Lisbon & Sintra In Style

A private transfer (duration: 1h) will whisk you from Lisbon to your luxurious eco-conscious beach retreat at Santa Cruz on Portugal's Costa de Prata (Silver Coast), where you can unwind and soak up the sea breeze in a magical setting. Kick-start your journey with a drink by the bonfire, with the Atlantic Ocean in view. Looking south you will see the Ponta da Vigia cliffs, where the Penedo do Guincho boulder arises. On clear days, it is possible to take in sweeping panoramic views that extend as far as the Cabo Carvoeiro lighthouse and the Berlengas islands.

The inland village of Vimeiro is the starting point for today's hike back to Santa Cruz. Famous for its hot springs, Vimeiro is a peaceful village with an impressive history, namely an important battle that took place there during the Napoleonic invasions, in the 19th century. After a quick transfer (duration: 15min) to the village, the path will take you along the Alcabrichel River, towards the coast, and to Porto Novo beach. This beautiful beach is located on the lower extent of a beautiful valley. Historically a fishing port, this place also takes place in the history books and it is an important heritage to Vimeiro. Once close to the Atlantic, you will continue south, exploring the many impressive beaches on the coast until reaching your accommodation in Santa Cruz.

Elevation: +100m/+328ft

A private transfer (duration: 45min) takes you to the small town of Colares, famous for its pastries and wine, and the starting point for your hike today, so why not stock up on those pastries? The path climbs up the sierra, with the fragrances of the thickening forest accompanying you. After crossing some forest trails on the hills, you will reach the Monserrate Palace, a Neo-Gothic mansion set within amazing landscaped gardens. Take some time to explore the house and the beautiful gardens. The Park and Palace of Monserrate were classified as a Property of Public Interest in 1993 and were included in the Cultural Landscape of Sintra, which has been classified by UNESCO as a World Heritage. This palace has Gothic, Indian, and Moorish influences in its different rooms with exotic plant motifs. The overwhelming beauty of its interior sprawls to the exterior (or maybe it’s the other way around), in one of the most impressive Portuguese botanical gardens.

After visiting this beautiful palace, you have two options: continue walking to Sintra where you'll stay for the next two nights, or take a taxi or bus there (payable locally). The arrival in Sintra is special, with a long descent taking you right into Sintra, with fantastic views. It's a spectacular way to finish today's walk.

Elevation: +600m/+1,969ft

Take in the regal palaces, castles and monasteries of Sintra on a fabulous circular hike through the surrounding emerald green landscape. Today is all about discovering Sintra, with the amazing Castel dos Mouros (Moors Castle), which sits right on top of the hill, offering amazing views over Sintra. Continue on foot, following a peaceful wooded trail uphill to the Pena Palace, with its impressive multi-coloured turrets, dramatic architecture and exotic gardens. If you have time we also recommend visiting the Quinta Regaleira, a lavish mansion and former home to Portuguese nobility. With its enchanting, tropical gardens and lots of hidden caves, tunnels and wells, you can easily spend a couple of hours here. 

Elevation: +400m/+1,312ft

*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! A shorter 8km loop is therefore available should you wish to opt for this instead.

Start the day at Convento dos Capuchos after a short transfer from Sintra (duration: 15min). Capuchos is a classic example of an austere 16th-century Franciscan monastery that you can visit before setting off on your walk (tickets not included, payable locally). Then, from here, your walking route will lead you towards Praia Grande and its dramatic cliffs.

Capuchos Convent, also called Cork Convent, is an incredible experience as you explore the warren of cells, chapels, kitchen, and cavern in it. The convent entrance door offers two possible paths, symbolising free will, and is a good introduction to the forward-thinking of these monks. The monks' life was marked by simplicity and touchingly well-ordered life. After spending some time exploring the Convent, start your hike along the fantastic woods of the Sintra-Cascais Natural Park, with its luxuriant green vegetation and the smell of the sea air all around. The final part of the stage will be an approach to the sea.

You will see the beautiful beach of Adraga, where you can see the Pedra de Alvidrar, also known as the “Rock of Reason”, a huge rock formation that drops almost vertically into the sea, and according to the local tradition was an initiation place for young men to prove how brave they were, by climbing up and down it, at huge risk for their lives. Then, you will reach Praia Grande, where a transfer (duration: 30min) to Cascais will be waiting for you.

Elevation: +353m/+1158ft

Please note: Until the end of May 2026 the some sections of the normal route to Praia Grande are not accessible to walk. Instead, you will Stop in Praia Adraga, where a pre-booked taxi will pick you up and take you to your overnight accommodation.

The day starts with a short transfer (duration: 30min) to Peninha, one of the highlights of the Serra de Sintra. This is where the sun and the moon present two great moments; the farewell of the first behind the Atlantic and the birth of the second in the clear skies of the Serra. From here, continue towards the sea, and admire the spectacular views of the entire Sintra coast while walking along enchanting paths within the forest. Then, keeping the ocean to your right, walk towards Cascais, alternating between incredible beaches and a rugged and rocky coastline. This is an area heavily fortified since it was Lisbon’s first-line defense. End your walk at Guincho Beach before getting transferred back (duration: 15min) to your hotel in Cascais.

Elevation: +108m/+354ft

The morning is dedicated to exploring Cascais. Use your free time exploring its historic monuments and museums, admiring its elegant palaces or just walking along its pretty coastal footpath. 

A trip to Portugal isn't complete without exploring Portugal's thriving capital, Lisbon. So now that your hiking has come to an end, a private transfer (duration: 45min) will whisk you to this much-loved city. Many people instantly fall in love with it as they wander the medieval cobbled streets of the picture-perfect Alfama neighbourhood, home to the stunning 12th-century Sé de Lisboa Cathedral. A climb to the top of the city’s famous “seven hills” is also a must, for the panoramic views of the city and the ocean. Or why not visit the Castelo de Sao Jorge (St George’s Castle), with its amazing views over the Tegus River. Quirky neighbourhoods are aplenty in Lisbon, so hop on board the city’s iconic tram and head into Bairro Alto, a lively bohemian area full of energy, and where you'll hear the chatter of Lisboans or the melancholic tones of fado seeping from cosy backstreet bars and restaurants. If culture is your thing, Chiado is the neighbourhood for you. Home to numerous theatres, museums and bookshops, and where the great writers and philosophers of the 20th-century used to gather.

Check out after breakfast and make your way back to Lisbon Airport by bus (duration: 20min). Alternatively, contact your Adventure specialist to book a private transfer, or why not book an extra night to explore this fantastic city even further?