Perfect for nature lovers, this 8-day tour winds its way from the pretty beach town of Cascais, through the westernmost point on the European continent, and across the Sintra-Cascais Natural Park. Experience verdant Portuguese forests, overnight in charming hotels, revel in the delicious local gastronomy, and check some stunning UNESCO World Heritage Sites off your must-see list.


  • Visit mainland Europe's westernmost point
  • Hike through peaceful Portuguese forest
  • Visit charming Sintra
  • Spend two nights in the 12th-century Convent of São Saturnino

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Portugal Cascais
Day 2 Cascais to Azóia Azóia
Day 3 Azóia loop Azóia
Day 4 Azóia to Colares Colares
Day 5 Colares loop Colares
Day 6 Colares to Sintra Sintra
Day 7 Sintra loop Sintra
Day 8 Departure  

Detailed Itinerary

Day 1: Arrive in Portugal

The charming streets of Cascais

Welcome to Portugal! Make your way to Cascais and settle in. If you arrive early enough, spend some time exploring this 650-year-old fishing village, beloved by kings, queens, writers, painters, and singers. When locals think of Cascais, they think of charm and inspiration (and it's easy to see why). Wander the pedestrian streets. Relax beside the quiet waves of the bay. And enjoy a delicious, fresh fish dinner in the village center before turning in for the night.

Day 2: Cascais to Azóia


Put on your hiking boots, grab your camera, and transfer to Guincho where you'll start your first hike. The landscape here is one of wide open coastline, dunes, valleys, and tiny rural villages with modern luxurious touches. Wind your way along the coast to the 12th-century Convent of São Saturnino in Azóia on the edge of a secluded valley. This is where you'll stay for the next couple nights. 

Hiking distance: 6 miles

Day 3: Azóia Loop

You'll stay in the relaxing and beautiful Convent of São Saturnino
You'll stay in the relaxing and beautiful Convent of São Saturnino

On your second day of hiking, make your way up the so-called Moon Hill (Sintra Mountain) where you'll find the Santuário da Peninha — a shrine perched on a rocky outcropping. Pause here to soak in the breathtaking 360-degree views of sea, land, and sky. Then make your way back down to the convent for the night.

Hiking distance: 5.5 miles

Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Day 4: Azóia to Colares

Cape Roca
Cape Roca

Enjoy a delicious breakfast and then make your way to Cape Roca — mainland Europe's westernmost point — where a charming lighthouse built in 1772 stands watch. Continue along the rocky promontory to wild, beautiful, hidden Ursa Beach and then onto the sunny, rock formation-dotted Adraga Beach — a perfect place to stop for lunch. After lunch, take to the trails again, making your way to the village of Colares and your next hotel. 

Hiking distance: 8 miles

Day 5: Colares Loop

The seaside town of Azenhas do Mar near Colares

On your fifth day in Portugal, follow a leisurely, circular route into the heart of Sintra's forests. Here, you'll find the Capuchos Convent — built according to a philosophy of harmony and respect between humans and the divine. From there, meander back to charming Colares for lunch and a glass of wine at the Colares Winery.

Hiking distance: 7.5 miles

Day 6: Colares to Sintra

Sintra, Portugal
Sintra, Portugal

Put on your boots for another day of hiking — this time along pretty forest trails to the impressive neo-gothic mansion, Monserrate Palace. Explore the eclectic palace and its grounds and then make your way to Sintra for a stroll through the historic center and a taste of some exceptional regional pastries before retiring to your boutique hotel.

Hiking distance: 7.5 miles

Day 7: Sintra Loop

Pena Palace

Make your way into the UNESCO-recognized hills above Sintra to explore the Castle of the Moors and the grand Pena Palace with its exuberant, exotic gardens. When you've had your fill of castle walls and sweeping grounds, wander back down the hills to Sintra for a final exquisite dinner in the village center. 

Hiking distance: 4.5 miles

Day 8: Departure


Bid the lovely, verdant hills and the charming villages farewell! It's time to make your way to the airport and home, or extend your trip and explore more of the incredible Portuguese landscape. Other popular destinations in the country include pretty Lisbon, vibrant Porto, and the beachy Algarve Coast.


Map of Sintra Heritage & Coastal Trails - 8 Days
Map of Sintra Heritage & Coastal Trails - 8 Days