Revel in the Vinous History and Antiquities of Douro Valley, Portugal

To truly understand the Douro Valley’s wines and the sense of place they convey, you just have to visit. With thousands of years of art, culture and winemaking history, its gorgeous layers would take a lifetime to peel back. Assuming you only have a few days for discovery, however, start in lively Porto and wind past Port houses, vineyards and tiny villages so rustic you might believe that you’ve passed through time.

Traces of Porto’s roots reveal themselves at every turn. The hillside city above the mouth of the Douro was conceived more than 2,000 years ago. In 1996, Porto’s center became a UNESCO World Heritage Site.

Set the trip’s tone with a stately room in the renovated manor house Vila Foz Hotel & Spa. Downtown, relax at lively cafés and sip hard-to-find Portuguese labels in riverfront wine bars.

Firmly on the tourist circuit, century-plus-old Livraria Lello bookshop deserves a visit. Snap pics of the Baroque-inspired Clérigos Tower, an emblem of the city. Cross the iconic Dom Luís I Bridge to Vila Nova de Gaia, home to Port house row.

Tour Sandeman, which was founded in 1797, and its excellent museum, and conclude with a taste of current releases. Nearby, the 140-year-old Ramos Pinto offers tours of the cellar and its museum as well as tastings. Catch the train and enjoy breathtaking views of Douro’s legendary terraces as you head to Peso da Régua, the heart of wine country. There, visit the Museu do Douro to learn about wine production in the permanent exhibition, “Memory of the Wine Region.”

For sommelier-led winery visits, let the concierge at Six Senses Douro Valley organize your program. Management regularly devises itineraries that can include transportation, which eliminates the need to drive along twisted roads. A favorite is the “Travel Back in Time” tour, which starts at the archaeological site of Freixo-Tongobriga, an ancient Roman city, stops at a traditional restaurant for a wine-soaked lunch and finishes with an afternoon of Baroque architecture. The “Historical Villages” tour, meanwhile, takes guests via Tesla to excavated and restored villages and monasteries, and finishes with a traditional Portuguese cooking class in an 18th-century quinta.

Deep in the Upper Douro region, hike or kayak an open-air rock art collection that dates 25,000 years. Filled with Paleolithic and Iron Age engravings, the Vale do Côa Archaeological Park and Museum earned the Douro another UNESCO designation. Pre-arrange lunch with wine pairings at Ramos Pinto’s Quinta de Ervamoira. There’s a small museum devoted to the property’s history and unearthed antiquities.

Surrounded by organic vineyards and wildflowers, Casa do Rio supplies stylish dining and accommodation to this remote area. A sister to Quinta do Vallado, sip on estate wines while you contemplate the historical riches of the Douro Valley. —Lauren Mowery