9-Day / 8-Night Moderate

From your point of arrival, use the public transport information we provide to make your way to vibrant Lisbon, one of Europe’s most captivating capitals. Perched above the Tagus estuary on a series of dramatic hills, Portugal’s sun-drenched capital is a city of extraordinary character and one of the continent’s most rewarding cities to explore on foot. And if you arrive with time to spare, why not set out on our self-guided walking tour through some of Lisbon’s oldest and most atmospheric quarters – from the Baixa up through the Moorish quarter and hilltop Graça, down through the winding lanes of the Alfama to Castelo de São Jorge, and back to the elegant riverside square of Praça do Comércio.

A leisurely walk but a day packed with history. Following the north bank of the Tagus westward from Lisbon’s grand waterfront square, you trace the very edge of Portugal’s maritime world – the river from which Vasco da Gama and the great navigators set sail during the Age of Discovery in the 15th and 16th centuries. Historic naval facilities and old dockyards give way to modern marinas and cultural landmarks. After passing beneath the sweeping cables of the Ponte 25 de Abril, the city gradually opens out into the quieter district of Belém. Here, a remarkable concentration of monuments, museums, and memories awaits: two UNESCO World Heritage Sites in the Jerónimos Monastery and the Torre de Belém, along with Portugal’s most famous custard tart, best eaten warm from the bakery that invented it.

A rewarding day of contrasts, taking you from the elegant resort town of Cascais along one of Portugal’s most dramatic stretches of Atlantic coastline before climbing into the wild foothills of the Sintra hills. The walk begins with an exploration of Cascais itself before a short transfer brings you to Cabo Raso where you follow the coast – a rugged, elemental landscape of lighthouses, crumbling fortresses, rocky headlands, sandy beaches, and windswept dunes, with cafés along the way to break the journey.

Roughly halfway, the character of the walk changes as the trail leaves the shore and begins to climb into the Sintra foothills, trading crashing waves for rolling hills and views back along the coast in a welcome change of pace and scenery. Here, the trails will challenge you a little more with short, more rugged up and down sections that require surefootedness. Quiet tracks then lead you to the village of Azoia, which lies perched on the western edge of the Sintra hills.

A lovely loop hike through the heart of the Serra de Sintra. Despite its modest distance, the walk packs in an extraordinary range of scenery, history, and prehistory – from sweeping Atlantic viewpoints to ancient megalithic tombs and a medieval convent hidden deep in the forest.

The route climbs first 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 the dense old-growth oak forest surrounding the Convento dos Capuchos, the remarkable 16th century Cork Convent where Franciscan monks lived in austere cave-like cells for three centuries. On the return journey, a short detour leads to the mysterious Anta de Adrenunes megalithic monument.

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.

Starting from the Palácio Nacional de Sintra, this short loop passes the intriguing Quinta do Relógio – a Neo-Arabic palace whose entrance bears the motto of the Emir of Granada – before reaching the captivating Quinta da Regaleira, saturated with Templar and Freemasonic symbolism, its famous Initiation Well descending 27 metres into underground tunnels and grottoes. Continuing west, the walk passes the serene Palácio de Seteais, a neoclassical 18th-century palace now an elegant hotel, before a narrow path climbs the wooded hillside towards Pena Park. The descent follows a romantic forest trail past the charming Vila Sassetti and its terraced gardens, before dropping back into the historic centre and a visit to the Palácio Nacional de Sintra – one of Europe’s oldest royal residences and the only palace that spans 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 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.