Highlights
- 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
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
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
Chat with a local specialist who can help organize your trip.
Day 4: Azóia to Colares
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
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
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
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.
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