From a Roman colony and centuries of Moorish rule to the great explorers of the Age of Discovery, Spain and Portugal are home to extraordinary beauty and untold remnants of a tumultuous past. We’ll chart our own course for discovery in these ancient lands while staying in intimate Portuguese pousadas and Spanish paradores, restored historic inns—from castles and convents to manor homes and monasteries—that evoke the glory of an earlier era. We'’ll also dine with a Spanish family in their home, tour a Portuguese vineyard and wine estate, and learn about the history of bullfighting at a finca ranch in Ronda, a medieval town perched high above a plunging gorge. Discover royal cities, hilltop citadels, and ancient olive groves—on a journey deep into the lands of conquerors and conquistadores.
5 nights from only $1495
From the time of the Romans and the Celts, Northern Portugal has been a hotbed of rich culture and robust vintages. Discover the role of vineyards in Porto's history during visits to a family farm and a wine cellar. As we stroll the lanes of the Ribeira neighborhood, follow the contours of the Douro River, or ascend in a cable car from nearby Gaia, we’ll get to know this ancient gem from many angles.View Extension Itinerary
You depart today on your overnight flight from the U.S. to Lisbon, Portugal.
After an overnight flight, arrive at the airport in Lisbon, where an O.A.T. representative will greet you. After a brief orientation walk to gain familiarity with our surroundings, we’ll enjoy a Welcome Drink and a briefing about our upcoming discoveries at our hotel. We’ll also meet those who traveled on our optional Porto: Northern Portugal’s Romanesque Gem extension. This evening, our group will gather for dinner at a local restaurant.
After breakfast, we set out for a discovery of Lisbon. Spread out on seven low hills overlooking the Tagus River, the legendary Portuguese capital has lured traders and settlers for more than 20 centuries.
In the late 15th century, the port of Lisbon was the staging point for Portuguese explorations that would usher in the great Age of Discovery—and make Lisbon the richest European capital until the 19th century. Highlights of our panoramic city tour include Belém, a neighborhood that is home to a variety of cafés, museums, gardens, and parks, as well as two UNESCO World Heritage Sites dating from the early 16th century: Belém Tower and Jerónimos Monastery. At Jerónimos, which was built as a monument to celebrate Portuguese voyages around the world, we'll visit the monastery's church, whose lower choir is the resting place of Vasco da Gama. Jerónimos is considered a jewel of Manueline architecture (named after King Manuel I), a flamboyant building style that glorifies Portugal's seafaring past. In Belém, we'll also view Lisbon's iconic Monument to the Discoveries, where Portugal's intrepid explorers are immortalized in sculpture. Then, we'll drive through Baixa, an area in the heart of Lisbon that was destroyed and completely rebuilt after the Great Earthquake of 1755. Baixa now features broad squares and avenues flanked by shops, cafés, and elegant Neo-Classical buildings.
Later, we'll leave the city's environs to visit Sintra, a village situated within a fairytale landscape of lush forests, turreted palaces, and castle ruins. Our discoveries include Pena Palace, a lavish 19th-century hilltop castle built on the ruins of an ancient monastery. After a walking tour through the palatial gardens of this UNESCO World Heritage Site, we'll return to Lisbon. Tonight, we'll head to a local restaurant for dinner and a private performance of Portugal's traditional melancholic style of music known as fado.
Today, we'll journey south of the city to a region of farmland and fields and focus on some of Portugal's popular rural traditions. Our discoveries include a visit to a traditional artisanal cheese producer to learn about Azeitão cheese, a velvety local specialty made from raw sheep's milk. Then, after lunch at a local restaurant, we'll learn about another longstanding Portuguese tradition: azulejos. Introduced to Iberia by Moors, these blue or multi-colored ceramic tiles decorate everything from church walls and palaces to the façades of most Portuguese homes. We'll also gain insight into the ancient art form of azulejos by trying our hand at painting some of the tiles.
We return to our hotel in Lisbon in the late afternoon. Dinner is on your own this evening.
After breakfast, we depart Lisbon and journey through the unspoiled wine-growing region of Alentejo province on our way to Évora. Our route is through gently rolling terrain, which is dotted with vineyards, cork trees, olive groves—even several prehistoric monuments. To break up our journey, we'll stop in Arraiolos, a small village near Évora that is renowned throughout the world for its hand-embroidered wool carpets and tapestries. Here, we'll learn about the centuries-old rug-making techniques. Then, we'll learn about Portuguese wine at a traditional 18th-century monte (a typical Alentejo farming estate), where we'll tour the vineyard, winery, and cellars. We'll also get to sample a few of the estate's wines and enjoy an included lunch.
Later this afternoon, we'll arrive in Évora and enjoy an included dinner at our historic pousada.
This morning features a walking tour of Évora, an ancient hilltop town with Roman and Moorish roots that is a UNESCO World Heritage Site. Our stroll within Evora's medieval walls will reveal a series of whitewashed houses adorned with wrought-iron balconies. We'll also see the influence of Rome at the ruins of the Temple of Diana, whose 14 exquisite Corinthian columns date back to the second and third centuries. Next to the Roman temple is the equally imposing Évora Cathedral, a rose granite monument blending Romanesque and Gothic architecture, with some of its most ancient sections dating from the beginning of the 13th century.
Near Évora's main square is the Church of St. Francis, home to a macabre bone chapel (Capela dos Ossos) which welcomes visitors with the eerie message: “We bones in here wait for yours to join us.” Inside, thousands of skeletons and skulls have been carefully arranged along the chapel walls, ceilings, and columns—put there by three Franciscan monks in the early 16th century who wanted wealthy residents of Évora to reflect on the transience of material things and inevitability of death.
During lunch on your own, you may wish to pick up a regional specialty like smoky paio sausage or Serpa cheese to go along with freshly baked bread for a simple and delicious meal. Then, the remainder of the afternoon is yours to stroll along the cobbled streets of the town that many of the 15th-century Portuguese kings once called home.
This evening, we'll gather together to learn some of the secrets of Portuguese cuisine during a cooking lesson, followed by an included dinner.
Crossing into Spain today, we enter Extremadura, an autonomous Spanish province known as the homeland of such famous 16th-century conquistadores as Pizarro and Cortés. As we traverse this vast and sparsely populated farming region we will likely see views of storks nesting in ancient steeples and medieval towns dotting the plain. Although Extremadura once marked the boundary between Moorish and Christian Spain, the capital of the region, Mérida, fell under Moorish, Christian, and even Portuguese control throughout its storied history. It is better known, however, as one of the most famous Roman capitals on the Iberian Peninsula, and it displays this heritage in some of the best-preserved Roman ruins in all of Europe. Today, we’ll explore the UNESCO World Heritage Site of Mérida, including its 6,000-seat Roman theater and the adjoining amphitheater, where gladiators once battled to the death against animals imported from Asia and Africa and confined in the large, cross-shaped pit we’ll see at center stage.
After lunch on your own, we continue our journey to the charming Andalusian town of Carmona, arriving in time for an included dinner at our lodgings in one of Spain’s historic paradores.
Spend the day exploring Carmona on your own, or join an optional tour to Seville, the romantic Spanish city renowned for bullfighting, the flamenco, and Don Juan. This optional tour reveals several of Seville's highlights, including its picturesque whitewashed homes, 2000-year-old plazas, and maze of cobbled streets in neighborhoods like the Barrio de Santa Cruz. We'll also explore the Seville Cathedral, one of the largest and most impressive churches in the world. Built in the 15th century at the site of a 12th century mosque, the massive Cathedral is also home to the golden Retablo Mayor, the largest altarpiece in the world—and is the reputed burial place of Christopher Columbus.
Travelers staying in Carmona will also enjoy exploring this picturesque walled town with its Roman-era streets at their own pace. You'll want to see the Seville Gate and its double Moorish arch, which leads to the narrow streets, whitewashed walls, and Renaissance mansions of Old Town. Cozy Plaza San Fernando is home to a series of elegant 17th-century homes; and the nearby Roman Necropolis contains the relics of more than 900 families that lived in and around Carmona some 2,000 years ago.
This evening, our small group will gather for an included dinner featuring authentic tapas—an essential part of Spanish life—at a local restaurant.
Please note: If Day 8 falls on a Sunday, we will visit the walled fortress of El Alcázar instead of the Seville Cathedral.
Today we journey south from Carmona to Ronda, admiring views of several of the region's famous “white villages” along the way. Nestled into mountainsides or set atop dramatic gorges, Andalusia's Pueblos Blancos are a series of picturesque whitewashed hill towns and quaint villages that also offer a glimpse of Spanish life and culture during medieval times. Our destination, Ronda, is actually one of the largest—and most spectacular—of Andalusia's white hill towns. But to Spaniards, Ronda is far more famous as being the birthplace of modern bullfighting. Before our arrival Ronda, we'll stop at a bull ranch owned by a famous bullfighter to learn about this way of life and the breeding of toros. Then, we'll enjoy a traditional lunch.
We arrive in Ronda in the afternoon, where you will have free time to explore and relax before dinner at our parador, Ronda's historic town hall.
Few places are able to boast a more dramatic setting than Ronda, one of the oldest cities in Spain and a one-time stronghold for legendary Andalusian bandits from the 18th to early 20th centuries. Ronda is divided by a 360-foot-deep ravine—El Tajo—which is spanned by three bridges, including the newer Puente Nuevo, a graceful 18th-century stone structure high above the Guadalevín River. On one side of the 210-foot-wide gorge are the narrow medieval streets of Ronda's Moorish Old Town, known as La Ciudad; on the other, the more recent El Mercadillo quarter, which was constructed after the Christian Reconquest of 1485. Homes clinging precariously to the cliff faces of El Tajo add even more to Ronda's dramatic beauty. Our full-day walking tour will focus on Ronda's walled Old Town, where we'll wander through its labyrinth of medieval streets, flanked by Moorish whitewashed homes with wrought-iron balconies.
We'll pause for an included lunch during our tour, and also enjoy the spectacular views of the canyon from atop the Puente Nuevo Bridge, with the valleys and hills shimmering in the distance. Just don't get too close—in his novel For Whom the Bell Tolls, Ernest Hemingway describes how prisoners were tossed alive from this very spot into the deep gorge below during the bitter Spanish Civil War. Hemingway also famously wrote about bullfighting, and Ronda is home to one of Spain's oldest bullrings. Built in 1785, the Plaza de Toros is where cavalry training consisting of spearing bulls from horseback developed into the more “sporting” form of confronting the bull on foot. The father of this modern form of bullfighting was Ronda native Francisco Romero, and his grandson Pedro is widely considered the most famous Spanish bullfighter of all time (the matador is said to have killed almost 6,000 bulls here during his long career). Pedro Romero is also immortalized by Hemingway in his novel The Sun Also Rises. After lunch, we'll enjoy some time at leisure.
Dinner is on your own this evening.
After breakfast at our parador, we'll depart Ronda and journey to Úbeda. En route, we'll enjoy an included lunch at a local restaurant before a visit to the city of Córdoba. While it was originally founded as a Roman colony, Córdoba reached its peak as an Islamic capital in the tenth century, rising to become the largest (and arguably, most multicultural) city in Western Europe. Today, Córdoba is known primarily for Mezquita, its mesmerizing eighth-century mosque and one of the world’s greatest Islamic buildings. But what makes this mosque truly unusual is Capilla Mayor, a Gothic Christian church built in the center of the mosque in the 16th century by Charles V. Today, mass is still celebrated here daily. We’ll explore Mezquita and enjoy a horse-drawn carriage ride through the streets of Córdoba before continuing on to Úbeda.
Upon arrival, we'll enjoy an included dinner at our parador, conveniently situated in the town's Renaissance-era main square, a UNESCO World Heritage Site.
We begin the day with breakfast at a traditional café in Úbeda's neighboring town of Baeza, followed by a walk to admire some of the monuments of this compact Renaissance gem. Afterwards, we'll discover another highlight of the region—olive oil. Situated in Jaén province on a plateau between the Guadalquivir and Guadalimar rivers, Úbeda is bordered on all sides by numerous olive groves that produce some of the world's best olive oil. We'll learn about the olive oil production process—from harvesting to bottling—beginning with a walk through a stand of olive trees, followed by a discovery of traditional and modern olive-oil production at one of the many local mills where we'll sample some of the flavorful Esencial Olive extra virgin olive oil. Then, we'll meet with members of Proyecto Ilusion, a volunteer organization that helps disabled individuals—and is supported by Grand Circle Foundation. Parents in the local community cherish the ongoing efforts of this organization, as Proyecto Ilusion has helped many of their children develop social skills to improve their lives. After that, we'll split into smaller groups to enjoy some authentic Andalusian hospitality during a Home-Hosted Lunch with some local families engaged in the olive-oil industry.
We then return to Úbeda, an ancient provincial city often referred to as the “Florence of Andalusia.” At Casco Antiguo (Old Town), we'll wander the narrow cobblestone streets lined with Renaissance-era palaces, stately mansions, and tile-roofed whitewashed homes, centered around the Gothic church Iglesia de San Pablo. With dinner on your own this evening, you may wish to work up an appetite exploring a few of Úbeda's famous leather and pottery craft workshops before trying out a local restaurant.
Today, we depart Úbeda for Madrid, stopping en route to explore Toledo. After lunch at a local restaurant, we'll arrive in Toledo, former Spanish capital—still capital of the autonomous province of Castile-La Mancha—and a beautifully preserved medieval gem. Perched on a hill overlooking the Tagus River in the heart of Spain, Toledo was known as the “city of three cultures” for its harmonious blend of Christian, Jewish, and Muslim cultures from the 11th to the 13th centuries.
We'll embark on an afternoon walking tour of this 2,000-year-old UNESCO World Heritage Site, which Don Quixote author Miguel Cervantes described as the “glory of Spain and light of her cities.” (Please note: If the cathedral is closed, we will only be able to view its exterior). We'll also see the Church of Santo Tomé.
Upon arrival at our hotel in Madrid in the early evening, dinner is on your own.
Contrast Spain's former capital city with its modern one as we explore Madrid this morning. Highlights include stops at bustling Plaza de España; the opulent Palacio Real (Royal Palace); and Templo de Debod, an ancient Egyptian temple given to Spain in 1968.
Lunch is on your own followed by an afternoon at leisure. Or, you may wish to join our optional tour to the beautiful medieval town of Segovia, a UNESCO World Heritage Site that is home to an ancient Roman aqueduct and the famous hilltop castle of Alcazar.
Dinner is on your own this evening.
After breakfast, enjoy a day at leisure in Madrid. You may wish to join your Trip Leader on a discovery walking tour of the city, or strike out on your own to mingle with the madrileños along the lively boulevards and plazas, browse one of the city's renowned museums, such as the Prado; or discover why the Spanish say, “De Madrid al cielo” (Madrid is the next best thing to heaven) in one of the city's lovely parks.
This evening, our small group will celebrate our two weeks of Iberian discoveries during a festive Farewell Dinner accompanied by a flamenco performance at a local restaurant.
After breakfast, we depart for the airport for our return flights home, or to begin our post-trip extension to Bilbao & Spain’s Northern Coast.
7 nights from only $2695
Discover the beauty and culture of Northern Spain, from the Basque gem of Bilbao to historic Santander on the Bay of Biscay. Then explore Orviedo, the heart of Asturias. With included tours, visits to medieval villages, and time to explore on your own, you’ll enjoy a rich array of perspectives on three of Spain’s most fascinating cities.View Extension Itinerary