* Tavira: While much of the central Algarve coast has been scarred by mass tourism, the region’s eastern and western extremities retain their charm. Nowhere more so than this little town, where noble 17th-century homes line the riverside, narrow streets are filled with restaurants and cafes, and small boats can whisk you to near-deserted island beaches. 
* Óbidos: Clustered around its 12th-century castle, this is one of Portugal’s best-preserved medieval towns. Its maze of cobbled lanes connects whitewashed houses with bright blue or yellow trim. The town is also famed for its bookshops, its sweet cherry liqueur, and the white sands of its lagoon that opens out into the Atlantic nearby.
* Belmonte: Birthplace of the explorer who discovered Brazil and home to a Jewish community that preserved its faith in secret through centuries of persecution, Belmonte is built from granite hewn from the remote central highlands. Among the rough stone buildings are a 13th-century castle and the ruined tower dating back to Roman times. 
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* Amarante: Inland from Porto, Amarante sits on a tree-lined curve in the River Tâmega. Its Renaissance-style riverside church, built with Spanish and Italian influences out of soft golden local stone, is surrounded by townhouses rising up the hillside and spreading along the riverbank. It is home to a fine luxury hotel, a surprising museum of modern art, and famed cafes serving sweet almond- and cinnamon-flavored pastries.
* Marvão: As dramatic locations go, this could hardly be better. Marvão is perched on a rocky crag rising 860 meters (2,800 ft.) out of the Alentejo plain. It stood as a frontier post for centuries, fought over by Celts and Romans, Muslims and Christians, Castilians and Portuguese. Inside its medieval battlements, the old whitewashed town has survived all those battles. Views are extraordinary, especially if you’re there at dawn or sunset. 

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* Angra do Heroísmo: The history-packed capital of Terceira island in the Azores permits residents to choose from 18 authorized shades for painting their houses. The result is a riot of pastel facades huddled around a couple of Atlantic coves and framed by volcanic slopes covered in grass of the deepest green. The city was a key staging post for the Portuguese trading empire and served as an inspiration for colonial ports across Latin America.

* Miranda do Douro: Located on the edge of a canyon formed by the River Douro on Portugal’s northeast frontier, Miranda has been a land that time forgot since 1762, when invading Spaniards blew up a big part of it and the authorities decamped farther from the border. Isolation has allowed the town to maintain its own unique language, Mirandese, and traditions like the war dance performed by local men wearing frilly skirts and striped woolen socks. There’s a sturdy stone cathedral and cobbled streets lined with centuries-old homes. It’s also famed for steak. 
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* Piodão: Huddled on a terraced hillside in a remote corner of the Açor mountains in the center of the country, homes here are made from dark, almost black schist stone with slate roofs. In dramatic counterpoint is the little parish church, a wedding-cake confection in purest white with pale blue trim. At dusk, when the village glitters with yellow lights, it resembles a Neapolitan nativity scene. It’s a great base for hiking the hills or sampling hearty highland dishes like goat slow-cooked in red wine. 

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* Ponte de Lima: Once a Roman outpost, Ponte de Lima lays claim to being the oldest village in Portugal. It’s defined by the ancient stone bridge that arches over the slow-moving River Lima and connects the village to the slender tower of St. Anthony’s Church on the west bank. Ponte de Lima is packed with historic mansions whose balconies overflow with summer flowers. It’s set in the verdant hills of the Minho region and surrounded by baroque estates producing crisp vinho verde wines. 

* Mértola: Clinging to a high ridge over the River Guadiana, this picturesque collection of white-painted houses surrounded by medieval walls was the capital of an Arab kingdom in the Middle Ages. Its parish church was a mosque with a multi-columned interior—a rare survivor of Islamic architecture in Portugal. Wandering its ancient streets, it’s not hard to imagine its golden age as a cosmopolitan river port. The river provides swimming and kayaking opportunities, and local restaurants thrive on boar, hare, and other game hunted in the wild surroundings.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.