Ruined hilltop fortifications overlooking the Welsh Marches on the Offa’s Dyke Path walking holiday

ODP-CAS1

Chepstow to Hay on Wye (castles)

Itinerary Information

Difficulty
Moderate to Challenging
Distance
49.5 miles
Walking
5 Days
Bed & Breakfast
6 Nights
Grade
Classic
Dog Friendly
No

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From £780 per person
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Itinerary Details

By combining sections of the Offa’s Dyke Path with the iconic Three Castles Trail, we’ve crafted a 5-day adventure filled with spectacular walking and a rich sense of ancient history.

Day 1Arrival Day
  1. AccommodationChepstow
Day 26 miles (9.7 km)
  1. Chepstow to Tintern

  2. AccommodationTintern
Day 311.5 miles (18.5 km)
  1. Tintern to Monmouth

  2. AccommodationMonmouth
Day 411.5 miles (18.5 km)
  1. Monmouth to White Castle

  2. transfer
  3. AccommodationLlangattock Lingoed
Day 511.5 miles (18.5 km)
  1. transfer
  2. Caggle Street to Skenfrith Castle via Grosmont

  3. transfer
  4. AccommodationLlangattock Lingoed
Day 69 miles (14.5 km)
  1. Llangattock Lingoed to Llanthony Priory
    Includes 1.7 miles to Priory

  2. transfer
  3. AccommodationHay on Wye
Day 7Departure Day

    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, hotels and B&Bs with en-suite or private facilities
    • Breakfast each morning
    • Luggage transfers between accommodation
    • 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

    Pricing From

    Jan 1, 2026Dec 31, 2026

    £780

    Per Person (Based on 2 people sharing)

    £1206 Solo Traveller

    £1038 Single Occupancy

    Rest Days

    £150 Per room per day