Sintra & Cascais

After a 30-minute private transfer, you will receive a warm welcome in the charming town of Cascais. Depending on when you arrive, it is recommended that you spend some time exploring the town. First settled by fishermen 650 years ago and later taken over by various societies, Cascais offers a rich history and many attractions. Finish the evening by a dinner including the local seafood.

The day begins with a short transfer to Guincho, where the day’s hiking route begins. You will experience a wide coastline with high sand dunes, valleys and small, charming villages where a rural atmosphere meets a luxurious one in a wonderful synergy. Today’s goal will be to reach the hotel Convento de Saõ Saturnino, where the night will be spent. This old monastery offers a magnificent view over the horizon, where the mountains and the sea meet.
10 km (18km), + 300 m (+ 400 m)

Today you will be hiking around the surroundings of Azóia, where you will see Mount Sintra and its fabulous views. You will start by climbing the ‘Moon hills’ as Sintra mountain is also known as. It is a climb to 488 metres above sea level. From the top you will have a beautiful 360 degree view of the surroundings including the forests, the sea and the beautiful landscape. A perfect place to enjoy the silence and tranquillity!
10 km, + 300 m

After a nice breakfast and replenished energy stores, a hilly landscape awaits you with the sea on the horizon as far as the eye can see. After a short hike, you’ll reach Cabo da Roca, Europe’s westernmost point on the mainland. Here you can admire the beautiful lighthouse that dates back to 1772. From Cabo da Roca, the day’s hike continues along a wild and beautiful beach called Ursa. The hike continues along the beach of Adraga, which is ideal for a lunch break. Finally, you will arrive at today’s destination, Praia Grande, where the hotel is located on the beach.
12 km, +200 m

Today’s hike starts along forest paths leading to to the Monserrate estate. This manor house, with its neo-Gothic architecture, is a shining example of the Romantic period that has left a strong imprint on the area around the village of Sintra. From here, you have two options for the rest of the day, depending on how far you want to hike.
Once in Sintra, you can stroll along the romantic streets, and why not savour some of the regional pastries?
19 km (13 km), +600 m (+400 m)

Today you will have time to explore the surroundings of Sintra. The landscape offers a varied terrain on the hill above the village of Sintra. In 1995, the cultural landscape around Sintra was designated as a World Heritage Site by UNESCO. It is recommended to visit the Moorish castle and the marvellous Pena Palace, which offers exclusive and exotic gardens.
End the day with a delicious dinner in one of the restaurants in the centre of Sintra.
7 km, +300 m

We hope you have enjoyed the amazing environment that this hiking holiday has offered. Our guide will pick you up at your hotel for a private transfer to Lisbon airport, or into Lisbon if you intend to stay there for a few days after the hiking tour.

Our guide will pick you up and drive you to your first accommodation in Sintra. Sintra is a magical, mysterious and medieval place. Surrounded by a stunning landscape of rolling mountains and lush forests, with palaces, villas and beautiful gardens. Explore this incredible Unesco World Heritage Site and enjoy its historic centre and its famous pastry called Queijada de Sintra.

Today you will have time to explore the surroundings of Sintra. The landscape offers a varied terrain on the hill above the village of Sintra. In 1995, the cultural landscape around Sintra was designated as a World Heritage Site by UNESCO. It is recommended to visit the Moorish castle and the marvellous Pena Palace, which offers exclusive and exotic gardens.
End the day with a delicious dinner in one of the restaurants in the centre of Sintra.
7 km, +300 m

Today you will cross the hills of Sintra and its mysterious environment. Surrounded by its beauty, you will find the ‘Capuchos Monastery’, built in stone and surrounded by greenery. From here, the path leads you towards Praia Grande and its dramatic cliffs. Crossing the Sintra-Cascais Natural Park, you’ll also reach Colares, a quiet town famous for its wine and pastries.
17 km, +400 m

Today you will experience the landscape over the cliffs, where the sea stretches as far as the eyes can see. You will follow a coastal path towards Azoia, between beautiful and isolated beaches. At Adraga beach you can see the Pedra de Alvidrar, also known as the ‘Rock of Reason’, a huge rock formation that falls almost vertically into the sea and which, according to local tradition, was a place for young men to prove their bravery by climbing up and down it, at great risk to their lives. Next, you will conquer Cabo da Roca, which is the westernmost point of the European mainland. On the way back to Praia Grande, you will pass through small and picturesque villages.
18 km, +500 m

The day starts with a short transfer to Peninha, one of the highlights of the Serra de Sintra. From here you continue towards the sea and enjoy spectacular views of the entire Sintra coastline, while hiking on nice trails in the forest. With the sea on your right, you’ll head towards Cascais, alternating between lovely beaches and a hilly and rocky coastline. You will pass the 17th century fortress ‘Fortaleza do Guincho’, which is now a renovated hotel. Almost at the end, very close to the village of Cascais, you will also pass ‘Boca do inferno’, a dramatic coastal spot with stunning views.
19 km, +170 m

We hope you had a great trip! Either organise your own transport to the airport, or book a transfer through us. Or, you might want to take the opportunity to visit Lisbon or have a few extra days in Cascais?