Highlights
- Visit the chic coastal town of Cascais and the expansive Guincho Beach
- Stay in charming and historic hotels, including a restored 17th-century convent
- Explore Cabo da Roca, the westernmost point of Continental Europe
- Discover Sintra-Cascais Natural Park and UNESCO-listed Sintra Village
- Visit Monserrate Palace, the Moorish Castle, and Pena Palace
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Lisbon, Explore Cascais | Cascais |
| Day 2 | Transfer to Guincho Beach, Hike to Azóia | Azóia |
| Day 3 | Azóia Loop to Santuário da Peninha | Azóia |
| Day 4 | Hike to Colares via Cabo da Roca & Wild Beaches | Colares |
| Day 5 | Hike to Monserrate Palace & Sintra Village | Sintra |
| Day 6 | Sintra Loop via Moorish Castle & Pena Palace | Sintra |
| Day 7 | Transfer to Lisbon, Depart |
Detailed Itinerary
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, queens, writers, painters, and singers. The town was—and still is—home to many exiled foreigners, including World War II-era spies, Spanish kings, and British writers.
Depending on 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'll undoubtedly feel when you stroll in its streets and take in the gentle lullabies of the ocean. Wander the Museum Quarter to explore a handful of small museums, 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: Transfer to Guincho Beach, Hike to Azóia
Enjoy a hearty breakfast this morning before a short transfer to Guincho Beach, a stunning and windswept expanse of golden sand that's popular with local surfers. It's here that your hiking adventure begins. Start traversing the wide-open line of the coast, navigating 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.
It's a 6-mile (10 km) hike to get there, and once you arrive, you'll journey back in time as you enter the restored 17th-century convent. This tranquil accommodation will be your base for the next few days, so check in and relax, go for a dip in the pool, curl up by the fireplace with a drink or book, or organize a massage.
Day 3: Azóia Loop to Santuário da Peninha
This morning, take in the quiet melodies of nature as you fuel up with a delicious breakfast. After, prepare to hike the beautiful mountains of Sintra-Cascais Natural Park. Your trek today begins with a loop in the "moon hills," as Sintra Mountain was once known. Your 5.4-mile (9 km) trail ascends about 1,600 feet (488 m) above the sea to the Santuário da Peninha. When you reach the top, take a moment to rest and relish the breathtaking 360-degree panoramic view. Up here, you'll be surrounded by rugged paths within the forest and stunning vistas of the sea and landscapes beyond.
Take some time to explore nearby trails, enjoy a packed picnic lunch, 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.
Day 4: Hike to Colares via Cabo da Roca & Wild Beaches
After a delicious breakfast, you'll lace up your boots and hit the mountain trails again. This morning's 8-mile (13 km) trek will lead you to an unforgettable viewpoint over the cliffs where the ocean stretches as far as the eye can see. As your hike stretches on, you'll reach Cabo da Roca, the westernmost point of mainland Europe, where you can see the lighthouse that has been illuminating this coast since 1772. Detour and hike down to the ocean waters of Praia da Ursa, a wild and beautiful beach hidden along the rocky promontory here.
For lunch, visit the nearby beach of Adraga. Pause the restaurant for a grilled fish feast with ocean views, or grab a quick bite from the kiosk. Relax on the sand, splash in the waves then hit the trails toward the charming verdant 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 local wines.
Day 5: Hike to Monserrate Palace & Sintra Village
Fairy-tale romance awaits you on the trail today! Begin today's 7.75-mile (12 km) hike through the lush forest trails out of Colares, and enjoy verdant splendor en route to the impressive Monserrate Palace, a neo-Gothic mansion that serves as a brilliant example of Romantic architecture and design. Wander the grounds, admiring the unique detailed facade, 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 is a perfect introduction to the atmosphere that awaits you in the charming village of Sintra, a UNESCO World Heritage site that has inspired endless stories, myths, and legends. Stroll around the historic center, discover little intriguing details and romantic corners, and indulge in delicious regional pastry before returning to Colares.
Chat with a local specialist who can help organize your trip.
Day 6: Sintra Loop via Moorish Castle & Pena Palace
Today you'll explore the gorgeous hills above the village of Sintra. Here 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 a visit to the Castle of the Moors, a ninth-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.
From here, you'll also see the fabulous Pena Palace, one of the Seven Wonders of Portugal. This colorful national monument, an iconic expression of the Romantic period, is full of historical treasures and features exotic, lush gardens. After your hilly 4.5-mile (7 km) hike today, treat yourself to an exquisite dinner fit for royalty back in Sintra village.
Day 7: Transfer to Lisbon, Depart
A short transfer takes you back to Lisbon today, and depending on the time of your departing flight, you may be able to wander the streets of the capital and enjoy some last-minute souvenir shopping or eat a few pastéis de natas (Portuguese custard tarts). 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. Safe travels!
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