Self Guided Walking Holidays & Cycling Holidays

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Self-guided walking holiday Walking Sintra to Cascais


  • 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.

Day 1: Arrive in Sintra and overnight

The UNESCO World Heritage site of Sintra is just a 40min direct train ride away from nearby Lisbon. Stroll around the historic centre, soaking up the atmosphere of this wonderfully vibrant, colourful town and perhaps visit the Palacio Nacional de Sintra, a Gothic palace featuring ornately painted ceilings. In the evening, sit back, relax and enjoy dinner in one of the many cosy restaurants serving delicious Portuguese specialities such as the tasty Bacelhau a bras cod dish.

Overnight: Sintra

Day 2: Sintra Palaces and Monuments Loop Walk

Today is dedicated to discovering 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.

Walk: 5.2km

Elevation gain/loss: +/-219m

Overnight: Sintra

Day 3: Walk to Colares, transfer to Azoia

Leaving Sintra, follow forest trails into the Sintra hills, stopping off to visit the fantastic Monserrate Palace, a Neo-Gothic mansion set within landscaped gardens. Take your time to explore the gardens which were built by a series of wealthy British merchants and artists.

Continue to Colares, a unique wine region  where the vineyards grow across the sand and produce delicious red and white wines from the ramisco or malvasia grapes.  In the village of Colares itself, you may like to visit the Colares Regional Winery, founded in 1931, and the oldest co-operative winery in Portugal.

A pre-arranged transfer will take you from Colares to Azoia late this afternoon, where you can check into 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: 11.2km

Elevation gain/loss: +320m/-508m

Overnight: Azoia

Day 4: Loop Walk to Capuchos Convent and Peninha Chapel

A 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. Descend to the little village of Pe da Serra, where you may like to enjoy a late lunch before returning to Azoia.

Walk: 15.6km

Elevation gain/loss: +511m/-513m

Overnight: Azoia

Day 5: Loop walk to Praia Adraga

Head to the rugged Atlantic coast, and enjoy a walk to Praia Adraga. Leaving Azoia you soon reach Cabo da Roca, Europe’s most westernmost point and once considered to be the edge of the world.

Continue walking on clifftop paths accompanied by views over the blue ocean and wind your way down to the beautiful golden beaches of Ursa and Adraga. Stop for lunch at the beachside restaurant and then turn inland,  passing through a pine forest and the traditional village of Ulgueira before heading back to Azoia.

Walk: 12.2km

Elevation gain/loss: +412m/-411m

Overnight: Azoia

Day 6: Walk to Cascais

Leave Azoia and the “Serra da Sintra” this morning and return to the rugged coastline following winding paths on the GR11 to the 17th century fort “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.

Walk: 9-17.5km

Elevation gain/loss: +113m/-310m

Overnight: Cascais

Day 7: Free day in Cascais

You have a full day to explore and enjoy the delightful 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).  In the evening there is also a very good bar, where musicians perform traditional fado music which is incredibly haunting (worth booking in advance if this is your cup of tea!)

Overnight: Cascais

Day 8: Onward journey

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


4 Nights in boutique hotels and guesthouses and 3 nights 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.




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, forest and clifftop paths and daily ascents are between 113m and 511m. 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. There is also some rocky terrain occasionally which can be slippy when wet.

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 Sintra

Sintra is most easily accessed from Lisbon Airport. Simply hop on the airport bus to Entrecampos station (10min) then it is a 40min direct train journey to Sintra.

Please check the Comboios de Portugal website for timetable planning.

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).


  • 7 Nights in boutique hotels and guesthouses
  • 7 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 Sintra and from Cascais
  • 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, 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.  

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

+44 (0)141 530 5464

+1 -844-858-0740


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