5-Day / 4-Night Gentle

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 — its medieval Alfama quarter, Moorish castle, grand riverside boulevards and famous tiled façades combining to create one of the continent’s most rewarding cities to explore on foot.

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.

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.