We noticed that you are based in the United States - click here to visit our USA website. US 

Walking Sintra to Cascais

7 Days & 6 Nights 4.6 Read 9 reviews
  • Walk from the wooded hills to the rugged coastline in the Sintra-Cascais Natural Park
  • Explore the colourful monuments of the UNESCO World Heritage Site of Sintra
  • Cabo da Roca lighthouse, the westernmost point of mainland Europe
  • Discover the atmospheric "moon hills" of Sintra and hilltop Peninha Chapel
  • Delicious fresh seafood as you finish in the lovely seaside town of Cascais
Walk through the Sintra-Cascais Natural Park, from inland wooded trails to the rugged Atlantic coast, with views over golden sandy beaches before finishing at the seaside town of Cascais. Explore the UNESCO World Heritage Site of Sintra, renowned for its exquisite palaces, castles, monasteries and lush tropical gardens. Easily accessible from nearby Lisbon, it is clear to see why it was a popular sanctuary for Portuguese nobility between the 15th and 19th centuries. Feast on fresh seafood and Colares wine along the way, whilst staying overnight in boutique hotels and charming quinta-style guesthouses, where you'll receive a warm Portuguese welcome.

What To Expect

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

Trip Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.


Multi Centre Walking | With a mix of loop and point-to-point walks stay 2 or 3 nights in one place which offers the chance to slow down and really explore a destination.

This trip is suitable for:

Solo Travellers

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

Ideal if you have an interest in:

  • Foodie
  • Wine
  • Coastal Walking

Grade & Terrain

This trip is graded ‘moderate’ overall and includes daily walks of 10-16km. It is suitable for most people that are in good physical fitness. The route follows a mixture of gravel trails, sandy coastal trails, forest and clifftop paths and daily ascents are between 200m and 500m. On Day 4 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 terrain can also be quite challenging here, with steep sections of bare dirt. You may wish to use walking poles here. We recommend training ahead of this tour, by walking some daily walks of similar daily distances to your planned itinerary.


As the navigation on this tour is fairly straightforward, it does not have turn-by-turn directions. It will be necessary to use the Macs Adventure Smartphone App. Simply download the app for offline use and follow the route on your phone with the assurance that you will be able to find your way, even without turn-by-turn directions. The route is way-marked in places and not in others. Several trails have way-marks on the ground, so please do keep your eye out for these. You will receive a digital booklet one month prior to your arrival with information about these, including a description of the route and points of interest. Using the two elements alongside each other should go a long way to ensure you have a safe, enjoyable and problem free day.

Accommodation Information

Your holiday includes accommodation in charming 3 and 4* hotels and quinta-style guesthouses, where the warmest of welcomes and traditional hospitality will make your stay extra special. All rooms are comfortable and have a private bathroom. 

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.

  • 6 nights in boutique hotels and charming guesthouses
  • Breakfast at each accommodation
  • Door-to-door baggage transfer as per itinerary
  • Transfers as per itinerary and arrival transfer from Lisbon to Sintra
  • 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 before the start, and from Cascais on the final day
  • Lunches and Dinners
  • Drinks and snacks
  • Personal equipment
  • Entrance Fees
  • Additional nights before, during and after the walk
  • Transfer from Cascais to the airport on the final day

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. 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. Both spring and autumn offer excellent conditions for walking. Average temperatures 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

Transfers are not included on the final day. It is very easy to get between Cascais and Lisbon Airport by public transport. You can 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 transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation, giving you the freedom to walk each day with just a day pack. We ask you to limit your luggage to one bag of up to 20kg per person. Please ensure that you do not bring more than one bag of 20kg as if this occurs, you may be asked to pay an additional fee for an extra bag.

At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase.  Your booking includes transfer of 1 bag per person.  It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.

General Information

The distances and ascents/descents are approximations of the recommended routes. 


Please be prepared by packing all necessary items. 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?
What happens if I can't walk a stage?
How fit do I need to be?
When is the best time of year?


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 9 miles / 14.5 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

Blog Articles

You May Also Like

  • 5 Days 4 Nights
    Lisbon & Sintra Short Break
    Combine vibrant Lisbon with the beautiful coast and hills of the Sintra-Cascais Natural Park.
    • The vibrant city of Lisbon.
    • Colourful UNESCO World Heritage Site of Sintra.
    • The seaside town of Cascais.
    From £510.00
  • 7 Days 6 Nights
    Algarve Coastal Trails
    Walk the Algarve Coast from Lagos to Cabo de Sao Vicente, Portugal's most southwest point.
    • Walk quiet coastal trails through the Algarve
    • Fresh Atlantic air at Cabo de Sao Vicente
    • Local food and wine at the many beach bars
    From £790.00
  • 8 Days 7 Nights
    Porto & the Douro Valley
    Explore vibrant Porto and walk through the golden rolling hills of the Douro River Valley.
    • Discover Porto, a UNESCO World Heritage Site.
    • Enjoy tastings at local wineries.
    • A scenic river cruise down the Douro River.
    From £990.00

The Macs Adventure Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book With Confidence Book With Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our knowledge and expertise, to suit you.
  • Knowledgeable and helpful friendly specialist adventure planners
  • Wide variety of trips to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation options
  • 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.
  • 18,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2023
  • As featured in the Guardian, National Geographic Traveller, and more
  • Founder owned & operated since 2003
  • Passionate team members based in the US, the UK & Europe
  • 100% Financial Protection
You can be confident that every detail of your holiday has been expertly planned.
  • Meticulously planned adventures
  • Quality, hand-picked accommodation
  • 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
  • Minimise your impact
  • Maximise the benefit of your travel
  • Challenge yourself & grow
£ - GBP - Pound
Country/Region name: