Wye Valley Short Break - South Section

Wye Valley Short Break - South Section

A short walking holiday from Chepstow to Symond's Yat through the Welsh Borders.

4 nights
23 miles
Easy / Moderate

From £420 per person

Discover the available tours

About this route

Crisscross the Anglo-Welsh border on woodland tracks, disused railway lines and riverside paths. This short break samples the southernmost section of the Wye Valley Walk, filled with enticing sights and varying terrain that make this a fantastic option for those looking for a shorter holiday.

The varied terrain here hosts dramatic waterfalls and historic architecture, including the New Weir Ironworks and Wyastone Leys Country House. There are a handful of climbs to deliver you to stunning viewpoints, but the trail is chiefly low-level.

© Contours Walking Holidays Wye Valley Short Break - South Section map
Chepstow to Symonds Yat
23 miles (37 km)
2nd January to 24th December

Holiday highlights

Hopping between England and Wales on a historical journey of discovery and amazing scenery.

Catching rare glimpses of fallow deer, wild boar, bats and a variety of birdlife from the various viewpoints along the trail.

Setting off from the historic town of Chepstow, home to the first stone-built Norman castle in Britain.

Available tours

CodeTourDurationDifficultyPrice per person
WVWSBS From Chepstow to Symonds Yat 4 nights, 3 days walking Easy / Moderate£420

Wye Valley Short Break - South Section 4 nights, 3 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 Tintern. 6 miles (9.5km)

Day 2

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

Day 3

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


Depart from Symonds Yat 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?

  • 4 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 an 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: 23 miles (36.5 km)
Duration: 4 nights, 3 days walking
Minimum daily distance: 6 miles (9.5 km)
Maximum daily distance: 8.5 miles (13.5 km)
Code: WVWSBS Grade: Easy / Moderate
Season: 2nd January - 24th December
Start of holiday: Chepstow
End of holiday: Symonds Yat

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, Birmingham and Rhoose-Cardiff.

By Rail - There is a rail station at the start of the trail (Chepstow). The nearest rail stations to the end of the trail (Symonds Yat) are either Lydney (about 15 miles away) or Hereford (about 17.5 miles away).

By Bus - Various bus services run to Chepstow. Unfortunately there are no bus services that run from Symonds Yat to nearby towns, so a taxi will be required.

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

Return To The Start - The easiest way to return to the start of the trail, is to take a taxi from Symonds Yat 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.

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 - 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 - 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