5-Day / 4-Night Moderate

From your point of arrival, use the public transport information we provide to make your way to charming Cascais. Consider taking the scenic train ride along the Estoril coast from Lisbon. Cascais is a former royal summer retreat where elegant 19th-century architecture, a lively old town and a series of beautiful beaches combine to create one of Portugal’s most appealing coastal towns. Cascais makes a wonderful starting base for the days ahead, with excellent restaurants, a picturesque harbour and the wild Atlantic coastline of the natural park waiting just beyond the town’s western edge.

Today is all about the coast and the sea. The walk begins by threading through the low ridges and valleys where the Sintra foothills run down to Cabo da Roca, the most westerly point of mainland Europe. From there, waymarked trails follow the clifftops south, with sweeping views of rocky headlands, hidden beaches, and dramatic sea stacks rising from the Atlantic. The route dips inland briefly before returning to the coast at the Fojo dos Morcegos, a spectacular sinkhole that plunges from the clifftop directly to the sea below. A well-earned stop at the beautiful Praia da Adraga – one of Portugal’s finest beaches – offers the chance for a coffee or a swim before the final stretch along the clifftops to Praia Grande, where 125-million-year-old dinosaur footprints are embedded in the near-vertical cliff face at the southern end of the beach.

From charming Colares, renowned for its unique Atlantic-grown wines, you hike uphill through pleasant woodland to the Convento dos Capuchos – a 16th-century Franciscan hermitage carved into the living rock, its tiny cork-lined cells and hidden chapels offering one of the most atmospheric and intimate religious sites in Portugal.

The walk then explores the ancient forests of the Serra de Sintra, winding through the old Monserrate Hunting Grounds, where natural springs and water mines hidden in the hillside have fed the gardens below for centuries. The route descends through this quietly beautiful landscape to the Park and Palace of Monserrate – a Victorian masterpiece of neo-Gothic, Moorish and Indian architecture set within 50 hectares of botanical gardens, ornamental lakes, and cascading waterways.

After exploring the palace and gardens, you briefly follow the Colares Stream through the valley before climbing along an ancient path up to Sintra – the magical hilltop town of palaces, royal retreats, and romantic follies that has drawn poets, kings, and travellers for centuries.

For many walkers, this is the highlight of the entire holiday. The day begins with the ascent from Sintra’s historic centre via the romantic Vila Sassetti trail, climbing through terraced gardens and woodland to the gates of Pena Park. The first stop is Pena Palace itself – perched dramatically on a rocky crag, its vivid towers and battlements rising above the treetops in a riot of colour and Romantic extravagance. From the palace, a curated route winds through the park’s forested paths and viewpoints, passing the Cruz Alta – the highest point of the serra, with breathtaking views over the coast and the Tagus estuary – before continuing to the Moorish Castle, whose ancient battlements offer some of the finest panoramic views in the region. The descent returns through the woodland paths of the serra back into the historic centre, bringing the tour to a memorable and fitting close.

There are regular bus and train connections from Sintra to Lisbon. Your hosts can usually provide the most accurate local details, but if you need additional guidance, our team is happy to help.