Walking Sintra to Cascais

The UNESCO World Heritage site of Sintra is just a 40min direct train ride away from nearby Lisbon. Stroll around the historic centre, soaking up the atmosphere of this wonderfully vibrant, colourful town and perhaps visit the Palacio Nacional de Sintra, a Gothic palace featuring ornately painted ceilings. In the evening, sit back, relax and enjoy dinner in one of the many cosy restaurants serving delicious Portuguese specialities such as the tasty Bacelhau a bras cod dish.

Today is dedicated to discovering the extravagant palaces, manor houses and castle of Sintra. First stop is the Quinta Regaleira, a lavish mansion and former home to Portuguese nobility. With it’s enchanting, tropical gardens and lots of hidden caves, tunnels and wells, you can easily spend a couple of hours here. Continue on foot, following a peaceful wooded trail uphill to the Pena Palace, with its impressive multi-coloured turrets, dramatic architecture and exotic gardens. Finally, visit the amazing Castel dos Mouros (Moors Castle) which sits right on top of the hill and offers amazing views over Sintra. Head back to the centre of Sintra via a tranquil stepped forest path.

Please note that entrance fees to the above are not included to keep your day flexible, and we recommend booking in advance to avoid the sometimes long entrance queues. The distance detailed is also only to entrance gates of the attractions - you will actually walk quite a bit further by the time you have walked around all of them!

Ascent/Descent: +219m/-219m

Leaving Sintra, follow forest trails into the Sintra hills, stopping off to visit the fantastic Monserrate Palace, a Neo-Gothic mansion set within landscaped gardens. Take your time to explore the gardens which were built by a series of wealthy British merchants and artists. Continue to Colares, a unique wine region  where the vineyards grow across the sand and produce delicious red and white wines from the ramisco or malvasia grapes.  In the village of Colares itself, you may like to visit the Colares Regional Winery, founded in 1931, and the oldest co-operative winery in Portugal.

A pre-arranged transfer will take you from Colares to Azoia late this afternoon, where you can check into the romantic São Saturnino Convent, lovingly restored from 13th century ruins. Your stay at this hotel with its labyrinthine interior and tranquil setting in a hidden valley is sure to be a unique and very memorable experience.

Ascent/Descent: +320m/-508m

A loop walk today takes you into the heart of the Sintra forest and “Moon Hills” (so called because the ancient Celts worshipped their moon god here). First stop is the one of the highest points in the area where you will find the hill-top Peninha Chapel with far-reaching views across the countryside. Dedicated to Our Lady of the Rock, it is said that in the past sailor’s wives would come here to keep watch for the return of loved ones.

Continue through the forest to the remarkable Capuchos Convent, also known as the “Cork Convent”, because of its cork-lined tiny cells. Spend some time exploring the warren of ruins, where monks previously lived a simple life in this idyllic location. Descend to the little village of Pe da Serra, where you may like to enjoy a late lunch before returning to Azoia.

Ascent/Descent: +540m/-540m

Head to the rugged Atlantic coast, and enjoy a walk to Praia Adraga. Leaving Azoia you soon reach Cabo da Roca, Europe’s most westernmost point and once considered to be the edge of the world.

Continue walking on clifftop paths accompanied by views over the blue ocean and wind your way down to the beautiful golden beaches of Ursa and Adraga. Stop for lunch at the beachside restaurant and then turn inland,  passing through a pine forest and the traditional village of Ulgueira before heading back to Azoia.

Ascent/Descent: +345m/-330m

Leave Azoia and the “Serra da Sintra” this morning and return to the rugged coastline following winding paths on the GR11 to the 17th century fort “Fortaleza de Guincho” (now a hotel). From here, it is a very easy walk following a path between the road and the ocean passing lighthouses and interesting cliff formations to reach Cascais. If you prefer, you can take a bus straight to Cascais from Guincho which shortens the day by 9km.

Ascent/Descent: +145m/-325m

You have a full day to explore and enjoy the delightful seaside town of Cascais with its trio of beautiful bays. Wander through its pedestrianized old town and along the marina before eating alfresco in one of the many local seafood restaurants, perhaps sampling some of the tasty fresh Bacalhau (cod).  In the evening there is also a very good bar, where musicians perform traditional fado music which is incredibly haunting (worth booking in advance if this is your cup of tea!)

Check out after breakfast and make your way by train back to Lisbon for onward travel connections (40 min).