We’ll begin the day at Seville’s Cathedral—once a mosque, later transformed into the largest Gothic cathedral in the world. Here we'll examine Spain’s imperial rise and its ideological foundations. We’ll pause in the Chapel of the Sailors (Capilla de los Navegantes), where Columbus is believed to have given thanks after his return from the Americas, and where generations of explorers prayed before departing for the New World.

It was from this very city that Spain declared Plus Ultra—a vision of empire that refused the old motto Non Plus Ultra, “Nothing further beyond.” In Seville, Spain claimed that the end of the world was only the beginning.

In the evening, we'll share a tapas crawl and sherry tasting that reflects Spain’s shifting social fabric—culinary traditions with Moorish and Jewish roots adapted in a post-Inquisition world.

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Meals: Breakfast and Dinner included
Walking: ~2 hours
Accomodation: Tayko Hotel

After breakfast this morning, we'll travel to Córdoba, once a center of Islamic learning and culture. At the Mezquita-Cathedral, we'll encounter not only a building, but two radically different ways of understanding divine presence. The original mosque, with its forest of columns and geometric repetition, was built to evoke humility and transcendence—not through images or altars, but through space, rhythm, and light. It invited worshipers to dissolve the ego and encounter the divine in stillness and order.

Centuries later, Christian rulers inserted a Renaissance cathedral into the heart of this sacred geometry. Their goal was not erasure, but elevation—a desire to match, or perhaps surpass, the beauty they inherited with their own symbols of triumph and faith in the incarnate word. The resulting building is a powerful expression of Spain itself: layered, complex, contradictory, and astonishing. 

In the afternoon, we'll continue to Molino del Conde, a restored countryside estate that offers quiet contrast to the imperial cities.

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Meals: Breakfast and Dinner included
Walking: ~2 hours
Bus Time: ~4.5 hours total (2 hrs to Córdoba, 2.5 hrs to Molino)
Accomodation: Molino del Conde

Today we'll visit the olive farm and country house of Manuel Quintana, a multigenerational farmer and founder of Moltura—a family-run project dedicated to traditional cultivation and sustainable practices. As we walk through his groves, we’ll learn to distinguish between olive varieties and explore the rhythms of a life shaped by the land.

Manuel and his wife will then welcome us into their country home for a traditional paella meal, prepared with their own olive oils and local ingredients. This intimate gathering offers not only a taste of Andalusia, but a window into the values and hospitality that define its rural culture.

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Meals: Breakfast, Lunch, and Dinner included
Walking: Light
Accomodation: Molino del Conde

We'll begin with a visit to the Alhambra and Nasrid Palaces—among the most astonishing architectural and engineering achievements of medieval Europe. Designed for spiritual contemplation and political power, the Alhambra fuses Islamic geometry, poetry, water engineering, and aesthetic restraint into a vision of paradise on earth. Its symmetry, flowing water, and carved epigraphy reflect a cosmos governed by divine order—made manifest in stone, space, and sound.

After free time for lunch, we'll regroup to visit the Royal Chapel of Granada, where Ferdinand and Isabella—the Catholic Monarchs—chose to be buried. Their decision to be interred here, rather than in Seville, Toledo, or Valladolid, was symbolic. Granada marked the culmination of the Reconquista—the fulfillment of a Christian vision of unity. From here, they funded Columbus’s 1492 voyage, hoping not only to reach Asia but to find lost Christian allies and prepare for a new crusade.

We'll see that Granada, in this sense, was both an ending and a beginning: the close of Muslim rule in Iberia and the launch point of a global Catholic empire.

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Meals: Breakfast and Dinner included
Walking: ~3 hours
Bus Time: ~3 hours (1.5 hrs each way)
Accomodation: Molino del Conde

We'll travel north to Trujillo, birthplace of many conquistadors. Upon arrival, we’ll take a walking tour through the town’s historic center, including its medieval castle, the museum, and the central plaza dominated by the statue of Francisco Pizarro.

This quiet Extremaduran town gave rise to many of Spain’s most ambitious explorers—often the illegitimate sons of nobles, men with lineage but no fortune or future at home. With limited prospects in the dehesa, they set their sights on the riches of the New World, driven by a blend of faith, aspiration, and desperation.

In the afternoon, we'll choose from optional activities—birdwatching in the plains, visiting a blacksmith, exploring a local winery, or playing the town’s historic organ.

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Meals: Breakfast and Lunch included
Walking: Optional
Bus Time: ~4 hours
Accomodation: Parador Trujillo

A visit to a traditional pig farm will introduce us to the oak-covered dehesa ecosystem, a model of sustainable Iberian land used for over a thousand years. 

After a rustic lunch on the farm, we'll continue to Madrid, capital of Bourbon Spain and hub of modern political life. Arriving in the mid-afternoon, we'll check into our hotel located in the historic city center. You'll be free for the remainder of the day to explore the urban life of Madrid. Once a modest fortress town, it rose to prominence in the 16th century as the seat of Spain’s monarchy, evolving into a cultural powerhouse expressed in late-night plazas, cafes, political debate, and world-class museums. (Please let us know whether you'd like to visit the Prado museum on Oct 9 or 10)

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Meals: Breakfast and Lunch included
Walking: Light
Bus Time: ~4 hours
Accomodation: Catalonia las Cortes

We'll begin the day with a walking tour of central Madrid and a guided visit to the Royal Palace, examining how the Bourbons rebranded Spain after centuries of Habsburg rule. Built on the ruins of a moorish fortress, the Royal Palace is the largest royal residence in Western Europe and is an archetypal symbol of Spanish power and prestige. While exploring its frescoed halls, our local guide will walk us through centuries of its storied past, from Bourbon coronations to Francoist spectacles.

In the afternoon, you are free to visit the Prado, where imperial patronage produced some of Europe’s most iconic artworks.

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Meals: Breakfast included
Walking: ~3 hours
Bus Time: None
Accomodation: Catalonia las Cortes

We'll leave the Castilian plateau for La Rioja, stopping in Burgos—home of El Cid—for lunch. A medieval jewel in northern Spain, Burgos was the early capital of Castile and is a key stop on the Camino de Santiago. By afternoon we'll reach Briones and begin our wine-focused journey with a visit to Marqués de Riscal, where avant-garde design meets centuries-old wine tradition. After checking into our hotel in the late afternoon, and saving time for a brief siesta, we'll regroup for a delicious Riojan dinner.

Meals: Breakfast, Lunch, and Dinner included
Walking: Light
Bus Time: ~4 hours
Accomodation: Santa Maria Briones

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After breakfast this morning, for those who are interested, we'll dedicate the morning to joining in the spirit of the Camino de Santiago. Embracing the idea of travel as personal pilgrimage and a journey of self-transformation, we'll depart for Najera to visit the 11th‑century Monastery of Santa María la Real, the ancient rock-carved caves, and the castle ruins which share the experience of Rioja’s Camino corridor.

For those who wish to stay behind, a quiet morning in Briones offers an opportunity to rest and visit the Vivanco Wine Museum.

In the early afternoon, we'll regroup to explore Rioja’s calados—underground wine cellars—and its family-run vineyards. Keeping in this tradition, we'll visit a family run bodega and winery for dinner and vino.

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Meals: Breakfast, Lunch, and Dinner included
Walking: ~2–3 hours
Bus Time: ~1 hour total
Accomodation: Santa Maria Briones

After breakfast in our hotel, we'll explore the countryside of this region by electric bike, stopping at medieval bridges, riverside vineyards, and stone shelters built by past generations.

For lunch this afternoon, we'll participate in a tradition as ancient as human presence in the land. Pausing for a picnic of Spanish meats, cheeses, and breads, our lunch will reflect the relationship between place, sustenance, and continuous traditions.

We'll return to Briones by the early afternoon and our sprinter bus will be at your disposition to visit a Cumming family wishlist of wineries, or simply to return to Briones for a quiet afternoon.

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Meals: Breakfast and Lunch included
Walking/Biking: Moderate effort
Bus Time: None
Accomodation: Santa Maria Briones

Departing Rioja after breakfast, we'll travel to San Sebastián and take to the water—sailing or boating along the Basque coastline. Our planned stops will be contingent on the weather and plan to include a fishing village where we taste local cheese, cider, and salt cod while discussing Basque maritime culture and identity.

In the late-afternoon, we'll check into our hotel before heading out for a self-guided pintxos crawl in the Old Town with a chance to taste local classics ranging from anchovies and green olives to stuffed spider crab or seared foie gras. This evening we'll savor the city’s deep-rooted Basque identity through food, conversation, and fellowship with family.
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Meals: Breakfast, Lunch, and Dinner included
Walking: Light
Bus Time: ~2.5 hours
Accomodation: Hotel Arbaso

A final walking tour through San Sebastián will connect landscape, language, and identity in the Basque Country. From Mount Urgull to the port and La Concha Bay, we'll explore how this region has preserved autonomy through language, cuisine, and custom.

Our farewell dinner will celebrate the many Spains we’ve encountered—and the deeper connections now possible.

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‍Meals: Breakfast and Dinner included
Walking: ~2–3 hours
Bus Time: None
Accomodation: Hotel Arbaso

After breakfast, private transfers are arranged to Bilbao or Madrid. For those traveling through Bilbao, we'll make a stop at the Guggenheim museum on the way to the airport.

This isn’t the end of a trip, but the start of seeing Spain—and travel—through a new lens, one characterized by savoring family meals, traditions, and stories.

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Meals: Breakfast included
Bus Time: Varies depending on airport transfer