On our cycling tour through Sintra (Sintra–Cascais Bike Tour), we ride along paths where history and nature have met for centuries. This is a land inhabited since Antiquity, long associated with the sacred, with royalty and later with Romanticism. This unique connection between landscape and heritage led Sintra to be classified as a UNESCO World Heritage Cultural Landscape in 1995.
Cycling through Sintra is a journey across different eras — feeling the mountains, breathing in the forest air and discovering why this place is considered truly magical.
The history of Sintra, following the rhythm of the ride
The tour begins in the historic center of Sintra, next to the Sintra National Palace, also known as the Town Palace. Its origins date back to the 10th century, during the Islamic period, although it was extensively transformed after the Christian Reconquest of 1147. Between the 14th and 19th centuries, it became a regular residence of the Portuguese monarchy, making it the oldest royal palace in Portugal still in use.
We then continue to the Quinta da Regaleira, built between 1904 and 1910 by António Augusto Carvalho Monteiro. This remarkable estate reflects the spirit of the early 20th century, shaped by symbolism, esotericism and the influence of Templar ideals. Its gardens, underground tunnels and the famous Initiation Well represent a symbolic journey between earth and knowledge.
The route continues to the Seteais Palace, built at the end of the 18th century (1783) as an aristocratic residence. Today, it offers one of Sintra’s most iconic viewpoints, with a direct view of the Pena Palace, constructed in the 19th century by King Ferdinand II on the ruins of a former 16th-century monastery.
As we ride further, the landscape becomes increasingly green and serene as we pass by the Monserrate Palace, rebuilt between 1858 and 1866 by Sir Francis Cook. A remarkable example of Romantic architecture, the palace stands out for its blend of Oriental, Gothic and Islamic styles, set within a botanical garden featuring species brought from all over the world.
A land shaped by centuries
Long before the Romantic palaces, Sintra was already a strategic stronghold. During the Muslim occupation, between the 8th and 12th centuries, a defensive line was built along the hills, including what is now known as the Moorish Castle, a reminder of the region’s military and geographical importance.
Over the centuries, Sintra evolved from a defensive fortress into a royal retreat and later into a center of artistic and cultural inspiration.
The ride is only just beginning
After Monserrate, the tour continues through the hills, heading toward the coast and Cascais — marking the beginning of the next stage of the journey.
