Expedition Overview

Expedition Overview

  • Explore the Douro wine region and the royal resort town of Sintra—both UNESCO World Heritage sites—and experience a performance of fado, part of UNESCO’s Intangible Cultural Heritage of Humanity.
  • Hike along coastal beaches and dramatic cliffs to Cabo da Roca, the westernmost point of continental Europe, and kayak the idyllic Douro River.
  • Trek through the stunning Serra da Estrela Natural Park—home to mainland Portugal’s loftiest peak—and discover quaint stone villages seemingly untouched by time.
  • Tour the Douro Valley’s world-class vineyards and learn about traditional bread making in picturesque Favaios.

Itinerary

Itinerary

At mainland Europe’s western edge lies one of its lesser-known gems—a land of wild coasts, terraced vineyards, and historic cities whose cobbled streets tell a multitude of stories. Experience the beauty of Portugal as you trace the beaches and cliffs that hug the Atlantic shore, and trek through the verdant forests of Serra da Estrela Natural Park. Hike and kayak in the acclaimed Douro Valley wine region; explore charming villages; and round off your journey with a stirring performance of fado, the soul of Portuguese music.

Day 1: Lisbon, Portugal

Arrive in Lisbon and settle into our elegant hotel, located in the heart of the city. Explore the captivating Portuguese capital on foot, climbing the cobblestoned streets of the historic Alfama district, strolling through multicultural Mouraria, and taking in panoramic views from the ramparts of São Jorge Castle. Gather for a welcome dinner this evening. (2 hours walking)

Meals Included:Dinner
Accommodations:Hotel Pousada de Lisboa
Day 2: Cabo da Roca/Sintra

Follow the Atlantic coast from Lisbon to the picturesque village of Almoçageme. This is our starting point for a coastal hike to Cabo da Roca—the westernmost point of continental Europe. From Almoçageme, cross a small forest to reach the cliffs overlooking the Praia Grande (or big beach) and Praia da Adraga (Adraga Beach). Climb up to the top of the cliffs, passing secluded coves and valleys en route to the Cabo da Roca lighthouse. At the end of the hike, transfer to the enchanting town of Sintra, nestled amid lush hills at the edge of a nature reserve. Check in to our 18th-century hotel, and head out for an optional guided stroll through Sintra’s historic center. (5 miles hiking, 5–6 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Tivoli Palácio de Seteais Hotel
Day 3: Sintra-Cascais Natural Park

After breakfast, head to Santuario da Peninha, a remote chapel perched atop a rocky, windswept crag in Sintra-Cascais Natural Park. Enjoy breathtaking views of the rugged Atlantic coastline as you embark on one of the area’s most spectacular hikes, winding down through cedar forests to the golden beach of Guincho. Return to Sintra and enjoy time at leisure in this beautiful town, which was once a favorite haunt of English Romantic poet Lord Byron and Portuguese royalty. (5–6 miles hiking, 4–5 hours)

Meals Included:Breakfast, Lunch
Accommodations:Tivoli Palácio de Seteais Hotel
Day 4: Serra da Lousã/Serra da Estrela Natural Park

This morning, depart for Serra da Estrela Natural Park—home to the highest mountain range in Portugal. Along the way, stop at the town of Lousã and have lunch in front of the 11th-century Arouce Castle (also known as Lousã Castle), surrounded by forests of oak, chestnut, and pine. From here, we hike on wooded paths to two quaint schist villages—clusters of centuries-old cottages made of local schist stone, which have recently been restored. Later, drive to our hotel, located within the verdant folds of Serra da Estrela Nature Park. (4 miles hiking, 3–4 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Casa das Penhas Douradas Design Hotel & Spa
Day 5: Serra da Estrela Natural Park

Wake up amid the breathtaking beauty of the Serra da Estrela, where mirror-like lakes reflect the dramatic granite peaks above, and forests ring with the song of over 150 species of birds. Set out to explore the 5,000-foot high Penhas Douradas plateau, trekking across woodlands and rocky valleys dotted with shepherds’ huts. Pause at the Vale do Rossim lake for lunch, and continue to the hillside village of Manteigas. Here, we take a tour of the restored Burel Factory, where burel—a traditional woolen fabric—has been manufactured since the 18th century. Enjoy free time before gathering for dinner at our hotel. (5–6 miles hiking, 4–5 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Casa das Penhas Douradas Design Hotel & Spa
Day 6: Douro Valley

This morning, follow the Douro River into the terraced vineyards of the stunning Douro Valley, where some of Portugal’s best wines and ports are produced. Begin your hike in the charming village of Provesende—which boasts elegant old buildings with wrought iron balconies—and meander along rolling vineyards to the sleepy riverside town of Pinhão. From here, we drive to our hotel, located on a family-owned wine estate. Return to Provesende tonight for dinner at a local restaurant. (4 miles hiking, 3–4 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Casa das Pipas at the Quinta do Portal Vineyard
Day 7: Pinhão/Douro River

Today, head to Pinhão and board a rabelo, a traditional wooden cargo boat native to the region. Glide up the Douro to its junction with the Tua River, and kayak back down to Pinhão, paddling past scenic port wine estates. Pause for a picnic lunch and an optional swim at a sandy beach, accessible only by boat. Enjoy a final walk through the region’s vineyards, and cap off the afternoon with a wine tasting at our hotel’s award-winning cellar. (7–8 miles kayaking, 4 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Casa das Pipas at the Quinta do Portal Vineyard
Day 8: Favaios/Porto

After breakfast, transfer to the scenic village of Favaios, known for its production of moscatel wine and “four-cornered” bread. Visit a traditional bakery to observe local bakers prepare their signature buns in a wood-fired oven; then set out on a hike across the Favaios plateau, crisscrossing tranquil vineyards on well-worn trails. Our hike culminates at a family-run wine estate, where we enjoy a wine tasting and lunch. Drive to Porto, and relax at our hotel before heading to a local wine cellar for a performance of fado, an evocative form of Portuguese folk singing. Celebrate your adventure with a farewell dinner at the wine cellar. (4 miles hiking, 3–4 hours)

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Pestana Vintage Porto
Day 9: Porto

After breakfast, transfer to the airport for your flight home.

Meals Included:Breakfast