Start your trip in Salamanca, a city that moves to the rhythm of the flamenco • Fuel up with tomato toast and Spanish tortilla before wandering through the dehesa, the pastoral oak woodland of central Spain where Iberian ham is raised free-range by swineherds • Get your first sight of the Douro River Valley and the Portuguese border from the trail • Taste locally grown almonds in the castle of Castelo Rodrigo village • Climb to a hilltop sanctuary with grand views over the surrounding serra. 

Welcome to Vinho Verde wine country • Zigzag along footpaths through steep vineyards that overlook the Douro River far below • Pair house wines with a colorful picnic spread at a quinta by the river • Stroll the cobbled, gaslit lanes of Pinhão, a wine country town lined with whitewashed arches and tile walls • Get a behind-the-scenes winery tour • Climb and descend from viewpoint to viewpoint in this steep country of terraced hills where vines cascade to the river. 

Journey high into the granite mountains to the north of the Douro River Valley • Hike between massive boulders and by ancient mills to a hidden shrine to St. James • Stop at a stone cottage in the forest for a taste of Portuguese mountain cuisine, with its emphasis on farm-to-table ingredients and incredibly tender meat grilled over coals • Listen to the fado, Portugal’s haunting and soulful national folk music • Hike through lush woods of cork, chestnut and eucalyptus trees between the aldeias do xisto (schist villages), made of stone fragments from the surrounding mountainside • Enter Porto the way wine merchants from upriver have for hundreds of years: cruising on traditional small boats. 

Explore Porto with a local guide who brings the city’s colorful World Heritage center to life • Head to the fishermen’s quarter for a fresh seafood lunch at a humble tavern • Stroll along the Atlantic or take some time to wander Porto on your own • Toast the end of our journey at a favorite restaurant in town.