Portugal: Coastal Walks & Douro Valley Vineyards

Arrive in Lisbon and check into Hotel Dos Reis Lisbon. The evening begins with a walk through two of the city's historic neighborhoods, offering a quiet introduction to the local culinary landscape. The route winds away from the main tourist thoroughfares, leading to traditional shops and local taverns. This evening walk focuses on regional food and wine, with stops at these neighborhood taverns for dinner, providing an immediate connection to the city's food culture.

The morning begins with a drive to Cabo da Roca, the westernmost point of continental Europe. From here, a 4km coastal trail traces the cliff edge, passing the viewpoints of Pedra de Alvidrar and Buraco do Fojo before descending to the stone arches and caves of Praia da Adraga. The terrain is technical in places, with steep sections requiring proper footwear. After the hike, the afternoon is spent exploring the botanical gardens and romanticist architecture of Palácio Monserrate in Sintra. The evening is free to explore Lisbon at your own pace.

Leave the capital behind for a four-hour overland journey east into the Beira Baixa province, toward the Spanish border. The destination is Idanha-a-Velha, one of Portugal’s designated historic villages, where you'll stop for lunch at a local restaurant. A moderate 3km walk follows, tracing a path through the countryside to a notable Ichnofossil site. The day ends with a short drive to the quiet rural town of Medelim, and the hotel that serves as the base for the next two nights.

Today’s walk focuses on Monsanto, a fortress village famous for its houses built directly into and under giant granite boulders. A short transfer leads to Relva, the starting point for a 4km hike that follows a segment of the GR7 E12 long-distance trail. The path ascends gently through a landscape of orange, fig, and olive trees before reaching Monsanto itself. A local guide leads a walk through the winding cobblestone streets up to the castle ruins, which offer commanding views of the plains below. The walk then descends to Carroqueiro, with the rest of the afternoon free back at the hotel.

The day is spent exploring two more of Portugal's historic villages. First is Sortelha, where a medieval castle sits on a formidable crag at 760 meters, its walls enclosing a maze of granite houses that feel preserved in time. From there, the route continues to Belmonte, a hilltop town best known as the birthplace of navigator Pedro Álvares Cabral. After exploring the town, the journey continues upward, climbing into the Serra da Estrela mountains to check into the Casa das Penhas Douradas, a design-led hotel set high in the range.

Spend the morning in the high country of Serra da Estrela Natural Park, the highest mountain range in continental Portugal. A 6km hike crosses the valley of Corgo das Mós, a landscape of rolling green hills punctuated by striking granite tors. The trail leads to the Vale do Rossim Lagoon, a reservoir set among the peaks. After lunch, a 200km overland transfer takes you north, descending from the mountains to the town of Amarante. The hotel for the next three nights, Casa das Lérias, is a converted monastery on the banks of the Tâmega River.

The day begins with a visit to the Casa de Mateus, the 18th-century baroque palace whose facade is recognizable from millions of wine labels. A guided tour explores the house museum and chapel before a glass of wine from the estate. From there, the focus shifts to Vinho Verde, with a visit to a family-owned winery in the region. A walk through the estate’s vineyards is followed by a regional lunch, paired with the local wines and views of the surrounding landscape. The evening is spent back in Amarante.

A 70km drive leads to Pinhão, a small town at the heart of the port wine-producing region. Today's hike is a more demanding 8km route with a 400-meter elevation gain, climbing directly through the steep, terraced vineyards that define this UNESCO World Heritage landscape. The trail ascends toward the village of Casal de Loivos, where a detour leads to a viewpoint with one of the region's most celebrated panoramas over the Douro River. After the nearly four-hour walk, the drive returns to Amarante, leaving the afternoon and evening free.

A morning drive brings you from Amarante to Porto, Portugal’s second city. After checking into the Pousada do Porto, a hotel set in a historic building on Rua das Flores, the afternoon offers a choice. Option one is a guided walking tour through the medieval streets of the Ribeira, Baixa, and Miragaia districts, with a stop at a local market. Option two is a cruise along the Douro on a traditional rabelo boat, followed by a walk across the river to Vila Nova de Gaia for a port tasting at Porto Augusto. The day concludes with a final dinner.

The itinerary concludes this morning in Porto. There are no activities planned, allowing for a final breakfast at the hotel before packing out and departing at your convenience for the airport or onward travel.