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

Day 1- Arrival at Cascais

Welcome to Portugal!

Our guide will pick you up and transfer you to your first hotel accommodation, where you’ll be introduced to the journey ahead. During a brief briefing, our guide will provide an overview of the exciting days to come, detailing the tour itinerary and key highlights. Besides that, the day it’s yours to explore Cascais! With over 650 years of history, this charming town has long attracted kings, queens, writers, painters, and musicians, making it a true symbol of elegance and inspiration. Take some time to stroll through its historic streets, discover its architectural treasures, relax on its stunning beaches, and savor the delicious local cuisine. Your adventure begins here – let the charm of Cascais captivate you!

Discover the beautiful coastline of Cascais.

Today’s hike invites you to experience the breathtaking landscapes along Cascais’ rugged coast. You can choose between starting your hike from your hotel, passing through the Boca do Inferno (Hell’s Mouth), or after a short car transfer that will take you to the Crismina Dunes, which sits just next to Guincho Beach. From here, the trail follows a secluded valley with sweeping ocean views, offering a challenging route that ascends toward Azóia.  Along the way, you’ll be immersed in the area’s natural beauty and rich history, discovering historic sites like Guincho Fort, once a vital stronghold against invaders. Once you arrive, take a moment to relax and fully immerse yourself in the breathtaking ocean vistas, or treat yourself to an unforgettable meal showcasing the rich and authentic flavors of the region. Optional transfer from Cascais to Guincho (shorter option) (10 min)

Prepare to be captivated by the breathtaking beauty of the Sintra mountains! Today, you’ll embark on a circular hike through the enchanting ‘Moon Hills’—the charming hills of Sintra. The highlight of your adventure will be reaching one of the highest points, Peninha, home to the stunning sanctuary of Peninha. Take a moment to relax and soak in the panoramic views of the coast, a truly unforgettable sight. After exploring the sanctuary’s surroundings, a gradual descent will lead you through a cool, lush forest, where the vistas continue to impress. This is the trail where many of the Sintra photos are taken with the special light, with sun rays filtering through the tall trees and the misty, magic-like mornings.  As you walk along the elegant paths, you’ll be surrounded by the serene beauty of both land and sea, providing the perfect opportunity to embrace the tranquility and contemplate the vastness of the sky. 

After a delightful breakfast, prepare to step into a world of dramatic cliffside views, where the ocean stretches endlessly before you. Here lies Cape Roca, the westernmost point of mainland Europe – a place once thought to be the very edge of the world. Surrounded by immense natural beauty, this iconic spot features spectacular cliffs and unique coastal trails. Hide along this rocky promontory is the wild and beautiful Ursa (Bear) beach, along with the remarkable Fojo, a deep natural well that connects to the sea below. Formed by the erosion of limestone rocks, the cave echoes with the sound of waves crashing against the rocks at its base, creating a fascinating natural spectacle. As you continue toward Praia Grande, where you’ll spend the night, you’ll pass the picturesque Adraga Beach, home to the iconic Pedra de Alvidrar, or “Rock of Reason” – a sight not to be missed. End your day admiring a stunning sunset over the Atlantic, the perfect finale to an unforgettable journey along the coast.

Discover Sintra, Portugal’s Fairytale Town!

The day starts from the beach and then heads into the enchanting Sintra Forest, where you’ll have the opportunity to visit some of the area’s most iconic and unmissable places, like the Capuchos Convent and Monserrate Palace. Known as the Cork Convent, this Franciscan convent stands out for its sheer simplicity. Founded in 1560, in a remote part of the Sintra, this monastic retreat was established in a place shrouded in lush greenery, for  Franciscan friars who sought a life of extreme austerity, simplicity, and solitude. Later on this day, you’ll reach the Monserrate Palace, a Neo-Gothic masterpiece surrounded by lush, landscaped gardens. Take time to wander through its beautiful rooms adorned with Gothic, Indian, and Moorish influences and discover exotic plant motifs that blend harmoniously with the botanical gardens, creating one of Portugal’s most remarkable outdoor spaces. After your visit, you can choose to continue hiking to Sintra or opt for a quick ride by taxi or bus. For those who prefer to complete the hike, a scenic descent brings you to Sintra, where you’ll stay for your last two nights. This experience is the perfect introduction to the atmosphere of Sintra’s village, where you can explore the historic center and uncover little intriguing details, romantic corners, and some delicious regional pastries.  The short option requires taking the City Bus from Monserrate to Sintra (not included). 

Explore the Majestic Hills of Sintra.

Today is all about discovering the treasures nestled in the hills above the village of Sintra. This region, a UNESCO World Heritage site since 1995, offers a captivating blend of architectural splendor and natural beauty. As you wander through Sintra’s enchanting mountain trails, you’ll pass magnificent castles, palaces, and historic manors that tell stories of Portugal’s regal past. Although there are multiple sites of interest, the day is reserved for two of the most emblematic monuments of Sintra, the fabulous Pena Palace, renowned for its vibrant colors and lush, exotic gardens, and the ancient Moorish Castle, a 10th-century fortress with breathtaking views over Sintra and the surrounding coast. End your day in Sintra’s village, where the magic continues. Stroll through charming streets, soak up the romantic ambiance, and treat yourself to a royal dining experience – a perfect finish to an unforgettable day in one of Portugal’s most enchanting locations.