Portugal: Sintra Heritage & Coastal Trails Hike - 7 Days

Day 1: Arrive in Lisbon & explore Cascais

Welcome to Portugal! After you land in Lisbon, you'll have a 30-minute transfer to the delightful town of Cascais, a 650-year-old village forged by fishermen but later populated by kings, queen, writers, painters and singers. The town was — and still is — home to many exiled foreigners, including WWII-era spies, Spanish kings, and British writers. 

Depending one the time of your arrival, you may be able to stretch your legs and explore the town; deep down, Cascais is synonymous with charm and inspiration, something you will undoubtedly feel when you stroll in its streets and take in the gentle lullabies of the ocean. There all some nice (albeit small) museums here, including one dedicated to Paula Rego, a contemporary Portuguese painter. Celebrate the beginning of your trip tonight with a delicious fresh fish dinner at a quaint eatery in the village center!

Day 2: Cascais to Azóia

Enjoy a hearty breakfast this morning before a short transfer to Guincho, where your hiking adventure begins.

When you hit the trail, you'll experience a wide open line of coast between dunes, valleys and small villages. Your destination today is the gorgeous Convent of São Saturnino at the head of a secluded valley in Azóia, where the sea and mountain meet. Go back in time and experience this restored 17th century convent, which will actually serve as your tranquil accommodation for the next days.

After you check-in, go for  a dip in the pool, lounge with a great book and a drink by the fireplace in the main hall, or take advantage of the on-call massage service.

Distance: About 6 miles (10 km) 

Day 3: Azóia Loop

This morning, take in the quiet melodies of nature as you fuel up for the day with a delicious breakfast. Then prepare for the beautiful mountain of Sintra to take your breath away on the trail!

Your trek today begins with a loop in the "moon hills," as Sintra Mountain was once known. Your trail ascends about 1,600 feet ( 488 m) above the sea to  the sanctuary of Peninha. When you reach the top, take a moment to rest and relish the breathtaking panoramic view; this viewpoint is the perfect place to quietly contemplate the endless sky. Up here, you will be surrounded by elegant paths within the forest and stunning vistas of the sea and landscapes beyond.  

Take some time to explore nearby trails or head back to your hotel to relax for the rest of the day. At sunset, head outside to watch the sun dip behind the horizon and enjoy a great night's sleep ahead of tomorrow's adventures. 

Distance: About 5.5 miles (9 km) 

Day 4: Azóia to Colares

After a delicious breakfast, it's time to hit the trail again: this morning you'll emerge onto an unforgettable viewpoint over the cliffs where the ocean stretches as far as the eye can see.

As your hike stretches on, you'll come to Cabo da Roca, the westernmost point of mainland Europe, where you can see the beautiful light house that has been illuminating this coast since 1772. Cool off in the ocean waters of Ursa, a wild and beautiful beach hidden along the rocky promontory here. You can also head to the nearby beach of Adraga, the perfect spot for lunch.

Have a bite, relax on the sand, splash in the waves, then head on to the charming village of Colares, where you will stay for the next two nights. At dinner tonight, consider indulging in delicious, freshly caught seafood paired with the area's wonderful local wines!

Distance: About 8 miles (13 km)

Day 5: Colares to Sintra

Fairytale romance awaits you on the trail today! Start your hike on forest trails out of Colares and enjoy verdant splendor en route to the impressive Monserrate Palace, a neo-gothic mansion that serves as a a brilliant example of Romantic architecture and design.  Wander the grounds, admiring the unique detailed façade, then indulge in the fantasy of the incredible interior, where beams of sunlight illuminate elaborate sculptures, beautifully preserved busts, and vibrant cupolas. 

Exploring Monserrate Palace isbe a perfect introduction to the atmosphere that awaits you in the charming village of Sintra, where you can stroll around the historic center, discover little intriguing details and romantic corners, and indulge in delicious regional pastry.

Distance: About 7.75 miles (12 km)

Day 6: Sintra Loop

Today you'll explore the gorgeous hills above the village of Sintra; you'll enjoy not only the lush landscape but a collection of architectural gems whose grandeur and importance merited Sintra a designation as a UNESCO World Heritage site.

Tap into your inner royal with visits to Starting with the Castle of the Moors, a 9th century citadel  that served as an important strategic point during the Reconquista. From the hilltop you'll be treated to a panoramic vista of Sintra below, and the ivy-flanked remnants of the fortress lend an aura of romance to the site. You'll also see the fabulous Pena Palace, one of the Seven Wonders of Portugal. This national monument, an iconic expression of the Romantic period, is full of historical treasures (check out the Chapel and the luxurious Royal Dining Room) and features exotic, lush gardens.

Treat yourself like a queen or king tonight back in Sintra as you end your day with an exquisite dinner in town. 

Distance: About 4.5 miles (7 km)

Day 7: Departure from Lisbon

Depending on the time of your departure flight today, you may be able to hit the streets of Lisbon for some last-minute shopping or a final egg tart (or two!). Or head out to one of the city's miradouros — viewpoints with gardens — for one last look at Portugal's romance. When the time comes, you'll be transferred to the airport for your flight home or onto your next adventure. 

See Europe's best itineraries, which includes this trip.