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Lisbon & Sintra Short Break

5 Days & 4 Nights 4 Read 1 reviews
  • Combine vibrant Lisbon and the Sintra-Cascais Natural Park on a short break
  • Explore the colourful monuments of the UNESCO World Heritage Site of Sintra
  • Discover the enchanting Capuchos Convent and beautiful hilltop chapel of Peninha
  • Walk the rugged coastline between Azoia and Cascais
  • Finish in the lovely seaside town of Cascais, and feast on some delicious seafood
Combine the captivating capital city of Portugal, Lisbon, with the beautiful coast, lush forests and hills of the Sintra Cascais Natural Park on this short walking break. The city of Lisbon, and its famous “seven hills” is bursting with cultural heritage and amazing dining experiences from the famed Time Out street food market to classy restaurants serving a multitude of fresh seafood dishes. Just a short hop on the train brings you to Sintra, a UNESCO World Heritage Site filled with tropical gardens and colourful palaces and monuments. Explore the lush green forest of the “Sintra Moon Hills” , enjoy views over golden sandy beaches and discover the impressive “cork convent” of Capuchos and the remote Peninha chapel. Finish in Cascais, a much-loved seaside town al fresco seafood restaurants, and tiny winding alleyways.
Perfect if you are short of time and would perhaps like to extend or combine a trip to Lisbon with some beautiful walking. Follow a variety of paved trails, clifftop paths and forest trails. There are some significant elevations gains in the Sintra hills, but nothing too challenging. You will stay overnight in boutique hotels and guesthouses.

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


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 and forest paths and daily ascents are between 210m and 500m.



The route is way-marked in places and not in others. You will receive a booklet including a brief 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

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 and quinta-style guesthouses.

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 guesthouses.
  • 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)
  • Travel to Lisbon and from Cascais
  • Train travel between Lisbon and Sintra
  • Lunches, 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.

By Rail: If you are travelling to Lisbon from elsewhere in Portugal or Spain, it is also easily accessed by rail. A train from Porto to Lisbon takes 3 hours. 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.

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Day 1 Arrive Lisbon Day 2 Transfer to Sintra, Sintra Palaces and Monuments Loop Walk 8.75 miles / 14 km Day 3 Transfer to Capuchos Convent, Walk to Azoia 6.25 miles / 10 km Day 4 Walk to Cascais 11 miles / 18 km Day 5 Onward Travel

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