Sintra

While Europe lays claim to many storybook scenes of beauty, it’s in Sintra that travelers truly step into a fairytale. Built amid (and into) the densely forested Serra de Sintra mountain chain, this resort town and UNESCO World Heritage Site offers a vivid assortment of bright and decadent architectural styles. Sintra’s three main castles allow visitors a chance to follow the town’s history. Begin with the commanding eighth-century granite turrets of the Moorish Castle, before moving on to Sintra National Palace, where you'll behold an eleventh-century collection of gleaming white design known affectionately among locals as “Town Palace.” And then it’s on to the magical Park and National Palace of Pena: Built by King Ferdinand II in the 19th century, he requested that the building and grounds resemble the set of an opera. With winding paths and series of color-drenched spires, the Pena complex is now the town’s dramatic crowning feature.

Explore Sintra with O.A.T. on:

• Back Roads of Iberia: Spanish Paradores & Portuguese Pousadas
• Gems of Western Europe: Lisbon to London
• Iberian Voyage: Lisbon to Barcelona
• Post Trip:Lisbon, Portugal on Northern Spain & Portugal: Pilgrimage into the Past

Evora

Perched on a hill and a hub for bustling trade routes, the town of Évora was coveted and controlled by the Celts, Romans, and Moors over the course of its storied history. Today a UNESCO World Heritage site, this walled city showcases this complex and layered history through its assortment of ruins and historical architecture. The influence of Rome is on clear display at the Temple of Diane, where 14 magnificent Corinthian columns date back to the second and third centuries A.D., and at the Romanesque-meets-Gothic É ora Cathedral. While the town bustles with the energy of a lively university population, its Church of St. Francis also offers a unique—and eerie—message to those who enter its Capela dos Ossos (bone cathedral): “We bones in here wait for yours to join us.”

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• Back Roads of Iberia: Spanish Paradores & Portuguese Pousadas

Alto Douro Wine Region

Along the upper stretches of the tranquil Douro River, vibrant terraced vineyards climb up the undulating hills of its namesake valley. Protected by the Marao Mountains from Atlantic breezes and home to nutrient-rich soil, historians estimate that wine has been produced here for more than two millennia, but became a sensation much later. In 1678, Englishmen returned from a visit to the Abbot of Lemago with a shipment of red wine fortified with brandy. The port made in the region became so highly coveted—and copied—that it became formally protected with a Designation of Origin to control the quality less than a century later. Today, this region continues to perfect its wine-making techniques, combining cutting-edge advancement with the time-honed traditions that earned its reputation. A UNESCO World Heritage Site, its contributions to viticulture—as well as striking natural beauty, sprinkled with centuries-old olive groves—continue to captivate visitors today.

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• Northern Spain & Portugal: Pilgrimage into the Past

Porto

One of Europe’s oldest continuously inhabited cities, Porto has always been a key player for Portugal, launching countless vessels in the age of the great navigations and then acting as the epicenter of the port wine trade. The Ribiera, the oldest part of the city, still reveals glimpses of 2,000 years of history along its medieval streets, while architectural gems beckon throughout the entire city, from the Neoclassical Palácio da Bolsa to the ornately Gothic São Francisco. Whether ducking into the country’s oldest bookstore, the 19th-century Livraria Lello, or marveling at the beauty of the Iberian Peninsula’s largest synagogue, visitors often find that Porto’s allure remains undimmed by time.

Explore Porto with O.A.T. on:

• Northern Spain & Portugal: Pilgrimage into the Past
• Gems of Western Europe: Lisbon to London
• Pre Trip:Porto: Northern Portugal’s Romanesque Gem on Back Roads of Iberia: Spanish Paradores & Portuguese Pousadas

Minho Province

Nestled between the Duoro and Minho rivers, Portugal's northernmost region was greatly influenced by the Celts and Romans who controlled it centuries ago, but for the Portuguese today, the region is known as the cradle of their nation's identity. The ninth-century city of Guimarães was also the site of 1128's Battle of São Mamede, which resulted in the Kingdom of Portugal's creation, and the establishment of its first capital city. Walking the streets of Guimarães' historic town center (a UNESCO World Heritage Site) today offers a glimpse into how this former medieval settlement developed over the years into a bustling modern town. Nearby Braga, Portugal's third-largest city, also proudly displays its historical and religious significance: Home to one of the world's oldest Catholic archdioceses and the hilltop pilgrimage site of Bom Jesus do Monte, Braga is known for the dramatic festivals it hosts throughout the year.

That said, this region also continues to generate buzz around food and wine enthusiasts: Minho's temperate climate is particularly well suited for agriculture, and has developed a sparkling reputation for its vinho verde. Directly translated to "green wine," the wine utilizes young grapes (whether red, white, or otherwise) and an early bottling technique to produce a unique and slightly fizzy mouthfeel.

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• Northern Spain & Portugal: Pilgrimage into the Past

Lisbon

More than 2,000 years ago, Romans told tales of Lisbon, the city of seven hills rumored to have been founded by Odysseus during his journey home from Troy. Over the millennia, Portugal’s now-capital city was transformed by its myriad settlers—among them the Greeks, Romans, Moors, and Christians. Yet it was the late 15th century that most dramatically shaped Lisbon’s place on the world stage. As Portugal’s Prince Henry the Navigator ushered in the Age of Discovery, maritime explorers set off for Western Africa and the far shores of the Atlantic. As many returned with tales, new wares, and lucrative trade routes, Lisbon became the hub of European trade and commerce. Signs of Lisbon’s past dominance are sprinkled throughout the city today—among them the Gothic Jeronmios Monastery and mighty Castelo de Sao Jorge fortress—but the city was devastated after three major earthquakes and a tsunami wiped out as much as a third of the city’s population in November 1755. That said, the lisboetas persevered, rebuilding their city and maintaining the lively spirit and love of life—food, wine, and traditional fado music that visitors can experience as they explore the lively Belem district and other city neighborhoods..

Explore Lisbon with O.A.T. on:

• Back Roads of Iberia: Spanish Paradores & Portuguese Pousadas
• Northern Spain & Portugal: Pilgrimage into the Past
• Iberian Voyage: Lisbon to Barcelona