Walking the Sintra and Cascais landscape is an open window into the past, following routes designed to explore the area’s foremost historical and cultural sites. Discover Sintra’s fascinating sights in the morning, before joining hiking routes out into the area’s peaceful surrounding woodland and rural landscapes later on in the day. Starting in the vibrant town of Sintra, discover the town’s extravagant palaces, gardens and manor houses, with the latter half of the walking holiday located on the breath-taking Atlantic coastline, reaching Azenhas do Mar and the fisherman’s town of Cascais – just one hour away from Lisbon by public transport.
Exploring the castles, palaces and manor houses of Sintra in the morning, you'll find even, well-defined footpaths around the town's palace grounds and surrounding hillsides. As you make your way out into the more rural areas in the afternoon, you follow a more shaded route, under the canopy of the forest along slightly more rugged dirt trails and woodland paths that lead out of the towns historic centre. A combination of circular walks, and sections that follow the established "Costa Atlántica" make up the coastal sections at the end of the itinerary. These routes that lead out of the hillsides to the coast take you through the Sintra-Cascais National Park, a landscape of vibrant colours, beaches and secluded coves.
The footpaths you follow are well way-marked with some steep ascents/descents, designed to accommodate around 4-5 hours walking each day, allowing ample time to experience the traditionally relaxed Portuguese lifestyle in the communities, towns and villages you stay in.
As you walk out from Sintra to the Portuguese coast, you'll find a range of accommodation that reflects the character of the area you're staying in. You'll spend four nights in Sintra, with a sun terrace overlooking Pena Castle and the Sintra Mountain Range. Out on the Praia Grande, our standard accommodation boasts swimming pools and fantastic views over the neighbouring Atlantic. Our accommodations are selected with great care; high-standard, characterful establishments featuring en-suite rooms and many great places to eat (serving traditional Portuguese food) within a short walking distance.
From Lisbon airport, there are convenient public transport options to Sintra (approx. one hour). However, we do offer the option of a private taxi transfer directly to your accommodation.
5.5 miles (9km)
Today's route explores the most prominent monuments of Sintra: Castelo de Mouros, Palacio de Pena and the Palacio National. Start with a steep ascent to the Moorish castle and colourful palace of King Ferdinand, followed by a tour of the spacious palace grounds, before joining the path that descends sharply via Vila Sasseti to the town centre of Sintra, where the National Palace stands. 475 ascent/descent, mainly on good paths, the descent is rather steep. Est. walking time 4 - 4.5 hours. Note: you can avoid the steep ascent and descent by taking the bus (approz. €5).
Convento dos Capuchos - Azoia
7.1 miles (11.5km)
Venture further out of the town with a transfer to the austere 16th century Franciscan monastery of Convento de los Capuchos, of which you have time to explore the grounds before setting off on today's walk. Today's route leads you through enchanting Mediterranean woodland, scattered with hillside menhirs and the shrine dedicated to the Virgin Mary of Peninha. The path then descends to Azoia, where the taxi is waiting; you may also wish to stop off at Azoia for a typical Portuguese lunch before returning to Sintra. 425 ascent/descent, mainly on good paths, the descent is rather steep. Est. walking time 4.5 hours.
Sintra Manor Houses
4.5 miles (7km)
Today's route delves into some of the more impressive and noteworthy palaces and manor houses of Sintra. Within a few square kilometres, you have a collection of extravagant buildings open for exploration, starting with: "Quinta da Regaleira", a romantic, and quite ominous early 20th century palace built by an eccentric Brazilian coffee farmer and Freemason. He constructed a series of spiraling underground tunnels connected to the palace for his groups' secretive masonic rites. "Palacio de Setais", a 18th century Neoclassical palace, which is now a hotel where the extensive gardens are open to visitors. From here, you can take the 435 bus, or walk 2.5km along the road to reach. "Palacio de Montserrat", a Romantic building with Indian and Arabic influences, built by a Portugeuse-English Viscount and industrial magnate.
Sintra to Azenha do Mar
9.3 miles (15km)
Sintra's grand palaces are left behind with a route that stretches out through fields, vineyards and pine forests to the picturesque fishing village of Azenhas do Mar. You stay overnight on the "Praia Grande" in Arribas, in a hotel that comes with its own large saltwater and smaller freshwater swimming pools. 300m ascent/ 500m descent. Est. walking time 4.5 hours.
You can also take a shorter route via the 19th century tram to Azenha (runs Thursday to Sunday) and walk just the last few kilometres, or take the bus directly to the Praia Grande (line 439), where you can stay 2 nights in the renovated "Arribas" beach hotel. All rooms have a terrace and sea views, with a range of restaurants nearby.
Circular Route from Praia Grande
7-7.5 miles (11.3-12 km)
From Hotel Arribas you follow the long distance walking path - the GR-11 "Costa Atlántica" - that travels south along the fisherman's trails of the coast to the village of Ulgueira. From here, you can walk to Costa to Roca and back, or loop back to Praia Grande via a different route.
475m ascent/ 550m descent. Est. walking time 4.5 - 5 hours.
Azoia - Guincho (Cascais)
5-10 miles (8-17 km)
Transfer to Azoia, where your join the GR-11 as it follows the coastline to the 17th century fortress of "Fortaleza de Guincho", now a luxury hotel with views over Praia do Guincho. You have the option of leaving the route halfway (at approx. 7.5km) and taking the bus directly to Cascais, or walking an additional 9.5km to your hotel (footpath between the road and beach).
175 or 275m ascent/375 or 475m descent. Est. walking time 3 - 5.5 hours. Bus to Cascais (Line 415 or 405).
After breakfast, you have the option of travelling back to Lisbon via public transport (one hour). Alternatively, we can arrange a private transfer.
Transfers to/from the path (where indicated in the programme)
A Destination Manual and Road Book (route notes) showing directions to your directions and a local map
Extra night in Lisbon
Packed lunches: can be ordered either from your accommodation, or bought locally each day
Evening meals: Local Restaurants or in-house at your accommodation
Postage overseas - £5.00 (Europe), £10,00 (Rest of World), per Walk Pack
You choose which day you would like your holiday to start on. We will book your holiday in accordance with your requirements.
Our Sintra – Cascais holidays are available to walk January to June, September to December.
The best time to visit Sintra would be Spring and early Autumn. The days are bright and temperate, and the summer crowds have long since decamped. During the high season, the town's historic centre can get quite busy from midday onward, and the heat can make progress that much more difficult.
Travel arrangements for arrival/departure:
You are responsible for booking your travel to Portugal and to your accommodation in Sintra and return from your accommodation in Cascais.
Looking for different mileages or different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs. Call one of our helpful team on +44 (0)1291 689774 or e-mail us to learn more.
Sintra – Cascais Client Reviews
5/5 based on 2 reviews
I haven't felt this good in a while - both in body and spirit.
The feeling of connection to the land was overwhelming. The people were incredibly warm and friendly. Did I mention the wonderful hospitality and food?
A tough choice between Portugal and Tuscany. May yet do Tuscany with this company. A. Headburg - March 2019
Thoroughly enjoyed the experience - shall book with you again. Thank you. M. Brown - December 2018
Leave your own review of your Sintra – Cascais Walking Holiday with us - add review.
We will check your details and come back to you within two working days with a personalised estimate based on your requirements. We will then formally request a deposit of £100 per person (£100 per person for a single centre break) and book all your arrangements - find out about our full booking process here.
Please note this does not constitute a booking confirmation, we kindly ask you to refrain from booking any travel until we have confirmed all your arrangements.
Still Have Questions?
If you are still unsure on any of your requirements, please do enquire with us first and one of our friendly team will be happy to help you with any queries you have.