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
- Walk the rugged coastline between Azoia and Cascais
- Finish in the lovely seaside town of Cascais, and feast on some delicious seafood
Gallery
Itinerary
Day 1 Arrive LisbonThe 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.

Marquês Pombal Hotel is located in Lisbon with exception adesign, excellent service and modern rooms. Free Wi-Fi, 24-hour reception, a restaurant and bar are all available on site.
A scenic transfer (duration: 45min) will bring you from Lisbon to Sintra this morning. On arrival in Sintra, drop off your luggage at your accommodation then the rest of the day is dedicated to discovering the extravagant palaces, manor houses, and castle of Sintra. The first stop is the amazing Castel dos Mouros (Moors Castle), which sits right atop the hill and offers amazing views over Sintra.
Continue on foot, following a peaceful wooded trail uphill to the Pena Palace, with its impressive multi-colored turrets, dramatic architecture, and exotic gardens. If you have time we also recommend visiting the Quinta Regaleira, a lavish mansion and former home to Portuguese nobility. With its enchanting, tropical gardens and many hidden caves, tunnels, and wells, you can easily spend a few hours here.
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. The distance detailed is also only to the entrance gates of the attractions - you will actually walk quite a bit further by the time you have walked around all of them! A shorter 6km loop is therefore available should you wish to opt for this instead.
Long Loop Walk - Elevation: +400m/+1,312ft
Short Loop Walk - Elevation: +300m/+984ft

A beautiful renovated building with elegant decor. Villa Bela Vista is a boutique hotel located in the historic centre of Sintra, where rooms come with spectacular views of the National Palace and beyond.
Today you will explore Sintra-Cascais Natural Park. A short transfer (duration: 20min) will take you to the Convento dos Capuchos (Capuchos Convent), a classic example of an austere 16th-century Franciscan monastery, that you can visit before starting your walk. Continue through the picturesque Sintra hills to the shrine that is dedicated to the Virgin Mary of Peninha. The Santuário da Peninha is a remote and isolated chapel that stands up atop a craggy rock outcrop and has a dramatic location, which provides spectacular views over the entire Sintra coastline.
After passing Peninha, the trail continues through the lush vegetation of the park, with occasional glimpses of the coastline and the Atlantic Ocean in the distance. As you descend towards Azoia, you will notice some typical villages and lookout points along the way, where you can stop and take in the breathtaking scenery. Azoia itself is a charming village with a few restaurants and cafes and marks the end of this stage.
Elevation: +400m/+1,312ft

This gorgeous hotel features an outdoor swimming pool with an architecture rich in wood and stone details, it is located within a forest area, which includes a vineyard. Each of the 7 rooms is named after a different wine grape.
Enjoy a beverage while looking out at the sea or their garden. The property has panoramic views over areas like Guincho Beach, Cascais and the Atlantic Ocean.
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 Guincho Beach. From here you will receive a short transfer (duration: 15min) to your hotel in Cascais.
Elevation: +200m/+656ft
You may wish to opt for an extra night here, allowing you to have a free day to rest or explore the spectacular seaside town of Cascais and its trio of bays.

Check out after breakfast and make your way back to Lisbon by train for your onward travel connections (40 min).
This trip has a carbon score of 13kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 13kg is equivalent to 4 cheeseburgers. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?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.
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.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&Bs, inns, and guesthouses.
Solo Travellers, Families with Teens
The minimum age for this tour is: 12 Years
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.
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.
Meals
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.
Navigation
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!
- 4 nights in boutique hotels and charming guesthouses
- Breakfast at each accommodation
- Door-to-door baggage transfer as per itinerary
- Transfers as per itinerary
- 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
- Train travel between Lisbon and Sintra
- 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
Availability
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.
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.
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.
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).
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.
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.
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.
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.
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.
-
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.
-
Save %7 Days 6 Nights
Walking Sintra to Cascais
Walk through the Sintra-Cascais Natural Park, and discover palaces, castles and monasteries.Highlights- Walk through the Sintra-Cascais Natural Park
- The colourful UNESCO World Heritage Site of Sintra
- Stay in boutique hotels and charming guesthouses
-
Save %7 Days 6 Nights
Algarve Coastal Trails
Walk the Algarve Coast from Lagos to Cabo Sao Vicente, Portugal's most southwest point.Highlights- Walk quiet coastal trails through the Algarve
- Cabo Sao Vicente, Portugal's most southwest point
- Feast on fresh seafood and a glass of Alentejo red
-
Save %8 Days 7 Nights
Porto & the Douro Valley
Explore vibrant Porto and walk through the golden rolling hills of the Douro River Valley.Highlights- Discover Porto, a UNESCO World Heritage Site
- Enjoy tastings at local wineries
- A scenic river cruise down the Douro River
- 4 Days 3 Nights
Thames Path Short Break: Henley to Windsor
A short break walking from the regatta town of Henley-on-Thames to Windsor, home to the Royal PalaceHighlights- The world-renowned regatta town, Henley-on-Thames
- Marlow, where Mary Shelley penned Frankenstein
- The iconic royal palace of Windsor