Self Guided Walking Holidays & Cycling Holidays

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Self-guided walking holiday Lisbon & Sintra Short Break


  • 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
  • Stay in the lovingly restored 13th century Convent of Sâo Saturnino
  • 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.

Day 1: Arrive in Lisbon and overnight

The captivating capital city of Portugal is one of those cities you are sure to fall instantly in love with as you wander the old cobbled streets of the Alfama neighbourhood.  Dine out on delicious street food at the famous Time Out food market, climb to the top of the city’s famous “seven hills” for panoramic views, or visit the Castelo de Sao Jorge (St George’s Castle), with its amazing views over the Tegus River.

Overnight: Lisbon

Day 2: Sintra Palaces and Monuments Loop Walk

Enjoy a delicious pastel del nata and galao (milky coffee) for breakfast before either jumping on an early train to Sintra or if you prefer, spend the morning in Lisbon to further explore the city and take a train later on in the day. With the train ride only being 40 minutes and this afternoon’s walking being a short one, there is plenty of time to discover the extravagant palaces, manor houses and castle of Sintra.

First stop is the Quinta Regaleira, a lavish mansion and former home to Portuguese nobility. With it’s enchanting, tropical gardens and lots of hidden caves, tunnels and wells, you can easily spend a couple of hours here. Continue on foot, following a peaceful wooded trail uphill to the Pena Palace, with its impressive multi-coloured turrets, dramatic architecture and exotic gardens. Finally, visit the amazing Castel dos Mouros (Moors Castle) which sits right on top of the hill and offers amazing views over Sintra. Head back to the centre of Sintra via a tranquil stepped forest path.

Please note that entrance fees to the above are not included to keep your day flexible, and we recommend booking in advance to avoid the sometimes long entrance queues. It is worth noting that during the autumn and winter months from October through to March, the monuments close at 5pm.

Walk: 7km

Elevation gain/loss: +270m/-240m

Overnight: Sintra

Day 3: Loop Walk to Capuchos Convent and Peninha Chapel

After a short transfer into the heart of the Sintra-Cascais Natural Park (30min), a lovely loop walk today takes you into the heart of the Sintra forest and “Moon Hills” (so called because the ancient Celts worshipped their moon god here). First stop is the one of the highest points in the area where you will find the hill-top Peninha Chapel with far-reaching views across the countryside. Dedicated to Our Lady of the Rock, it is said that in the past sailor’s wives would come here to keep watch for the return of loved ones.

Continue through the forest to the remarkable Capuchos Convent, also known as the “Cork Convent”, because of its cork-lined tiny cells. Spend some time exploring the warren of ruins, where monks previously lived a simple life in this idyllic location. Overnight tonight in the romantic São Saturnino Convent, lovingly restored from 13th century ruins. Your stay at this hotel with its labyrinthine interior and tranquil setting in a hidden valley is sure to be a unique and very memorable experience.

Walk: 16km

Elevation gain/loss: +540m/-540m

Overnight: Azoia

Day 4: Walk to Cascais

Leave Azoia and the “Serra da Sintra” this morning and head to the rugged coastline following winding paths on the GR11 to the 17th century fortress “Fortaleza de Guincho” (now a hotel). From here, it is a very easy walk following a path between the road and the ocean passing lighthouses and interesting cliff formations to reach Cascais. If you prefer, you can take a bus straight to Cascais from Guincho which shortens the day by 9km.

Enjoy an evening in the much-loved seaside town of Cascais with its trio of beautiful bays. Wander through its pedestrianized old town and along the marina before eating alfresco in one of the many local seafood restaurants, perhaps sampling some of the tasty fresh Bacalhau (cod). 

Walk: 18km

Elevation gain/loss: +145m/-325m

Overnight: Cascais

Day 5: Onward journey

Check out after breakfast and make your way by train back to Lisbon for onward travel connections (40 min)


3 Nights in boutique hotels and guesthouses and 1 night in the Sao Saturninho Convent are included.

We regularly use the following properties but may accommodate you elsewhere if these are not available. However, they will be of a similar standard.

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




Quinta Colina - Lisbon

Quinta Colina

A boutique guesthouse in an historic 18th century building, located in the peaceful Pena area, one of Lisbon’s famous Seven Hills. Quinta Colina retains the classic beauty of the building and complements it with unique and modern rooms. Just a short walk away from Rossio Square, it is in the perfect location for exploring the city.




Aguamel Sintra

Aguamel Sintra

A family run boutique guest house in the heart of Sintra, set in a beautiful building dating back to 1885. The bedrooms are tastefully decorated, combining local antiques with modern touches. Enjoy special touches like a lovely refreshing drink on arrival and help yourself to homemade cake as well as the most delicious breakfasts!




São Saturnino Convent

São Saturnino Convent

Originally built in the 13th century, the Convento has been lovingly restored from ancient ruins into an elegant hotel. With its labyrinthine interior and tranquil setting between the hills and the sea, your 3-night stay here will be a unique and unforgettable experience. Each room has open beams, antique furniture and its own special charm. The pool has superb views south to the sea and over the majestic Touro Valley.




Pergola House

Pergola House

Typical of traditional Cascais architecture, Pergola House with its beautiful façade and colourful gardens offers a very warm welcome and fantastic hospitality including a complimentary glass of Port every evening.


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.

Single Rooms & Solo Walkers

This trip is available to solo walkers, although there is a supplement due to the fact that some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.

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 270m and 540m.

Navigation, Route Notes & Maps

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!

Baggage Transfer

Your bags will be transferred 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.

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

General Information

The distances and ascents/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example. proper rain gear, sun hat, sunscreen. Your information pack has detailed advice and a kit list on what to take.This includes good waterproof gear, walking shoes/boots, and lots of other useful bits and bobs.

Getting to Lisbon

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 Cascais

Again, 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).


  • 3 Nights in boutique hotels and guesthouses
  • 1 Night in the Sao Saturninho Convent
  • 4 Breakfasts
  • Baggage transfers
  • Transfers as per itinerary
  • Information Pack
  • Maps, route notes, GPX tracks and access to our smartphone app
  • 24-7 emergency telephone support


  • Travel insurance (required)
  • Travel to Lisbon and from Cascais
  • Train travel between Lisbon and Sintra
  • Lunches and Dinners
  • Drinks and snacks
  • Personal equipment
  • Entrance Fees


  • Single room supplement(s) if applicable
  • Solo walker supplement if applicable
  • Additional nights before, during and after the walk

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as Portugal is extremely popular and the accommodations get booked up quickly.

How fit do I need to be?

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 270m and 540m.

How do the baggage transfers work?

Your bags will be transferred 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.

What equipment do I need?

Your detailed information pack will be sent to you after you book. This has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.

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lf you require more information before booking, please contact us on

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Macs Adventure - Head Office: Skypark 5, 45 Finnieston Street, Glasgow, G3 8JU, UK


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