Discover Portugal's wild side on this eight-day coastal hiking trip. The adventure will begin with a food tour of Lisbon and a rest day in the gorgeous beach town of Cascais. Spend the next four days trekking around the expansive Sintra-Cascais Natural Park, passing through forests, dunes, coastal towns, and hilltop sanctuaries. End with some downtime in Sintra, a charming village known for its impressive palaces and castles.


  • Have a beach day in the glamorous seaside town of Cascais
  • Trek through the Sintra Mountains to the hilltop Peninha Sanctuary 
  • Hike to Cabo da Roca, the westernmost point in mainland Europe
  • Visit three of Sintra's famous 19th-century palaces

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon & Gourmet Food Tour Lisbon
Day 2 Transfer from Lisbon to Cascais  Cascais
Day 3 Hike from Cascais to Azóia Azóia
Day 4 Complete the Azóia Loop Azóia
Day 5 Hike from Azóia to Colares Colares
Day 6 Colares to Sintra Hike & Palace Visit Sintra
Day 7 Tour of Sintra Palaces & Sintra-Cascais Natural Park Sintra
Day 8 Transfer from Sintra to Lisbon & Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon & Gourmet Food Tour

Praca do Comercio, Lisbon's main square
Praça do Comércio, Lisbon

Welcome to Portugal! Medieval castles, cobblestone villages, captivating cities, and golden beaches await. But first, a driver will greet you at the Lisbon airport and transfer you to your hotel. Spend your free afternoon resting or visiting sights like Castelo de S. Jorge (St. George Castle) and Praça do Comércio, the city's main square.

When evening hits, take part in a gourmet food tour of Lisbon—a great way to experience the city for the first time! Meander through a series of winding alleys, tasting the incredible flavors of Portuguese gastronomy in the neighborhood of Campo de Ourique.

Day 2: Transfer from Lisbon to Cascais

Cascais lighthouse
Cascais, a famous beach town

Early in the morning, a driver will pick you up from your hotel and transfer you to Cascais. Once a sleepy fishing village, this town is now an upscale beach resort. As it's only about a thirty-minute drive from Lisbon, people from the capital often come here to enjoy the refreshingly cold water of the Atlantic Ocean.

Flush with gorgeous urban beaches and dramatic rock formations, Cascais entices you to take long strolls along the coast. Pull yourself away from the sea long enough to visit the charming old town, where colorful flowers hang from balconies over pastel houses. For dinner, try delicious local specialties like octopus or fresh seafood.

Day 3: Hike from Cascais to Azóia

The stunning scenery of the Estoril Coast
The stunning scenery of the Estoril Coast

Enjoy a hearty breakfast before transferring to Guincho Beach, where your hiking adventure begins. You'll be traversing the scenic Estoril Coast. As you hit the trail, experience a wide-open shoreline between dunes, valleys, and small villages.

Your destination is the beautiful Convent of São Saturnino, situated at the head of a secluded valley in Azóia where the sea meets the mountains. Go back in time and experience this restored 17th-century convent, where you have the chance to stop and recover your strength. Drinks, massages, and a pool are available for those needing a break.

Hiking distance: ~ 6 miles (10 km) 

Day 4: Complete the Azóia Loop

Peninha Santuary, Sintra
Peninha Sanctuary in the Sintra Mountains
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This morning, take in the quiet melodies of nature as you fuel up for the day with a delicious breakfast. Then, prepare to complete the scenic loop trail in the Sintra Mountains. The range was once called the "Moon Hills" because legend claimed that Diana, the Roman goddess of the moon, came here to rest and hunt.

Your trail ascends about 1,600 feet (488 m) to the Peninha Sanctuary. When you reach the top, take a moment to rest and admire the breathtaking panoramic view. Up here, you will be surrounded by elegant paths within the forest and stunning vistas of the sea. Once you've recovered your breath, continue back to the beginning of the trail.

Hiking distance: ~ 5.5 miles (9 km)

Day 5: Hike from Azóia to Colares

Cabo da Roca
Cabo da Roca coastline

Today's hike will begin early. Walk up coastal cliffs until you emerge onto an unforgettable viewpoint where the ocean stretches as far as the eye can see. Continue to Cabo da Roca, the westernmost point of mainland Europe. Here, you can see the iconic lighthouse that has been illuminating this coast since 1772. Cool off in the wild and beautiful Ursa Beach.

Once hunger hits, make your way to nearby Adraga Beach, a perfect lunch spot. Have a bite, relax on the sand, and splash in the waves. Then, head on to the pretty village of Colares, where you will stay for the night. At dinner, consider indulging in delicious, freshly caught seafood paired with a glass of local wine.

Hiking distance: ~ 8 miles (13 km)

Day 6: Colares to Sintra Hike & Palace Visit

Monserrate Palace in Sintra
Monserrate Palace in Sintra

Fairy-tale romance awaits you on the trail today. Start your hike on forest trails outside of Colares. Take in the verdant splendor of the area's woods as you make your way to the town of Sintra, known for its numerous castles and palaces.

The hike will end in Sintra's impressive Monserrate Palace, a neo-Gothic mansion that is a brilliant example of Romantic architecture. Wander the grounds, admire the unique detailed façade, then indulge in the visual feast of its interior. Beams of sunlight illuminate elaborate sculptures, beautifully preserved busts, and intricate cupolas. Afterward, stroll around the historic center of Sintra.

Hiking distance: ~ 7.75 miles (12 km)

Day 7: Tour of Sintra Palaces & Sintra-Cascais Natural Park

Quinta da Regaleira, Sintra
Quinta da Regaleira, Sintra

Spend the morning touring two of Sintra's famed palaces. Walk around Pena Palace, known for its unusually colorful facade. Perched on top of a hill, it is the town's most iconic landmark. Next, visit Quinta da Regaleira, an opulent 19th-century estate. The neo-Gothic palace certainly draws attention, but it's the gardens that fascinate people with their elaborate spiral wells and secret cave passages.

Both of these palaces are part of the expansive Sintra-Cascais Natural Park. Your guide will take you to other points of interest within the area, like the large Cresmina Dune and the Stone Age dolmen of Anta de Adrenunes, or you can head back to spend some more time at the popular spots of Cabo de Roca and Guincho Beach. 

Day 8: Transfer from Sintra to Lisbon & Depart

Scenic terrace in Lisbon
A scenic terrace in Lisbon
Enjoy a final morning amid the beauty of Sintra. At the designated time, a private driver transfer will take you to Lisbon Airport to catch your flight back home. Safe travels and boa viagem!

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Map of Portugal Scenic Coastal Hike: Cascais, Azóia, Colares & Sintra - 8 Days
Map of Portugal Scenic Coastal Hike: Cascais, Azóia, Colares & Sintra - 8 Days