9-Day / 8-Night Moderate

From your point of arrival, use the public transport information we provide to make your way to Lisbon, one of Europe’s most captivating capitals – a city of medieval quarters, Moorish castles, grand riverside boulevards and famous tiled façades, perched above the Tagus on a series of dramatic hills and best explored on foot.

Optional: Starting from the lively squares at the northern edge of Lisbon’s 18th-century downtown, the route climbs into the old city, with sweeping views opening up at Graça. The descent winds through the Alfama, a labyrinth of cobblestone lanes, tiled houses and drifting Fado music, and past a series of celebrated miradouros to the medieval Castelo de São Jorge, perched at the city’s highest point. From there the route descends to the grand riverside square of Praça do Comércio.

The above does not include the time required to visit the many attractions, eating Pastel de Nata, or to sit and enjoy the views of the river.

Following the north bank of the Tagus westward from Lisbon’s grand waterfront, the route traces the edge of Portugal’s maritime world and the river from which the great navigators once set sail. Historic dockyards and naval facilities give way to modern marinas before the city opens out into the quieter district of Belém, where two UNESCO World Heritage Sites, the Jerónimos Monastery and the Torre de Belém, await alongside Portugal’s most famous custard tart, best eaten warm from the bakery that invented it. From there, take a train along the Estoril coast to the elegant resort town of Cascais.

The walk begins with a brief exploration of Cascais before a short transfer to Cabo Raso, where the trail follows one of Portugal’s most dramatic stretches of Atlantic coastline – lighthouses, crumbling fortresses, rocky headlands and windswept dunes, with cafés along the way. The character changes as the trail leaves the shore and climbs into the Sintra foothills, trading crashing waves for rolling hills and views back along the coast. The terrain here is more rugged, with short up-and-down sections requiring sure-footedness, before quiet tracks lead to the village of Azoia, perched on the western edge of the Sintra hills.

Despite its modest distance, this loop through the heart of the Serra de Sintra packs in an extraordinary range of scenery, history and prehistory. The route climbs to the Santuário da Peninha, perched at around 490 metres with panoramic views from Cabo da Roca to Cascais, before crossing the high serra past a 4,000-year-old prehistoric tomb. The descent winds through dense old-growth oak forest to the Convento dos Capuchos, the remarkable 16th-century Cork Convent where monks lived in austere cave-like cells for three centuries, with a short detour on the return to the mysterious Anta de Adrenunes megalithic monument.

You leave the Sintra foothills where they meet the sea at Cabo da Roca, the westernmost point of mainland Europe. Waymarked clifftop paths head north past rocky headlands, hidden beaches and dramatic sea stacks, dipping inland briefly before returning to the coast at the Fojo dos Morcegos, a spectacular sinkhole plunging from the clifftop to the sea. A stop at the beautiful Praia da Adraga offers a coffee or a swim before the final stretch to Praia Grande, where 125-million-year-old dinosaur footprints are embedded in the cliff face.

Note that visiting attractions along the route can add significantly to the required time.  

After a transfer to Colares, the route climbs through woodland to the atmospheric Convento dos Capuchos, a 16th-century Franciscan hermitage with tiny cork-lined cells and hidden chapels carved into the living rock. The trail then winds through the ancient forests of the Serra de Sintra before descending to the Park and Palace of Monserrate – a Victorian masterpiece of neo-Gothic, Moorish and Indian architecture set within botanical gardens and cascading waterways. From there, an ancient path climbs to Sintra, the magical hilltop town of palaces and Romantic follies that has drawn poets, kings and travellers for centuries.

Starting from the historic centre, this short loop visits the Quinta da Regaleira, saturated with Templar and Freemasonic symbolism, where the famous Initiation Well descends 27 metres. The walk continues past the neoclassical Palácio de Seteais before a narrow path climbs the wooded hillside towards Pena Park. The descent follows a romantic forest trail past Vila Sassetti and its terraced gardens, returning to the historic centre and a visit to the Palácio Nacional de Sintra – one of Europe’s oldest royal residences, spanning the entire history of Portugal from its Moorish origins to the fall of the monarchy in 1910.

For many walkers, this is the highlight of their holiday. The ascent from Sintra’s historic centre follows the romantic Vila Sassetti trail to Pena Palace: perched on a rocky crag, its vivid towers and battlements rising above the treetops in a riot of colour and Romantic extravagance. A curated route then winds through the park past 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 and its sweeping panoramas. The descent through woodland returns to the historic centre for 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. Alternatively, you may wish to ask your accommodation for a taxi to the airport.