Portugal Self-Guided Walking Tour – Sintra Heritage & Coastal Trails

Tour Dates: Year around with the best weather in May – October

The greatest shapes of Sintra!  At a close distance from Lisbon, lies the Sintra – Cascais Natural Park, which is the perfect playground for this beautiful hiking tour! This route starts in the lovely town of Cascais and takes you along its blue coast, through wide bays of golden sand and some breathtaking cliffs. The most stunning of them all is Cape Roca – the westernmost point of Continental Europe!  Experience the great hiking inland, when you cross the Sintra Forest and its hilltops that are capped by luxuriant vegetation. During this time, you will also explore charming hotels, delicious gastronomy, and incredible UNESCO World Heritage site.


2023 Price: €1200 Euros

Single Supplement: €600 Euros High Season (May 28 – October 28): €1,450 Single Supplement: €800 Euros
Price Includes:
  • Transfers from Lisbon at the beginning and end of the tour
  • 6 nights lodging with breakfast
  • Welcome briefing
  • Digital information book made available before tour start.  (Daily Information, Daily Maps, Restaurant recommendations, etc.
  • Navigation app to download to your phone
  • Luggage transfers
  • Mobil telephone number local cell phone support
Price Does Not Include:

International flights, lunches and dinners, tips, Drinks, City taxes

Tour Difficulty


  • Distances average 6 – 20 km/day.  The terrain is hilly on coastal trails, dirt roads and forest trails.

Tour Highlights

  • Cascais-Sintra Natural Park and  UNESCO World Heritage sites
  • Beautiful town of Cascais
  • Traditional gastronomy and fresh fish from the Atlantic Coast


Day 1- Arrival in Lisbon

Welcome to Portugal! One of our guides will transfer you to Cascais, which should take about 30 minutes. You might get the chance to explore this delightful town, a village with 650 years of history that was forged by fishermen, but later populated by kings, queen, writers, painters and singers.

However, this all depends on your arrival time! Deep down, Cascais is a synonym for charm and inspiration, something you will undoubtedly feel if you have the chance to walk in its streets and listen to gentle lullabies of the ocean. This is the perfect beginning for this trip, which can be celebrated with a delicious fresh fish dinner at the village center!

Day 2 – Hike from  Cascais to Azoia  Hike: 10 or18  km, Elevation gain: 300 or 400 meters

This day will start with a short transfer to Guincho where your hike starts. Experience a wide open line of coast between dunes, valleys and small villages. You will feel a rural atmosphere with a touch of luxury, as the presentation of the past uniting with the present. The objective for today is to reach the Convent of São Saturnino at the head of a secluded valley. Go back in time and experience this 17th century recovered convent, which will be your accommodation for the next couple of days. It is a peaceful location where the sea and the mountains meet.

Day 3 – Hike Azoia Loop   Hike: 10 km, Elevation gain: 300 meters

The mountain of Sintra will immediately take your breath away! You will be starting with a circular walk into the “moon hills” as Sintra Mountain was known! This route goes up to 488 meters above the sea, where you will find the sanctuary of Peninha. This will be a moment to just lay back and enjoy the breathtaking panoramic view. Up here, you will be surrounded by elegant paths within the forest and accompanied by the beauty of both the sea and land. This is the perfect place to enjoy the silence and contemplate the endless sky.

Day 4 – Hike from Azoia to Praia Grande   Hike: 14 km, Elevation gain: 300 meters

After a delicious breakfast, you will emerge into a scenery over the cliffs where the ocean stretches as far as your eyes can see. Then comes Cape Roca-the westernmost point of mainland Europe, where you can see a beautiful lighthouse which has been illuminating this coast since 1772. Along this rocky promontory, hides a wild and beautiful beach which goes by the name of Ursa! 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.

Day 5 – Hike Praia Grande to Sintra   Hike: 14 or 20 km, Elevation gain: 500 or 700 meters

Today will be a gorgeous day! Start from the beach area and hike on the forest trails leading you to Capuchos Convent and then Monserrate Palace, a neo-gothic mansion revealing a brilliant example of the romantic period that left such an imprint in Sintra. There is a short track option for this day. This experience will be a perfect introduction to the atmosphere of Sintra’s village, where you can stroll around the historic center and discover little intriguing details, romantic corners and some delicious regional pastry.

Day 6 – Hike Sintra Loop   Hike: 6 or 10 km, Elevation gain: 300 or 400 meters

This day will be reserved for exploring the hills above the village of Sintra. The aim is to enjoy the vast architectural patrimony that is set on the mountain. Such is the grandeur and importance of these buildings and monuments. The cultural landscape of Sintra was designated as an UNESCO World Heritage site in 1995 with the Moorish Castle and also the fabulous Pena Palace, with its exuberant and exotic gardens. Today, you will feel like a king or queen and finish the evening with an exquisite dinner at the village center.

Day 7 – Departure Transfer to Lisbon

That’s it! Our splendid program comes to an end. We hope that the memories and experiences that we have created and shared stay with you forever.