5-Day / 4-Night Gentle

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.

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.

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. A bus brings you 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.