Wye Valley Short Break - Circular

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

3 to 6 nights
35 miles
Easy / Moderate to Demanding

From £265 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
35 miles (55 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£265
WVSB2 A circular trail beginning at Chepstow 4 nights, 3 days walking Moderate£350
WVSB3 A circular trail beginning at Chepstow 6 nights, 5 days walking Easy / Moderate£525

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. 17 miles (27.5km)

Day 2

Monmouth to Chepstow. 17 miles (27km)


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.

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 walk 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 walking on your own, or are part of a group but require a room of your own, then the Solo Walker or Single Supplements apply respectively:

A note about transfers
Solo Walker Supplement
£35.00 per person / per night
Single Supplement
£25.00 per person / per night

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

Extra night (Standard)
£60.00 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)
£60.00 per person / per night

Tour Facts

Total distance: 34.5 miles (55 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 17 miles (27 km)
Maximum daily distance: 17 miles (27.5 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

11 to 14 nights
137 miles
Dog friendly
From £960 per person
A wonderful walk from Chepstow to Rhyd-y-Benwich along the Anglo-Welsh Border and through Wales.Find Out More
7 to 10 nights
75 miles
Easy / Moderate+
Dog friendly
From £610 per person
From Chepstow to Hay-on-Wye along the Welsh Borders and through Herefordshire.Find Out More
6 to 7 nights
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From £525 per person
An enticing walk from Hay-on-Wye to Rhyd-y-Benwch through the wild Cambrian Mountains.Find Out More
4 nights
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From £355 per person
A short walking holiday from Chepstow to Symond's Yat through the Welsh Borders.Find Out More

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