Chepstow is right on the border of England and Wales and overlooks the beautiful River Wye just before it meets the Severn. The town is rather charming with a network of narrow streets lined with impressive Georgian town houses, medieval cottages and colourful terraces; there’s a distinctly romantic air with the oldest stone castle in Wales standing high on the cliffs, and the ruins of an ancient priory. It’s nice to hang out down by the river; you can take a boat trip, take in live music at the bandstand, and spot peregrine falcons nesting in the cliffs. As it’s the starting point of the Wales Coast Path, there’s an annual walking festival in the spring with guided walks taking in the gorgeous countryside and the flora and fauna. It’s famous for its racecourse where the Welsh Grand National is run, and is a good base for exploring the spectacular Wye Valley.
Good places to eat? Try the Riverside Wine Bar for British and Mediterranean cuisine, Stone Rock Pizza for what else, but pizzas, or Chepstow Castle Inn for pub food.