At mainland Europe’s western edge lies one of its lesser-known gems—a land of wild coasts and broad beaches, lush forests and terraced vineyards, and cities whose cobbled streets tell long histories. Experience the charms of Portugal as you hike and kayak in the wine country of the Douro Valley and sample fine ports in enchanting Porto. Explore Moorish castles in Lisbon and Sintra, and trace the beaches and cliffs that line the Atlantic to the continent’s westernmost point.
Arrive in Porto and settle in to our hotel. After lunch, head out on foot to explore the narrow streets of the historic old town. Take in views across the Douro River from Praça da Ribeira, and walk along the riverfront, spanned by iron bridges. Gather for a welcome dinner tonight.
Travel by bus to Peso da Régua following the rural landscape of the north of Portugal and the Douro River into the terraced vineyards of the stunning Douro Valley, where some of Portugal’s best wines and ports are produced. In Régua we will visit the Douro Museum for our first introduction to the region and the stories behind its wine-making tradition. After lunch, drive through rolling landscapes to our trail, which climbs from the river’s edge into the hills, offering spectacular views of vineyard-striped slopes and the meandering river below. (5 miles hiking, 4 hours)
Board a rabelo, a traditional wooden cargo boat native to the region, and glide up the Douro to its junction with the Tua River. Kayak back down to Pinhão, paddling past charming port wine estates and pausing for a swim or a snack at sandy beaches best accessible by boat. Enjoy a final walk through the region’s vineyards, capped off by a wine tasting. (7–8 miles paddling, 4 hours; 1-2 miles hiking, 1 hour)
Return to Porto, stopping en route for a visit to the house and gardens of Casa de Mateus, an ornate manor house that exemplifies Portuguese baroque architecture. Arrive back in Porto, and later this afternoon, cross the river to visit a port wine cellar where we’ll sample the city’s most famous export.
The next day, travel by train to the capital city of Lisbon, set on seven hills at the mouth of the Tejo River. After lunch, climb the steep cobblestoned streets of the historic Alfama district, explore multicultural Mouraria, and take in the view from the ramparts of São Jorge Castle—a Moorish stronghold that presides over the city. (4–5 miles hiking, 4–5 hours)
Follow the Atlantic coast from Lisbon to the small village of Almoçageme. This is the starting point for our coastal hike to Cabo da Roca—the westernmost point of continental Europe. From the picturesque village of Almoçageme we’ll cross a small forest to reach the cliffs overlooking the Praia Grande (or big beach) and Praia da Adraga (Adraga Beach). From this point we continue up to the cliff tops, passing secluded coves and valleys on the way to the Cabo da Roca lighthouse. Our home for the night is the historic town of Sintra, nestled amid lush hills at the edge of a vast nature reserve that stretches all the way to the coast. (5 miles hiking, 5–6 hours)
Beautiful Sintra was a favorite haunt of Lord Byron and European royalty, but the Celts and the Moors made it here first. Pastel churches and manor houses line the cobbled roads, and palaces and castles loom among the misty forests. Our hike today begins in the old town, where we'll pass landmarks such as Santa Maria Church and a former home of Hans Christian Andersen. Then ascend to the hilltop Castle of the Moors, whose serpentine stone ramparts twist along the ridge, offering a fantastic view of Sintra’s crown jewel: the Palacio da Pena, perched on a neighboring peak. Designed by King Fernando II, this 19th-century Romanticist castle is a whimsical patchwork of turrets and domes overlooking luxuriant gardens. Continue there on foot, exploring the park paths and touring the opulent palace interiors. Return to Lisbon for a final dinner together tonight. (4–5 miles hiking, 5–6 hours)
After breakfast, transfer to the airport for your flight home.