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Highlights
This walking tour in Sintra-Cascais Natural Park is the perfect playground for a beautiful hiking tour!
Hike to Guincho, a charming place known for its wineries and special vines planted in sandy soils and maritime climates.
Walk to the Cape Roca - the westernmost point of mainland Europe.
Visit the incredible Franciscan Capuchos Convent that stands out for its simplicity. Built-in the rock and lined up with cork.
Visit Monserrate Palace, a neo-gothic mansion revealing a brilliant example of the romantic period that left such an imprint in Sintra.
Looking for a shorter hiking tour that still has stunning landscapes? Then this 5-day, self-guided walking tour in the Sintra-Cascais Natural Park is the perfect playground for a beautiful hiking tour!
Located close to Lisbon, this walking tour starts in Cabo da Roca, the westernmost point of Continental Europe, and continues along its blue coastline.
As you head north, you will pass through wide bays of golden sand and breathtaking cliffs. Experience inland hiking, crossing the Sintra forest and its hilltops capped by luxuriant vegetation. You will also explore charming hotels, delicious gastronomy, and incredible UNESCO World Heritage sites.
Looking for a shorter hiking tour that still has stunning landscapes? Then this 5-day, self-guided walking tour in the Sintra-Cascais Natural Park is the perfect playground for a beautiful hiking tour!
Located close to Lisbon, this walking tour starts in Cabo da Roca, the westernmost point of Continental Europe, and continues along its blue coastline.
As you head north, you will pass through wide bays of golden sand and breathtaking cliffs. Experience inland hiking, crossing the Sintra forest and its hilltops capped by luxuriant vegetation. You will also explore charming hotels, delicious gastronomy, and incredible UNESCO World Heritage sites.
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Sintra 5-day Walking Itinerary
Day 1 Welcome to Portugal
After your arrival, a local representative will take you to Guincho, on the coastline close to the westernmost point of mainland Europe: Cape da Roca. Being part of the Sintra municipality, it is a charming place known for its wineries and special vines planted in sandy soils and maritime climates. It is recommended that you walk around and enjoy the ocean breeze, taste some good Portuguese food, and rest in your charming hotel in preparation for the days to come.
Overnight Location: Hotel in Guincho
Distance: None
Meals: None
Day 2 Explore and conquer the stunning Cape Roca
After a delicious breakfast, you will emerge into a scenery over the cliffs where the ocean stretches as far as your eyes can see. After you leave your accommodation, the path will lead you to Cape Roca – the westernmost point of mainland Europe, where you can see a beautiful lighthouse illuminating this coast since 1772. Along this rocky promontory hides a wild and beautiful beach, which goes by the name of Ursa (Bear)! You will also find the beautiful beach of Adraga, a great option for lunch. From here, you will head on to Praia Grande, where you will stay for tonight.
Overnight Location: Hotel at Praia Grande
Distance: 14km, 300m of ascent
Meals: Breakfast
Day 3 Discover the enchanted village and forests of Sintra
Today will be a gorgeous day! Leave Praia Grande and hike towards the forest. Surrounded by a unique beauty, you will find the incredible Franciscan Capuchos Convent, which stands out for its simplicity. Built-in the rock and lined up with cork, the convent is a witness of the humble and austere living of the Franciscan friars who lived there. Later, you will have the opportunity to visit the Monserrate Palace, a neo-gothic mansion revealing a brilliant example of the romantic period that left such an imprint in Sintra. Your day will end at the historical center of Sintra’s village. Use your free time to stroll around the village and discover intriguing details, romantic corners, and delicious regional pastries.
Overnight Location: Hotel at Sintra
Distance: 14-20km, 500-700m of ascent
Meals: Breakfast
Day 4 Explore the hills above the village of Sintra
Enjoy the vast architectural patrimony set on the mountain. Such is the grandeur and importance of these buildings and monuments that Sintra’s cultural landscape was designated as a UNESCO World Heritage site in 1995. Visit the Moorish Castle and the fabulous Pena Palace, with its exuberant and exotic gardens. Today, you will feel like a king or queen, finishing the evening with an exquisite dinner at the village center.
Overnight Location: Hotel at Sintra
Distance: 10km, 400m of ascent
Meals: Breakfast
Day 5 Transfer to Lisbon
That’s it! Tour program comes to an end. We hope the memories and experiences you have created and shared stay with you forever.
Overnight Location: None
Distance: None
Meals: Breakfast
2026 Pricing for Sintra 5-day Walking Tour The departures are available starting daily from January 4 to December 15, 2026.
The starting price for two people sharing a double or twin room is EUR575 per person.
Accommodation on Sintra 5-day Walking
This tour is mostly based in charming and superior accommodation. All rooms will have private washrooms.
In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.
Single Rooms and Solo Travellers
Rooms are double occupancy. You can pay a supplement to have a private room in a hotel where possible. Solo travellers may be required to pay a supplement.
What’s Included in the Sintra 5-day Walking?
Meals
4 breakfasts are included.
Accommodations
Accommodations for 4 nights are included. Accommodations before the tour are not included but can be added as a supplement.
Transportation during the Tour
This tour includes airport pickup and drop-off, luggage transfers from hotel to hotel and short transfers mentioned in the itinerary.
Also included
- Welcome briefing in English
- Digital Information Book delivered before the tour
- Smartphone App & GPS tracks
- Local Support Number (Free to call 24h/day)
- Pre-departure Information Pack (checklist, general travel information)
- Tour Information (description of daily stages & profiles)
Not included
- Any personal transport
- Flights
- Meals, drinks, or snacks not previously mentioned
- Tips
- Gratuities for tour guides or other staff if desired
Optional Extras
- Additional nights before or after the tour
- GPS Device (Garmin Oregon)
- Different arrival & departure transfers
- Tickets for Pena Palace, Monserrate Palace, Moorish Castle and Capuchos Convent
- How hard is the Sintra 5-day Walking?
- Do I need a visa to travel to Portugal?
- Are meals included on the Sintra 5-day Walking?
- Do I need insurance?
- How do I get to Praia Grande to start this tour?
- Where does the Sintra 5-day Walking end?
- Do I need special vaccines to travel to Portugal?
- Are there any travel restrictions for Portugal?
We rate the difficulty of this tour as a 3 / 5. Although the terrain is not challenging, you will be walking up to 20 km daily. If you do this in July and August the heat can make this a very challenging walk.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
4 breakfasts included.
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover walking. Get your travel insurance.
Fly into Lisbon. From there you will be picked up and driven to your first hotel.
The tour ends in Sintra and you will be transferred to Lisbon Airport.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
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