Sintra – Cascais

Few walking holidays offer such a change of scenery in the course of a week. In Sintra, paths climb through wooded hills to hilltop palaces, with time to wander through historic gardens and explore the old town. Further west, the landscape opens onto the Atlantic, with rocky headlands, sandy beaches and far-reaching coastal views.

The appeal lies in the contrast, and the opportunity to explore both settings properly. The first days combine shorter walks with visits to Sintra's remarkable buildings and estates. Later, longer coastal stages take you through pine woodland, traditional villages and along clifftop paths above the ocean.

There are some steep climbs and uneven coastal sections, but shorter alternatives on several days allow you to adjust the walking to suit your pace. You finish in Cascais, having experienced Portugal's royal heritage, wooded countryside and Atlantic coastline on foot.

Sintra's wooded hills have attracted Portuguese royalty and wealthy families for centuries. Their palaces and estates form a remarkable collection of architecture and landscaped gardens, recognised by UNESCO as part of Sintra's Cultural Landscape.

At Palácio da Pena, King Ferdinand II transformed an earlier monastery into a colourful 19th-century palace surrounded by gardens. The Moorish Castle, with its much older stone walls following the hilltop, provides a striking contrast.

Elsewhere, Quinta da Regaleira has underground passages and an elaborate Initiation Well, while Monserrate combines Romantic architecture with gardens planted with species from around the world.

Perhaps the greatest contrast comes at the Convento dos Capuchos, where Franciscan friars lived in small, cork-lined cells built around natural granite formations.

These places reveal different chapters of Sintra's history, from medieval fortifications and royal ambition to religious simplicity. The surrounding hills remain central to their character.