Cascais Sintra Walking Holiday

With easy access from Lisbon, Sintra-Cascais Natural Park is the region for this beautiful Cascais Sintra Walking Holidayhiking tour.

The Cascais Sintra Walking Holiday starts in the beautiful coastal town of Cascai following the dramatic coastline, passing wide bays of golden sand and rugged cliffs until you reach the Westernmost point of Europe – Cape Roca. Hike inland towards the forest and follow a succession of hilltops capped by luxurious vegetation. Explore Sintra and its incredible architectural heritage and history. During the route, take the opportunity to visit unique Convent’s, Palaces and Castles discovering the most interesting landmarks of the region.

Suitable all year round, including the summer as it’s not too hot due to the NW winds from the Atlantic. Also possible to Hike during winter but with a higher possibility of rain from November to February.

Highlights Cascais Sintra Walking Holiday

  • Stunning coastal Hiking
  • Unique cultural and historical sights
  • Pena National Palace
  • Capuchos, an impressive capuchin Covent
  • Mouros Castle and it’s view over Sintra
  • Sintra UNESCO World Heritage
  • Cascais, a beautiful city by the sea
  • Charmingandhistoricalhotels
  • Traditional food and fresh fish from the Atlantic Coast
  • Roca Cape, the westernmost point of Europe

Type Inland/Coastal Hiking Tour. Self-guided
Season All year round. Summers not too hot because of the NW winds from then Atlantic. Also possible to Hike during winter but with a higher possibility of rain from November to February. Any date subject to hotel availability.
Duration 8 days 7 nights. 6 days hiking
Accommodation 7 nights (2 nights on a 5* Hotel. 1 night 4* Hotel; 2 nights on a Charming Hotel on a Convent; 2 nights on a Guest House).
Begin Cascais (Lisbon region)
End Sintra (Lisbon region)
Difficulty level Easy to moderate
Distance 74km. Average of 12km per day
Getting There Fly to Lisbon. Private airport transfers included in price.

What we do

We put together the trip for you: reserve the hotels, transfer the luggage and organise your transfers to the start of your itineraries. Each tour includes a complete Road book with detailed itineraries, information for visits along the way, a detailed map and total peace of mind with our 24-hour local support.

We work with local operators through-out each destination that are passionate about their regions.

We can tailor make this tour, if you want to add an extra rest day, spend a few days relaxing before or after the trip just let us know and we will be happy to provide a quotation.

Transfer from Lisbon airport to Cascais (00h30min)
Depending on arrival time explore the delightful town of Cascais and its bay. Walk around by the pedestrian streets and find a nice restaurant to have dinner.


Hotel Vila Galé Cascais

Small transfer to Guincho beach (10min) where you hike will start. This day is short so in the beginning you can walk around a impressive dune close to the beach by some wooden pathways. You will cross the famous Guincho beach usually full of surfers and Kite-surfers! Your route will follow the rugged coast line by a coastal path, to reach the São Saturnino Convent at the head of a secluded valley. This is a recovered Convent which was reconstructed from several old ruins; in the past this was a sacred place honoring St Saturnino

Coastal hike day: 9km, +400m
LODGING: Charming Hotel on a Covent

Day 3: AZÓIA
On this day you will do a circular walk that will take you into the ‘Moon Hills’ – as Sintra Hills are known! This route goes up to one of the highest points in this hills where you will find a hill-top chapel at Peninha. Incredible scenery from the top!
The route will descend by other trails with great views over the Ocean returning to your Hotel
LODGING: Charming Hotel on a Covent
HIKE: Inland hike day: 10km, +300m

Return to the trails by the coast, and admire beautiful scenery over the cliffs with the ocean stretching as far as your eye can see. You will reach Cape Roca, Europe’s westernmost point, a wild and rocky promontory once thought to be the edge of the world. Continue on the cliffs passing by a wild and beautiful beach named Ursa! Then pass by the beautiful Adraga beach – there’s a great restaurant for lunch here! Turn inland passing a nice pine forest and discover the typical village of Almocageme. Soon you get to Colares Village, where you will stay two nights at a guest house on the hills of Sintra.

Lodging: Sarrozal House
HIKE: Coastal hike day: 13km, +500m

On this day you will do a circular walk that takes you into the heart of Sintra forest and hills. During today hike time to visit the remarkable Capuchos Convent, also called Cork Convent, because its miniscule cells lined with cork. Visiting Capuchos is an incredible experience as you squeeze through to explore the warren of cells, chapels, kitchen and cavern. The monks lived a simple, touchingly well-ordered life in this idyllic yet spartan place. The convent was constructed according to the philosophy of respecting harmony between humans and divine construction; that’s why the convent blends with the nature including in its structure enormous granitic rocks.
Continue the route going down to the typical village of Colares where you can lunch on a typical restaurant or try a wine tasting at Colares Winery.

Lodging: Sarrozal House
HIKE: Inland hike day: 15km, +500m

Today is a gorgeous day – you will arrive to Sintra, the highlight of your holiday! Hike on forest trails on the hills till you reach to the impressive Monserrate Palace, a Neo-Gothic mansion set within fine landscaped gardens. It’s not a long walk today so there is ample time to explore the house and gardens. Developed by a series of wealthy British merchants, artists and industrialists over many years, the house today is a remarkable place, boasting ornate interiors and extensive gardens which include the first lawn planted in Portugal, a wonderful collection of ferns and a number of intriguing follies. Continue to Sintra, where you spend your last two nights at a historical 5* Hotel from the XVIII century.

Lodging: Boutique Hotel
HIKE: Coastal hike day: 13km, +500m

This is a gorgeous day exploring the hills above Sintra Village, passing by castles and palaces and old manor houses! Such is the grandeur and importance of these buildings and monuments that the ‘Cultural Landscape of Sintra was designated a UNESCO World Heritage Site in 1995.
During your day hike you will pass by two of the most important monuments of Sintra with time to visit. First the amazing Moorish castle…Then the fabulous Pena National Palace high on a hilltop above Sintra. With impressive multi-colored turrets, Pena’s dramatic architecture has landed it on the UNESCO World Heritage sites list and made it one of the Seven Wonders of Portugal. Time to visit the palace and its exotic and luxuriant gardens. Inside the gardens access to the highest point of Sintra hills (Cruz Alta) with a magnificent view. Return to the village and when the day is done, indulge in one last exquisite dinner, relaxing in the elegance of sumptuous Sintra!

Lodging: Boutique Hotel
HIKE: Inland hike day: 9km + 5km, +450m

Transfer from to Lisbon Airport (0h30)

Individual room supplement €405
01.01. – 26.03.
01.11. – 23.12.

Individual room supplement €459
27.03. – 26.05.
27.09. – 31.10.

Individual room supplement €509
(easter week) 14.04. – 20.04.
27.05. – 26.06.
30.08. – 26.09.

Individual room supplement €519
27.06. – 29.08.


Additional supplement applies if you are travelling solo. Please contact is for supplement price.

You can add extra days/nights at accommodations along the way if you wish to explore a particular location a little longer.

Sintra is an incredible place with a lot of amazing historical sites to visit. Amongst them, we strongly recommend you to visit Quinta da Regaleira, one of the most surprising estates in Sintra. Located at the outskirts of the town, it was built in 1904-1910, in the last days of Portuguese monarchy

  • Detailed information about tour, including maps and GPS track;
  • Detailed route descriptions and pre departure information pack;
  • GPS for navigation;
  • Luggage Transfer from Hotels every day during tour;
  • Telephone (free to call us 24h. per day)
  • Lisbon Airport transport to first Hotel and briefing about tour;
  • Transfer from last hotel to Lisbon;
  • 7 nights lodging in superior accommodation in double / twin room. Breakfast included.

Your Accommodation

7 nights lodging on Charming accommodations on BB basis
(Vila Gale Cascais 4*,
S.Saturnino Guest House,
Sarrazola House Superior rooms,
Sintra Boutique Hotel4 *)

Where you rest your head after an active day is hugely important to us. We go to great lengths to find properties that are unique expressions of the region you are travelling through. Think of them as the charming and intimate garnish atop your trip. 

Whether nestled in the heart of a village or lost in the countryside and surrounded by nature, all accommodations are chosen using a strict criteria of comforthospitality, and authentic charm. We like to use locally run independent small hotels, guest houses and B&Bs instead of the larger “chain” hotels.  All of them are hand-picked, visited, and re-visited by our local partners. On most of our holidays you will be staying in different hotels and their  uniqueness and individual character only adds to the enjoyment of your holiday. You will also benifit with knowledge that your trip is contributing to local economies, and supporting local family run businesses.

You will be welcomed in a double or twin room (2 beds) – based on double occupancy.
All of our rooms have private bathrooms.
Individual rooms are possible upon request when you book; they are subject to availability and incur a supplemental fee.
For biking trips, all of our inns have a safe place to keep bicycles for the night

Fly to Lisbon. Lisbon Airport transport to first Hotel . Transfer from last hotel to Lisbon;

Flights are not included in the price. Adventure Holidays do not book flights. We will  advise you on best times, dates and airfares to book.



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