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Walking from Sintra Mountains to the Portuguese Riviera

Walking Sintra to Cascais


This unique walking tour will take you from the beautiful resort town of Sintra, located in the foothills of the Sintra Mountains, once a royal sanctuary, to the popular seaside resort of Cascais on the Portuguese Riviera, known for the many members of royalty who have lived there. You will have the opportunity to visit extravagant palaces, manor houses and lush gardens included in the UNESCO World Heritage List and do some easy walks on picturesque coastal trails

  • The UNESCO World Heritage Site of Sintra
  • Feast on delicious fresh seafood
  • The lovely seaside town of Cascais
  • Walk from tranquil wooded hills to the rugged Atlantic coast

Click to view map


Day 1: Arrive Sintra

Sintra is only 23 km away from Lisbon, and you will easily reach it by taking a train from the Portuguese capital. When you arrive in Sintra, your first accommodation is a family run business just outside Sintra’s town centre that has a quiet terrace with splendid views of the town and hills and is conveniently located opposite the train station and with a few restaurants nearby.

Day 2: Sintra Palaces | 9 km

Your walking tour takes you to the three most prominent monuments of Sintra: Castelo de Mouro, Palacio da Pena and Palacio Nacional. You start with a steep ascent to the Moorish castle and King Ferdinand’s colourful dream palace, followed by a walk on the vast palace grounds and finally a steep descent via Vila Sasseti to the town centre of Sintra, where the National Palace stands.

  • Walking for the day: 9 km, 4-5 hours, ↑­­­­475 m ↓475 m
  • Overnight in a 2-star hotel (Hotel Nova Sintra or similar)

Day 3: Convento dos Capuchos to Azoia | 12 km

Today you leave the crowds behind with a transfer to the Convento dos Capuchos, a classic example of an austere 16th-century Franciscan monastery that you can visit before starting the walk. Your walking route leads you through mystical Mediterranean woodlands past hillside menhirs and the shrine dedicated to the Virgin Mary of Peninha. Then you descend to Azoia and get the bus back to Sintra.

  • Walking for the day: 12 km, 5 hours, ↑­­­­425 m ↓500 m
  • Overnight in a 2-star hotel (Hotel Nova Sintra or similar)

Day 4: Sintra Manor Houses | 5-7 km

In the 19th and early 20th centuries, a Romantic wind blowing through Europe was strongly felt in Sintra. Within a few square kilometres, you will find extravagant palaces and mansions built by nobles and wealthy merchants, most of which are still occupied or in use as luxury hotels. 

  • Walking for the day: 5/7 km, 2/3 hours + time used for visiting the palaces
  • Overnight in a 2-star hotel (Hotel Nova Sintra or similar)

Day 5: Sintra to Praia Grande | 15 km

Today you leave the wealth and romance of Sintra behind as you walk north through fields, vineyards and pine forests toward the rugged coast. In the pretty fishing village of Azenha do Mar, you pick up the GR-11 and follow it south to the 1970’s hotel on “Praia Grande” in Arribas, with its huge saltwater pool.

  • Walking for the day: 15 km, 5 hours, ↑225 m ↓485 m
  • Overnight in a 3-star hotel (Arribas Sintra Hotel or similar)

Day 6: Praia Grande Circular Walk | 12.5 km

From Hotel Arribas, you take a long-distance walking path, the GR-11 “Costa Atlantica”, going south along fishermen’s trails to reach the village of Ulgueira. Beautiful views of Cabo de Roca – the westernmost point of the European continent – and a nice sandy beach along the way. After a drink or ice cream at Casa Doña Maria in Ulgueira, you return to Praia Grande via a different route which passes through the authentic village of Almoçageme. 

  • Walking for the day: 12.5 km, 4.5-5 hours, ↑575 m ↓575 m
  • Overnight in a 3-star hotel (Arribas Sintra Hotel or similar)

Day 7: Azoia to Guincho and Cascais | 8-17.5 km

Your last day of walking begins with a transfer to Azoia, where you pick up the GR-11 and follow it along the coast to the 17th-century fortress of Fortaleza de Guincho, now a luxury hotel with views over Praia do Guincho. You can stop off part-way (after 8 km and approximately 2.5 to 3 hours walking) and take the bus directly to Cascais or walk an additional 9.5 km all the way to your hotel (footpath between the road and beach).

  • Walking for the day: short option: 8 km, 3 hours, ↑175 m ↓375 m; long option: 17.5 km, 5 hours, ↑275 m ↓475 m
  • Overnight in a 3-star hotel (Hotel Baía or similar)

Day 8: Departure

The tour ends after breakfast. You can extend your stay or return to Lisbon by train (~1 hour).

What to Expect


Accommodation is in charming hotels in double or twin private en-suite rooms. We have carefully hand-picked all places and regularly monitor their quality. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Click to view default hotels

  • Hotel Baíaa family-run hotel located on the seaside, with the Sintra range as a background. With a restaurant and a terrace that offers views to the Sintra bay, near the town centre of the lively Cascais.
  • Arribas Sintra Hotellocated by the sea, in a high-end neighbourhood in Sintra. All rooms have extraordinary views of the sea. Restaurant and a swimming pool.
  • Hotel Nova Sintraa family-owned hotel founded in 1948. It has a large sun terrace overlooking the Sintra Mountain Range and a romantic patio shaded by large trees. It features simply decorated rooms and free Wi-Fi.

*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.


All breakfasts are included. Dinners are available at all overnight accommodations or in the towns. There are possibilities for lunches along the way, or you can buy some food in advance.

Difficulty & terrain

This walk is graded easy to moderate and moderate and includes daily walks of 3-5 hours on average; the terrain is hilly with well kept sometimes stony paths (read more about difficulty grades). The routes are not well waymarked, but we will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. We strongly advise you to follow only marked trails and never shorten the path through the unknown and unmarked terrain. More detailed info on route navigation will be included in your holiday information pack.

When to go

This trip is available throughout the year. Best months to visit are April – June and September – October as in summer months it may become too hot for walking.

The flexibility of self guided holidays means that there are no fixed dates and you can start your trip on any date during the season.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

Our recommended airport for this tour is Lisbon (LIS).

By train or bus
  • There are regular trains between Lisbon and Sintra (journey time ~ 1 hour) and Cascais and Lisbon (journey time ~1 hour).
  • Train schedules can be checked here. For more details use the Omio planner above.



  • 7 nights in a mix of welcoming 2 and 3-star hotels
  • 7 breakfasts
  • Detailed digital route descriptions and maps in English including GPS tracks. Please note that the info pack is emailed to you prior to departure, and no printed documents are mailed or provided on site
  • Luggage transfers from hotel to hotel on day 5 and day 7 (1 piece up to 20 kg per person)
  • Private transfers on day 3 & day 7 in the morning
  • 24/7 phone assistance by our local office/representative


  • Airfare and connecting land transfers
  • Lunches, dinners, drinks and snacks
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Local tourist taxes and entry fees (payable on-site)
  • Any items not explicitly listed as included

Options, extras & supplements

  • A supplement applies to members of a group who require a single room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Extra nights along the trail are bookable upon request
  • Private transfers from/to the airport