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Walking Sintra to Cascais

7 Days & 6 Nights 4.7 Read 6 reviews
  • Follow trails through the hills and coastline of the Sintra-Cascais Natural Park
  • Explore the colourful monuments of the UNESCO World Heritage Site of Sintra
  • Breathe in the fresh sea air as you walk above the wild Atlantic coast
  • Discover the atmospheric "moon hills" of Sintra and hilltop Peninha Chapel
  • Feast on delicious fresh seafood as you finish in the lovely seaside town of Cascais
Walk through the Sintra Cascais Natural Park, following beautiful coastal and inland trails and exploring the exquisite palaces, castles and monasteries of this stunning part of Portugal. Easily accessible from nearby Lisbon, the UNESCO World Heritage Site of Sintra is a sight to behold. With its lush tropical gardens and colourful monuments it is clear to see why it was a popular summer residence for Portuguese nobility between the 15th and 19th centuries. Contrasting trails take you from tranquil wooded hills to the rugged Atlantic coast, with views over golden sandy beaches. Discover the atmospheric "moon hills" of Sintra, and the remote Peninha Chapel. Feast on delicious fresh seafood and Colares wine, and stay overnight in boutique hotels and charming quinta-style guesthouses where you will receive a warm Portuguese welcome.

What To Expect

Easily accessible from Lisbon, this tour offers moderately graded trails through a variety of coastal and inland landscapes on a mixture of paved and forest trails, clifftop paths and quiet country paths. There are some significant elevations gains in the Sintra hills, but nothing too challenging. Stay overnight in boutique hotels and guesthouses. Perfect for those who like to mix their walking with lots of historical and cultural highlights.

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Multi Centre Walking | You will spend multiple nights in one or more of the locations on this walking holiday


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As a guide, we would suggest that the minimum age of traveller this holiday would be suitable for is: 10 Years

Grade & Terrain

This trip is graded ‘moderate’ overall and you should be in good physical fitness to fully enjoy the walking on this tour. The route follows a mixture of gravel trails, forest and clifftop paths and daily ascents are between 150m and 500m. On Day 4 you will walk along clifftop paths which can feel exposed, so may not be suitable if you suffer from vertigo. 


The route is way-marked in places and not in others. You will receive a booklet including a description of the route, a small pdf of the map and points of interest. For navigation, you will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone's GPS so you will have no problems finding the way. You can simply download the GPX tracks to your phone for offline use and off you go! 

Experience & Fitness

This route is suitable for most regular walkers of average fitness. You should train by walking some daily walks of similar daily distances to your planned itinerary.

Accommodation Information

Your holiday includes accommodation in charming 3 and 4* hotels and quinta-style guesthouses.

You can add on extra nights in any of the overnight locations. 

Single Rooms & Solo Walkers

If you require single rooms we would be happy to accommodate you although there is a single room supplement payable. We also welcome solo walkers on this tour, again a supplement is payable.


A breakfast will be provided by your accommodation every morning. These usually consist of a selection of ham and cheeses, as well as some small pastries including the delicious “pastel de nata”, all accompanied by a cup of Galao (milky coffee). Dinners are not included, however there are options to dine out in all of the towns and villages. The food in Portugal is fantastic, famous for it’s codfish dish Bacelhau a bras amongst many other fresh seafood dishes, and the Sintra region in particular is home to the delicious pastry treat, Queijada de Sintra as well as the mouth-watering Colares wine.

Lunch is not included, but you can find small stores in which to purchase items for a picnic lunch, or some of your accommodations can make a picnic lunch if you ask in advance. In your route notes we give advice on where you can eat/pick up lunch.

  • Overnights in boutique hotels and guesthouses
  • Breakfast at each accommodation.
  • Door-to-door baggage transfer as per itinerary.
  • Transfers as per itinerary.
  • Detailed Information Pack.
  • GPX tracks and access to our smartphone app.
  • 24/7 telephone support from our UK office.
  • Travel insurance (required)
  • Travel to Lisbon or from Cascais
  • Lunches and Dinners
  • Drinks and snacks
  • Personal equipment
  • Entrance Fees
  • Additional nights before, during and after the walk

When To Go


You can start this walking tour on any day of the week from January through to June, and from September through to December, subject to availability.

Time of Year

Sintra offers great weather most of the year round but we do not offer this tour in the months of July and August as it can get very hot then, and doesn't make for enjoyable walking. Average temperatures the rest of the year range from 10-15°C (70°F) in the winter to 25-30 °C (77 °F) in the summer months. The inland regions are always slightly cooler than Cascais due to the higher elevations.

Weather and Climate

Sintra offers great weather most of the year round but we do not offer this tour in the months of July and August as it can get very hot then, and doesn't make for enjoyable walking. Average temperatures the rest of the year range from 10-15°C (70°F) in the winter to 25-30 °C (77 °F) in the summer months. The inland regions are always slightly cooler than Cascais due to the higher elevations.

Getting to the Start

Lisbon Airport is easily accessed by direct flights from across the UK, Europe and several cities in the US. Major airlines who fly there include American Airlines, TAP, British Airways, Easyjet and Ryanair amongst others.

If you are travelling to Lisbon from elsewhere in Portugal or Spain, it is also easily accessed by rail. View rail timetables at the Comboios de Portugal website.  

Getting from the End

It is very easy to get between Cascais and Lisbon Airport. Take the train to Casa do Sodre station in Lisbon (40min) and then catch the bus to the airport (20min).

Baggage Transfer

Your bags will be collected from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

General Information

Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

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Day 1 Arrive Sintra Day 2 Sintra Palaces and Monuments Loop Walk 6 miles / 10 km Day 3 Transfer to Monserrate Palace, walk to Praia Grande 8.75 miles / 14 km Day 4 Walk to Azoia 8 miles / 13 km Day 5 Loop walk from Azoia 6 miles / 10 km Day 6 Walk to Cascais 10 miles / 16 km Day 7 Onward Travel

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