Chepstow

Roman ruins peek through bracken on the hills above town, where ancient burial chambers like Gaer-Ilwyd Dolmen remind you this border country has seen empires rise and fall. Chepstow sits where the River Wye sweeps towards the Severn, its medieval castle commanding the crossing point between England and Wales for nearly a thousand years.

The old town feels properly Welsh despite being technically in England - narrow streets wind past The Procurator's House, a beautifully preserved medieval merchant's dwelling that now houses Chepstow Museum. Market day brings farmers down from the hills, and the pubs fill with a proper mix of locals and walkers fresh off the Wye Valley footpaths.

Woodland covers the surrounding hills like a green blanket. Chepstow Park Wood and New Wood offer decent walking, while the more adventurous can tackle Gaer Hill or Mount St Albans for cracking views across the valley. Ravensnest Wood lives up to its name - atmospheric stuff, especially when mist rolls off the river.

The Giant's Cave makes for an interesting scramble if you don't mind a bit of a trek through the trees. Local legend claims it's where a giant once lived, though the views suggest any self-respecting giant would have chosen well.

Caldicot station connects you to the main Cardiff-Gloucester line, making day trips dead easy. But honestly, once you're here, the pull of the Wye Valley keeps most people exploring locally.

Staying at one of the nearby parks puts you right in walking distance of both town and countryside. Forest and Wye Valley Caravan and Camping Site or Whitemead Forest Park give you that proper outdoors feeling while keeping civilization close enough for a decent pint when the weather turns.