View of the Wye valley from Eagle's Nest point

WVW-GIL1

Ross on Wye to Chepstow

Difficulty
Moderate
Distance
39.9 miles
Walking
3 Days
Bed & Breakfast
4 Nights
Grade
Classic
From £545 per person
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Itinerary Details

Day 1Arrival Day

Arrival and overnight at your accommodation in Ross-on-Wye.

  1. AccommodationRoss on Wye
Day 215.6 miles (25.1 km)

Ahead of you, you have a day of delightful riverside walking following the Wye as it meanders through the upper Wye gorge as well as more challenging sections with some steep climbs leading out of Ross-on-Wye and past Kerne Bridge through woodland and field. After making the ascent up Chase Hill to leave Ross, the route snakes its way around hills, meadows and trees with some challenging climbs en-route. From Kerne Bridge, there is a sudden change of pace, as your route begins to steer a close course to the river, taking you along the riverbank past Welsh Bicknor to Symonds Yat.

  1. Ross on Wye to Symonds Yat

  2. AccommodationSymonds Yat
Day 313.8 miles (22.2 km)

Today’s route takes you over the border and back again several times, as you follow the Wye’s course between Wales and England. You’ll pass the Seven Sisters Rocks, a Victorian limestone quarry that lies on one side of the track while you have the river running alongside you on the other.

  1. Symonds Yat to Llandogo

  2. transfer
  3. AccommodationTintern
Day 410.5 miles (16.9 km)

The last day of your walk features some of the Wye Valley’s more challenging sections as the route undulates quite steeply up and back down around the valley. However, these steep climbs are rewarded with some of the most distinctive and unforgettable viewpoints found in this part of the world, as you stop to take pause and appreciate the panorama over the river valley. The 12th century Tintern Abbey cuts an impressive figure in the distance on the approach to the village, where you then join a woodland trail out of the village passing beneath the Black Cliffs and re-joining the river at Lover’s Leap to follow the route into Chepstow town.

  1. transfer
  2. Llandogo to Chepstow

  3. AccommodationChepstow
Day 5

Departure from Chepstow following breakfast.

    Overnight locations and transfer arrangements may differ slightly from those shown, depending on availability.

    What's Included

    • Good standard accommodation at a mixture of guesthouses, farmhouses, local inns and B&Bs with en-suite or private facilities wherever possible
    • Breakfast
    • Luggage transfers
    • Personal transfer between accommodation and path that form a part of our standard package
    • Route planning
    • Walk pack including Trail Guide and mapping, itinerary, accommodation directions and route notes, lunch and dinner information, restaurant recommendations and holiday planning details

    Extras

    Rest days/additional nights: Prices from £75 per person per night.

    Upgrade options: Speak to our team to discuss upgrade options for this itinerary.

    Walk Pack postage: Europe - to first night’s accommodation, Rest of World - £30 supplement, (UK is included in price).

    Extra Walk Packs: can be requested, please see here for full details and supplements.

    Bank Holidays and short notice bookings may incur extra charges.

    Pricing

    Jan 1, 2026Dec 31, 2026

    £545

    Per Person (Based on 2 people sharing)

    £865 Solo Traveller

    £725 Single Occupancy

    £75 Rest Days (Per person per day)