Wye Valley Short Break - Circular

Wye Valley Short Break - Circular

A short circular walking holiday along the River Wye via Chepstow and Monmouth.

3 to 6 nights
36 miles
Easy / Moderate to Demanding

From £310 per person

Discover the available tours

About this route

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.


© 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.

Available tours

CodeTourDurationDifficultyPrice per person
WVSB1 A circular trail beginning at Chepstow 3 nights, 2 days walking Demanding£310
WVSB2 A circular trail beginning at Chepstow 4 nights, 3 days walking Moderate£415
WVSB3 A circular trail beginning at Chepstow 6 nights, 5 days walking Easy / Moderate£620

Wye Valley Short Break - Circular 3 nights, 2 days walking

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

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.


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

Day 1

Chepstow to Monmouth. 18 miles (28.5km)

Day 2

Monmouth to Chepstow. 17.5 miles (28km)


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; 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?

  • 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

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 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.

Routes on this trail

Wye Valley Walk
11 to 14 nights
140 miles
Dog friendly
From £1,135 per person
Chepstow to Rhyd-y-Benwich along the Anglo-Welsh Border and through Wales.Find Out More
Wye Valley Walk - South Section
7 to 10 nights
77 miles
Easy / Moderate+
Dog friendly
From £725 per person
From Chepstow to Hay-on-Wye along the Welsh Borders and through Herefordshire.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 - 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 Short Break - Circular

“Fantastic mini break. Our first family walking holiday which has definitely whetted our appetite for more. Excellent pre holiday information from Contours, a brilliant route and flawless logistics throughout.”
Mr Rankin, UK
“It was delightful. The area was stunning, we especially liked the mixed woodland full of lovely birdsong.”
Ms Reinsch, UK
“Beautiful scenery and interesting historic towns.”
Mrs Andrews, UK
“Varied landscape was a big plus.”
Mr Hazlehurst, 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
“Thank you for your organisation - everything went smoothly.”
Mrs Warner, 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
“Excellent accommodation. Enjoyable walks.”
Mr Cruse, UK
“Excellent holiday.”
Mrs O’Connor, UK
"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)