
“The route was excellent and daily mileage spot on.”
Mr Roberts, UK
“The Offa’s Dyke Ppath is clearly marked and can be hard in parts, but it was an enjoyable walk. The walk went well and communication leading up to the holiday was good. I would have no hesitation booking another holiday.”
Ms Buhler, UK
“This was a perfect short break for Springtime. The walking was varied and satisfying and the accommodation very welcoming and comfortable.”
Ms Simmonds, UK
Find your holiday