If you’re driving from Porto, take the fast route, via Vila Real, and stop at Casa de Mateus, an ornate 18th-century Baroque palace with spectacular gardens. Check in to Six Senses Douro Valley, the region’s first full-service resort, outside the town of Peso da Regua. What the retrofitted 19th-century quinta might lack in views (Regua is not the region’s loveliest town) it more than makes up for with supremely comfortable rooms, an excellent spa, and activities like forest hikes, yoga, and movies under the stars.
After a leisurely morning at the spa, head out for lunch at DOC, from top Portuguese chef Rui Paula—try his pork neck, which he cooks for 12 hours and serves with a creamy celery puree. Then it’s time for wine tastings. The Douro still cultivates much of its grapes for port, but since 2003 five winemakers known as the Douro Boys have greatly advanced the region’s red and white wine production. Spend the afternoon at two of their wineries: Quinta do Vallado and Quinta do Crasto.
Get out on the water and take a river cruise aboard a restored 1950s wooden boat with Pipadouro. After you’ve docked back in Pinhao, have a picnic and port-wine tasting at Quintado Bomfim, a Symington family vineyard that produces grapes for Dow’s Port. Then, two options: head back to the Six Senses or book yourself into Casa do Rio, a six-suite contemporary hotel in the remote Upper Douro on Quinta do Valla do’s other estate, Quinta do Orgal.