Peace of Mind Guarantee: Worry-free booking after Covid-19 >Where can I travel? Advice on planning >


Walking Sintra to Cascais

7 Days & 6 Nights
  • 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
  • Stay in the lovingly restored 13th century Convent of Sâo Saturnino
  • 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 impressive “cork convent” of Capuchos, and the remote Peninha Chapel. Feast on delicious fresh seafood and Colares wine, whilst sipping local Colares wine, and stay overnight in boutique hotels, including the wonderful Convent of Sâo Saturnino.
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 guesthouse including a wonderful convent, lovingly restored from 13th century buildings. Perfect for those who like to mix their walking with lots of historical and cultural highlights.

Tour Style:

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


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


Most Popular

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

Activity Level & 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 270m and 540m. On Day 5 you will walk along clifftop coastal paths which can feel exposed so if you suffer from vertigo, you may wish to miss this day’s walk.


The route is way-marked in places and not in others. However, we will provide you with detailed turn-by-turn route notes and maps so you will have no problem finding your way. 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.


Your holiday includes accommodation in boutique hotels, guesthouses and the Sao Saturninho Convent.

You can add on extra nights in any of the overnight locations. We also offer an upgrade to the Lawrence's Hotel in Sintra. Please select this as part of the booking if you would like this option.

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 the São Saturnino Convent
  • Breakfast at each accommodation.
  • Door-to-door baggage transfer as per itinerary.
  • Transfers as per itinerary.
  • Detailed Information Pack.
  • Maps, route notes, GPX tracks and access to our smartphone app.
  • 24/7 telephone support from our UK office.
  • Travel insurance (required)
  • Transport to the start or from the finish of the walk
  • 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).

Luggage 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

The reviews for this tour up until November 2019, are based on a previous itinerary. As of November 2019, minor changes and improvements have been made. The routes were all re-checked and route notes re-written in 2019 to alleviate problems with GPS and routefinding. And an additional night has been included at Sao Saturnino Convent as this appears to be a real highlight for many of our customers!

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.

How far in advance do I need to book?
What equipment do I need?


Day 1 Arrive Sintra Day 2 Sintra Palaces and Monuments Loop Walk 3.25 miles / 5.2 km Day 3 Transfer to Monserrate Palace, walk to Praia Grande 7 miles / 11.2 km Day 4 Walk to Azoia 9.75 miles / 15.6 km Day 5 Loop walk from Azoia 7.6 miles / 12.2 km Day 6 Walk to Cascais 11 miles / 18 km Day 7 Onward Travel

The Macs Way

  • Custom-made Adventures Custom-made Adventures
  • Freedom Freedom
  • Book with Confidence Book with Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Build your perfect adventure your way
  • Flexible itineraries built around you
  • Knowledgeable and helpful specialist trip planners
  • Customize your trip to suit your interests
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation comfort levels
  • Choice of trip styles
Authentic adventure travel experiences on your own terms
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time
  • 14,000+ unbiased trip & service reviews
  • Feefo Gold Award 2019
  • 25,000+ travelers trust us each year
  • As featured in the Guardian, Times, Nat Geo Traveler
  • Founder owned & operated since 2003
  • 100+ passionate team members across the US, UK & Europe
You can be confident that every detail of your journey has been expertly planned
  • Carefully planned adventures
  • Quality, hand-picked accommodations
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way and make a positive impact
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimize your impact
  • Maximize the benefit of your travel
  • Challenge yourself & grow

Blog Articles

$ - USD - US Dollar
Country/Region name: