The Routes
These tours combine the very best walking in and around Lisbon with the most rewarding trails of the Sintra-Cascais Natural Park. Depending on which itinerary you choose, your tour may not include every walk described below or may cover the finest sections of each. From the medieval quarters of Lisbon to the Atlantic clifftops of the natural park, these trails move through a landscape of extraordinary contrasts – royal palaces and ancient hermitages, dramatic sea cliffs and forested mountain ridges, a world-class capital city and some of the wildest coastline in western Europe.
All tours begin in Lisbon, often starting with a looped city walk threading through the Baixa, the Moorish quarter and the hilltop neighbourhood of Graça, before winding through the Alfama’s narrow lanes to Castelo de São Jorge. The walk returns to the elegant riverside square of Praça do Comércio, where the river opens out and the city feels at its most grand.
A highlight of these tours follows the River Tagus west past the old docks, shipyards and maritime heritage of Lisbon’s great seafaring waterfront to Belém, where the Manueline towers of the Torre de Belém and the soaring cloisters of the Jerónimos Monastery mark the point from which Portugal’s great explorers once set sail. A short train ride along the Estoril coast then brings walkers to Cascais, a handsome resort town and former royal summer residence where the Atlantic makes itself felt for the first time.
From Cascais, the tours enter the Sintra-Cascais Natural Park in earnest, passing the thundering blowhole of Boca do Inferno before a transfer to Cabo Raso, from where the trail follows the clifftops and foothills south through open heathland to the quiet village of Azoia. A contrasting looped walk strikes into the heart of the Serra de Sintra, climbing to the Sanctuary of Peninha with its sweeping coastal views, then on past the prehistoric Tholos do Monge to the extraordinary Convento dos Capuchos – a Franciscan hermitage of moss-covered cells tucked deep into the rocks.
Returning to the coast, the trail continues from Azoia to Cabo de Roca – the westernmost point of continental Europe – and north along one of the tour’s most dramatic sections: past sea stacks, the cave of Fojo dos Morcegos, the secluded Praia da Adraga and dinosaur footprints preserved in the coastal rock, finishing at the broad sands of Praia Grande. The natural park’s northern coast is then explored on a walk from Praia do Magoito south via the clifftop hamlet of Azenhas do Mar. From Colares, an inland route climbs through the Serra de Sintra, passing the Convento dos Capuchos and the exotic gardens and Moorish-Gothic palace of Monserrate before dropping into the World Heritage town of Sintra.
Two walks are devoted to Sintra’s forested ridges and remarkable concentration of historic sites. A looped walk from the historic centre visits Quinta da Regaleira and its mysterious Initiation Well, passes the elegant Palácio de Seteais and climbs to the edge of Pena Park, before descending via a romantic forest trail past Vila Sassetti to the Palácio Nacional de Sintra.
A second, longer walk – one of the undoubted highlights of these tours – makes the ascent to Pena Palace, by foot via the romantic Vila Sassetti trail or by bus for those who prefer an easier start to the day. Perched dramatically above the treetops on a rocky crag, Pena Palace is one of the most extraordinary royal residences in Europe, its vivid towers and battlements rising above the forest in a riot of colour and Romantic excess. A curated walk through the palace park explores the wilder corners of the serra before the trail climbs to the Moorish Castle, whose ancient battlements offer some of the finest panoramic views in the region – the serra’s forested ridges on one side, the glittering Atlantic on the other. The descent back into Sintra brings the tour to a fitting and memorable close in one of Europe’s most enchanting landscapes.
Terrain Overview
These routes offer a rich mix of terrain, from easy urban trails and riverfront promenades to rugged Atlantic clifftops, forested mountain paths and open heathland. In Lisbon, the walks follow cobbled streets and well-maintained paths, with some short steep climbs between the city’s famous hills. The riverside walk to Belém is largely flat and easy underfoot.
West of Cascais the terrain becomes wilder, with coastal and cliff-side paths, heathland tracks and rocky shoreline. The stretch from Azoia past Praia da Adraga to Praia Grande is particularly dramatic, alternating between clifftop paths, valley trails and short descents to the coast, with some rougher sections requiring reasonable sure-footedness. The northern coastal trails between Praia do Magoito and Azenhas do Mar are more manageable, with gentle undulation above the Atlantic.
In the Serra de Sintra, the trails are predominantly forest and woodland paths, sometimes narrow but rarely very steep. The Peninha loop involves some more sustained climbing, while the inland route from Colares includes a long steady ascent through woodland, which can be skipped with a transfer to the Convento dos Capuchos. The Sintra town walks combine well-maintained park paths with steeper woodland trails on the descent and ascent past Vila Sassetti.
None of these hikes are longer than 15km (10 miles). Overall, these tours suit most walkers, though some days include a significant amount of ascent and descent and some experience of uneven terrain is helpful. The coastal sections involve clifftop paths close to exposed edges and the walks around Sintra include some exposed high ground and castle battlements. We do not recommend these tours for walkers with vertigo or a fear of heights.
