Experience the history and culture of port winemaking along the Douro River.

Pictured above is Porto, Portugal’s second-largest city with ancient, pastel-hued houses lining the riverfront, and slipperlike rabelo boats bobbing in the water. Venture down the city’s medieval cobblestoned streets and pop into the Palácio das Artes museum – followed naturally, with a glass of port.

Portugal was named after Porto, where port winemaking is embedded in the history and culture. Ideal for river cruises, we recommend wine lovers consider sailing through the Douro Valley, one of the world’s oldest wine regions.

As early as the fourth century, Romans cultivated wine in this harsh, rocky region. Its hot, arid climate was good for growing grapes, but not for storing wine, so casks were transported by boat to Porto, at the mouth of the river, where the wine was aged on the lower banks. Back then, the Douro was wild and unpredictable, and to keep the wine from spoiling along the journey, a little brandy was added – which is how port came to be. Today, thanks to a system of locks, the river is as calm as bathwater, ideal for river cruising.

Mateus Palace – Photo by Rachael A. Jones

About halfway to the Spanish border, is Pinhão in the heart of the Douro Valley’s wine-making region.

Learn about port-making at Quinta do Seixo, where some of the best and oldest grapes for the renowned Sandeman ports are grown. At the eighteenth-century baroque Mateus Palace in the nearby town of Vila Real, wander among the box hedges in its French-inspired gardens. Rather than its history, the palace is best known for its likeness, which appears on the label of the middlebrow Mateus rosé, still sold in its iconic World War I-inspired flask-shaped bottle.

A wine bar on the riverbank.  -EStock Photo

Barca d’Alva, the last Portuguese town before the Spanish border, and Régua, first settled by the Romans are beautiful towns to explore. Wine lovers won’t want to miss the tiny pre-Roman hilltop town of Favaios, where we recommend the family-owned Quinta da Avessada, where port is produced from a vineyard so ancient that it’s been designated a UNESCO World Heritage site, and the view reveals vineyard-covered Douro Valley hills as far as you can see.

Portugal is home to roughly 250 native grape varieties; wine is harvested, produced, and tossed back in nearly every corner of the country. In its capital, enjoy a variety of hotels and don’t miss Lisbon’s quiet Estrela neighborhood.

Advisor Tip

For a winetasting day trip from the city, We recommend Quinta de Sant’Ana, a family-run estate in the Sintra region less than 45 minutes north of Lisbon.

French Import: Les Bons Vivants

Owners Léonie Benoist and Ulysse Jasinsky modeled this shabby-chic boîte in up-and-coming Intendente on the easygoing French bistros they frequented while growing up in Poitiers. Redbrick walls, warm wood furniture, and neon signs set the scene for a night of French cheese and wine. The team imports les vins themselves, including only-here exclusives such as the Les Bons Vivants Cuvée, a fresh, fruity blend of muscadelle and sauvignon blanc, made in partnership with biodynamic winemaker Philippe Maffre in southern France. Benoist appreciates how low-intervention wines allow her to better connect with guests. “These are the types of wine that you need time to discuss with people,” she says. “They offer a surprise each time.”

Organic wines from Prado Mercearia.

Prado Mercearia

Timeworn, geometric-patterned tiled floors; mason jars filled with colorful ingredients; and antique reproductions that mimic old-world, buy-everything-here grocery stores make this gourmet deli-cum-wine bar one of Lisbon’s most photogenic spaces. Lining the shelves are Portuguese foodstuffs and wines, which visitors can purchase to go or enjoy at one of the smattering of tables. The all-natural, all-Portuguese wine list is ever-growing and ever-changing. “We’re seeing new producers emerge from different parts of the country all the time,” says grocer Carlos Duarte. “People are thirsty for them.” Duarte is a fan of the 2020 Loureiro from Aphros, a biodynamic farm in the northern region of Minho. Its aromatic sweetness is balanced by bracing acidity – just the pour to put a smile on a sunny Lisbon afternoon.