Offa's Dyke Path Walking Holiday | South
Chepstow, Gwent, UK 6 nights from £695

Offa's Dyke Path Walking Holiday | South

The Offa’s Dyke 8th Century ancient monument stretches the length of the Welsh-English border. Hike the south section from Sedbury cliffs and discover castles, quaint towns and medieval abbeys.

  • 5 days hiking

Highlights

Visit Chepstow Castle

Visit Chepstow Castle

See the expanse of beautifully preserved castle stretched out along limestone cliff above the River Wye.

Devil's Pulpit views

Devil's Pulpit views

Savour the scene from the limestone rock jutting out from the cliffs high above the River Wye giving you breathtaking views over Tintern Abbey.

Abergavenny market town

Abergavenny market town

Explore its castles, mansions, Roman remains and standing stones as well as its shops, cafes and pubs.

History, interest, learning

History, interest, learning

Follow a route jam-packed with features and learn from your accompanying guide.

Black Mountains ridge

Black Mountains ridge

Keep an eye out for herds of wild ponies, birds of prey, paragliders and parachutes!

Overview

Hike the southern section of Offa's Dyke Path, from Sedbury Cliffs to Haye-on-Wye.

The Offa’s Dyke 8th Century ancient monument stretches the length of the Welsh-English border. Spanning 285km (177 miles) from Chepstow to Prestatyn, this National Trail crosses three Areas of Outstanding Natural Beauty. Discover castles, quaint towns and medieval abbeys as you walk the Southern section of Britain’s longest ancient monument from Sedbury Cliffs to Hay-On-Wye.

Named after King Offa, the dyke was ordered to be constructed to divide his kingdom of Mercia from rival kingdoms in what is now Wales.

Take in beautiful views of the Black Mountains in the Brecon Beacons National Park, as well as charming villages, including Hay-on-Wye with its world-famous bookshops.

This section of Offa’s Dyke Path crosses a variety of terrain, including quiet semi-ancient woodland and rolling hills, with plenty of fascinating folklore to discover, such as the mysterious limestone pillar of the Devil’s Pulpit.

Need to know

  • South Wales

    Beautiful views over the Black Mountains in the Brecon Beacons National Park.

  • Adventure specialists

    Designed for people who want fresh challenges in new territories and led by professional, local English-speaking guides.

  • Carefully-curated route

    Castles, quaint towns, medieval abbeys and fascinating folklore such as the mysterious limestone pillar of the Devil’s Pulpit.

Dates

  • Flexible, bespoke, group bookings - Find out more today

  • Mountain
  • Forest
  • Average fitness
  • Solo
  • Groups
  • Couples

Accommodation

6 nights' accommodation in carefully selected hotels, inns and guest houses including:

  • Boutique family-run guest house in the heart of Chepstow 
  • Countryside inn nestled in the town of Tintern 
  • Hotel, originally an 18th century coaching inn 
  • Small family-run hotel in the historic market town of Abergavenny 
  • Hotel in Hay-on-Wye

 

Single room supplement

If you would prefer your own room this can usually be accommodated, though an extra charge would apply.

Twin rooms

Solo explorers will be matched up with a likeminded traveller to share with as the rooms are on a twin basis.

Locally-sourced food

Accommodation and catering partners have been carefully selected based on their commitment to sourcing local produce, organically produced wherever possible.

Kit list

  • Comfortable waterproof walking boots or shoes
  • Walking socks
  • Waterproof jacket & trousers
  • Walking poles (optional)
  • Warm layers for walking
  • Warm hat and gloves
  • Suncream
  • Head torch
  • Small first aid & blister kit
  • Day backpack – to carry hydration, lunch, snacks and spare clothing

 

Season

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

  • Bag transfer
  • Transfers

Meeting point

Chepstow
Chepstow
Chepstow
Gwent
NP16
UK

Getting there

  • By air

    The closest international airport to the tour start point in Chepstow is Bristol Airport. It is approximately a 1 hour taxi transfer from the airport to the tour start point in Chepstow or alternatively travel by rail to Chepstow. The closest international airports to the tour endpoint in Hay-On-Wye are Birmingham Airport and Bristol Airport. It is approximately a 2.5 hour taxi transfer to either airport from the tour end point in Hay- On-Wye or alternatively take a taxi transfer to the nearest railway station in Hereford.

  • By rail

    The closest train station to the tour start point in Chepstow is Chepstow Station. From Chepstow Station, it is a 10 minute walk to your accommodation. From the tour end point in Hay-on-Wye, the closest train station is Hereford Station. Hereford Station is a 40 minute drive from your accommodation.

  • By road

    Chepstow is located less than 30 minutes from the A5, and less than 1.5 hours from the M56 and less than 3 hours from the M54 motorways. Hay-On-Wye is located less than 1.5 hours from the M54 and M6 motorways.

  • Hill
  • Mountain
  • Forest
  • Minibus

Itinerary

  • Day 1 | Arrival and welcome

    Check into your boutique family-run guest house in the heart of Chepstow.

    This afternoon, why not visit Chepstow castle, the oldest surviving castle in Wales dating from 1067? Or perhaps take a stroll through this medieval town. Chepstow, which means marketplace in Old English, is a great place for a little shopping. You’ll find plenty of tempting independent boutiques amid the handsome Georgian and Victorian buildings in the centre of town.

    Following a welcome meeting with your Tour Leader, get to know your fellow travellers over dinner this evening, ahead of your epic journey together along the Welsh-English border.

CHEPSTOW CASTLE
Stretching out along a limestone cliff above the River Wye and beautifully preserved.
  • Day 2 | Sedbury Cliffs to Tintern (13km)

    Enjoy a hearty breakfast ahead of the first day of your journey. Today your group will cover around 12km, taking you through a semi-ancient wooded valley and along picturesque rivers with some incredible viewpoints, including the Devil’s Pulpit. The Devil’s Pulpit is a viewpoint and limestone rock jutting out from the cliffs high above the River Wye offering breathtaking views over Tintern Abbey.

    Drop down to visit the picturesque village of Tintern, which hugs the Wye at this point and take time to visit Tintern Abbey, founded in 1131 by monks of the Cistercian Order. Tintern Abbey is a national icon, standing on the banks of the River Wye for nearly 500 years.

    Arrive at your countryside inn nestled in the town of Tintern and enjoy your free evening.

DEVIL'S PULPIT
Savour the view from the limestone rock jutting out from the cliffs high above the River Wye giving you breathtaking views over Tintern Abbey.
  • Day 3 | Tintern to Monmouth (18km)

    After breakfast, follow the River Wye as you leave Tintern behind and set off on the next stretch of Offa’s Dyke Path.

    Enjoy the relatively flat first half of today’s walk as you follow the River Wye’s edge, before climbing steadily up through the beautiful semi-ancient woodland of the Wye Valley Area of Outstanding Natural Beauty. As you near the outskirts of Monmouth town, pause to explore The Kymin, a charming 18th-century Round House and Naval Temple. Make sure you pay a visit to Monmouth Castle and Monnow Bridge, Great Britain’s only remaining fortified river bridge, in the centre of town before you head to your hotel for the night.

    Check into your accommodation for this evening, originally an 18th century coaching inn. Monmouth has officially been named as the UK’s first Bee Town, thanks to the local council’s work to make the town a better place for pollinators. Why not visit the Bees for Development shop in town, selling handmade gifts to support beekeepers in the poorest communities.

MONNOW BRIDGE
Great Britain’s only remaining fortified river bridge.
  • Day 4 | Monmouth to Llangattock Lingoed (23km)

    Today’s stretch of Offa’s Dyke Path is around 23 kilometres, leaving Monmouth behind and heading to the small village of Llangattock Lingoed. As you walk through the open countryside, you may be able to spot The Kymin behind you.

    Take in the incredible landscape as you climb through King’s Wood, across open farmland and along the River Trothy. Offa’s Dyke Path leads you past the medieval Llanvihangel-Ystern-Llewern church, a 15th century active parish. Back in the open landscape, you might see the mountains of Skirrid and Sugar Loaf visible in the distance.

    Upon arrival at the tiny village of Llangattock Lingoed, you’ll be collected from Offa’s Dyke Path and taken to the small family-run hotel in the historic market town of Abergavenny, where you’ll be based for the next two nights. This small market town has history and heritage in spades, from castles and mansions to Roman remains and standing stones.

ABERGAVENNY
Castles, mansions, Roman remains and standing stones.
  • Day 5 | Llangattock Lingoed to Longtown (14km)

    A short transfer will bring you back to Offa’s Dyke Path. Walk through rolling fields and farmland today as you leave Llangattock Lingoed behind. As you pass the pretty white pre-Norman church of St Cadoc on the edge of the village, take a moment to head inside and view the impressive early 15th century wall painting.

    Later today you’ll cross the highest point along the southern section of Offa’s Dyke Path at Hatterall Ridge as you walk through the stunning Black Mountains.

    On arrival at Longtown, you'll be collected from Offa’s Dyke Path and return to Abergavenny for your second night. After finishing a shorter day of walking, why not head into town this afternoon and explore Abergavenny’s history?

  • Day 6 | Longtown to Hay-on-Wye (21km)

    After a tasty breakfast, you’ll be returned to Offa’s Dyke Path. Pass by the ruins of Longtown’s 12th century Norman castle as you continue your journey. Climb back up on top of the ridge of the Black Mountains in Brecon Beacons National Park and keep an eye out for herds of wild ponies, birds of prey and views to the Vale of Ewyas. This is also a popular paragliding spot so keep your eyes peeled for brightly-coloured parachutes filling the sky above!

    Just before reaching Hay Bluff, make a final descent into Hay-on-Wye, world-renowned for its books and bookshops. 

    Spend your last evening celebrating your awesome achievement relaxing at your hotel. Or perhaps head into the bustling market town for a few well-earned Welsh beers.

  • Day 7 | Depart

    It’s time to pack your things and say goodbye to your fellow walkers as you enjoy your final breakfast. Expect to leave the hotel at 10:00.

  • Accommodation
  • Guides
  • Meals
  • Transfers

Included

  • 6 nights' accommodation
  • 5 full days of guided walking
  • Breakfast daily
  • Welcome evening meal
  • Daily luggage transfers
  • 4 transfers to and from accommodation
  • Professional, local, English-speaking guide
  • 1 native tree planted in the woodland

  • Carbon offset
  • Plastic bottle free

Caring for the world as you do

This adventure supports local, independent businesses. Local guides are always used – people who will give you a more authentic experience and share the hidden secrets only local adventurers can bring. And because this is their home, they have a truly active interest in caring for their environment.

The carbon footprint of all trips is measured and reduced to be as low as possible. Any carbon that is yet to be mitigated is off-set through a local tree planting project. One tree exceeds what is needed to offset the emissions of your low carbon adventure holiday.

Here is a summary of the Sustainability Policy:

Economic responsibility

  • Keeping it local

    Working exclusively with local, independently-owned businesses to ensure your money goes straight into the communities that you're visiting.

  • Fair pay for quality service

    Treating partners fairly for the high standards of service they deliver to you, whilst still ensuring value for money.

  • Supporting local producers

    Local, independent shops, accommodation, bars and eateries are used and encouraged.

Environmental responsibility

  • Low carbon travel

    Ensuring the carbon footprint of this adventure is offset by planting native broadleaf trees, including oak, ash and birch.

    Responsibility is taken for ensuring the carbon footprint of your travel is offset. By working with the Clwydian Range and Dee Valley AONB, the unavoidable carbon emissions created by travel are offset, but also new, biodiverse woodland areas within the UK are created that will benefit both the planet and the community. Planting native broadleaf trees, including oak, ash and birch, is helping to increase the available natural habitat for the UK’s native wildlife. Species such as bullfinches, beavers, the brimstone butterfly and many more are all benefitting from this.

  • Avoiding single-use plastics

    Reusable aluminium bottles are provided on arrival at your accommodation and packed lunches use more sustainable wrapping such as paper bags or wax paper wrap.

  • Locally sourced food

    Accommodation and catering partners have been carefully selected based on their commitment to sourcing local produce, organically produced wherever possible.

  • Blue Flag Award

    Partnering with one of the first boat tour operators in the UK to be awarded the prestigious Blue Flag Sustainable Boat Tour Operator status.

Social responsibility

  • Small group tours

    The primary concern with tourism in the UK’s wild spaces is to ensure it only has a positive impact on the local communities and culture so for this reason small group trips never exceed 15 guests.

  • Live like a local

    Learning the history and culture of a region plays a big role in your travelling experience – it’s what brings a place to life.

  • Read the landscape

    The historical significance of the area is brought to life by the local guides who help you understand the features of the landscape.

  • Learn the language

    Keeping local languages alive is sacred, so you’re encouraged to learn simple words and phrases during your time on the adventure.

  • Understanding farming culture

    Respecting the countryside code and understanding farming practices are important for visitors to the area.

Adventure promise

Making travel better for everyone

The Adventure Promise is simple and honest. It’s the commitment that this challenge will always do right by you, local communities and the world we live in:

  • Payment Instalments
  • Flexible Booking
  • Low Carbon
  • Low Impact
  • Support Local
  • All Abilities
  • Covid Secure

 

Costs

Price per person (inc deposit)

£695.00

Enquiries & bookings

If you have any questions or would like to check availability or make a booking, please provide a few details about you, your group size and any preferred dates. A member of the team will then get back to you or you can go ahead and book online.