Lisbon to Sintra - History, Heritage & Coastal Trails

Self Guided - 8 Days / 7 Nights

Once ruled by the Romans and Moors, Portugal has a glorious and adventurous past, which is clearly seen in its diverse architectural styles, local traditions, extensive beaches, luxurious landscapes and UNESCO World Heritage listed monuments.
This walk follows footpaths through the Sintra-Cascais Natural Park, easily accessible from Lisbon and filled with colourful castles, palaces and monasteries dating from the 13th century. As dusk falls, soak up the ambience of authentic restaurants and bars in Portugal’s towns and villages where delicious fresh seafood awaits you.
Highlights include:

  • The romantic Pena Palace is a UNESCO World Heritage site and one of the Seven Wonders of Portugal.
  • Stunning inland and coastal trails through Sintra-Cascais Natural Park
  • Exploring the impressive “cork” convent of Capuchos
  • Spending time in the lovely seaside cosmopolitan town of Cascais,
  • Stay in a 13th century convent and charming ‘quinta’ (country estate)
  • Awe-inspiring views from Sintra’s Montserrate Palace

Your Journey

Day 1 Arrive Cascais

Transfer from Lisbon Airport to the delightful seaside town of Cascais with its trio of beautiful bays and delightful old town.

Day 2 Guincho Beach to Azóla (Walking: 9km, 400m elevation gain)

As today's walk is quite short you may wish to spend some extra time exploring Cascais. From the golden beach of Guincho make your way over the beach dunes on board walks then cross the beach and follow the rugged coastline to reach the São Saturnino Convent at the head of a secluded valley. Your two-night stay here will be a unique and unforgettable experience. Each room has open beams, antique furniture and its own special charm.

Day 3 Azóla Inland Loop (Walking: 10km, 300m elevation gain)

Today a circuit walk takes you into the Sintra Hills. This route goes up to one of the highest points in the area with stunning views from the hill-top chapel at Peninha. Descend on pretty trails that overlook the Atlantic.

Day 4 Walk to Colares (Walking: 15km; 450m elevation gain)

Experience great coastal walking with beautiful scenery over cliffs to reach Cape Roca, Europe’s westernmost point, a rocky promontory once considered to be the edge of the world. Descend to the wild and beautiful beach of Ursa and lovely Adraga beach, a great lunch stop as there is a restaurant that serves delicious and traditional food. Leave the coast and turn inland through pine forest to reach Pé da Serra. Stay two nights in a charming guest house with ocean views in a serene setting within the rural hills of the Sintra Natural Park.

Day 5 Colares

Enjoy a circuit walk today into the heart of the Sintra forest and hills. En route, there will be a chance to visit the remarkable Capuchos Convent, also known as the “Cork Convent”, because of its corked-lined miniscule cells. Squeeze through the warren of cells, chapels, kitchens and caverns. The monks lived a simple, touchingly well-ordered life in this idyllic, yet spartan place. Descend to the village of Colares, for lunch and perhaps a wine tasting at the Colares Winery. Return through the hills to your ‘quinta’.

Day 6 Walk to Sintra (Walking: 13km, 500m elevation gain)

Follow forest trails in the Sintra hills to the impressive Monserrate Palace, a Neo-Gothic mansion set within fine landscaped gardens. Continue to the town of Sintra, a UNESCO World Heritage site where you'll spend your last two nights in a charming period hotel with spacious and rustically furnished rooms.

Day 7 Sintra Inland Loop (Walking: 7 km, 450m elevation gain)

Spend your day exploring the scenic hills above Sintra village, passing by castles, palaces and old manor houses. Such is the grandeur and importance of these buildings and monuments that Sintra was designated a UNESCO World Heritage Site in 1995.
Pass by two of the most important monuments of Sintra; the amazing Moorish Castle and the Pena Palace situated high on a hilltop, with impressive multi-coloured turrets, dramatic architecture and exotic gardens. Many of these castles and palaces were built by Portuguese aristocracy in the 13th century.

Day 8 Arrangments end

The tour finishes after breakfast with a transfer to Lisbon.


Moderate to challenging - Coastal paths and forest tracks with some challenging hills, a good level of fitness required.


Breakfast daily


2019 cost per person in Euro

Low Season (27 March-13 April, 21 April-26 May, 27 September-03 October):Double/twin share €1166,

Single Supplement if travelling with others €439, additional Solo traveller supplement on request.

Mid Season (14-20 April, 27 May-26 June, 30 August-26 September): Share Twin - €1215. Single supplement - €499.

High Season (27 June-29 August): Share Twin - €100. Single room supplement - €499.

Off Peak (01 January-26 March, 04 October-23 December ): Share Twin - €1099. Single  supplement - €409.


2019: Start any day from 01 January to 23 December.  July & August are not advisable due to the heat.


The above is a short synopsis of this tour. This email address is being protected from spambots. You need JavaScript enabled to view it. for a more detailed itinerary and trip notes.







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A Walker’s World has been offering walking holidays in Europe and around the world since 1991.

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