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Lisbon & Sintra Short Break

5 Days & 4 Nights 3.7 Read 3 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 moon hills of Sintra
  • 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 before overnighting in the tiny little village of Azoia. Finish in Cascais, a much-loved seaside town filled with al fresco seafood restaurants, and tiny winding alleyways.
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What To Expect

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.

Trip Type:

Slower Adventures | Slower Adventures


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

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: 12 Years

Ideal if you have an interest in:

  • Short Break
  • Coastal Walking

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 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

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, 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 and from Cascais
  • Lunches, 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.

Time of Year

Sintra offers great weather most of the year round but the months of July and August can get very hot, and can make it uncomfortable to walk. 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 (Sintra) are always slightly cooler than Cascais and Lisbon due to the higher elevations, but please note that it could get hot in Lisbon and Cascais during the summer months, with the higher risk of wild forest fires throughout Portugal.

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).

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.

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Day 1 Arrive Lisbon Day 2 Transfer to Sintra, Sintra Palaces and Monuments Loop Walk 3.25 miles / 5.2 km Day 3 Transfer to Capuchos Convent, Walk to Azoia 8.75 miles / 14 km Day 4 Walk to Cascais 10 miles / 16 km Day 5 Onward Travel

  • Sintra to Cascais

    This self-guided walking holiday takes you through the Sintra Cascais Natural Park, following beautiful and rugged coastal paths and inland trails with stops to explore the exquisite palaces, castles and monasteries of this stunning part of Portugal.

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