Old town Alcazar in Toledo, Spain

Spain Tour of Castles & Conquistadors

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Oropesa, Jarandilla de la Vera, Plasencia, Trujillo...

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Suggested Duration

12 Days

Spain's opulence radiates from the castles of its medieval walled towns. 16th century Conquistadors made this land the wealthiest in the world, leaving behind fabulous palaces and streets of historic intrigue. Relive the ancient splendor with this unique tour; sleep in converted castles, discover wonderful Roman relics, and immerse yourself in destinations perfectly preserved and unchanged. This is Spain at its most luxurious and medieval Europe at its most iconic.

Customizable Itinerary

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Trip Highlights

  • Discover the fabulous palaces and castles that were built with Conquistadors' wealth, including Palacio de Marquès de la Conquista and Palacio of Orellana-Pizarro
  • Explore the historic region of Extremadura, birthplace of Spain's famous conquistadors and the wealthiest place in the world during the 16th century
  • Relive history by staying in Spain's finest paradors, five-star luxury hotels nestled inside historic castles and monasteries
  • Enter through the walls of medieval Toledo and settle into the rhythm and grandeur of a forgotten era
  • Immerse yourself in the beauty of World Heritage Caceres, a city of exoticism and opulence since 13th century Moorish times
  • Step back further in time by exploring Roman Merida, home to some of the finest preserved Roman remains to be seen anywhere in the world
  • A few little touches showcase the rich diversity of the region, like VIP wine tasting, gala dinners, and some superb traditional tapas

Detailed Description

Spain's Conquistadors hailed from Extremadura, a land of kaleidoscopic mountain plateaus in the heart of the country. As they discovered the Americas they brought back impossible wealth to their homelands, filling it with golden palaces, charming castles, and walled towns built without thought of budget. Spain has moved on since these 16th century times. But the land of castles and Conquistadors remains perfectly preserved, an ode to medieval splendor and a canvas for escaping into a forgotten time. This unique tour explores one of Europe's most iconic and beautiful regions, connecting its ancient walled cities and reliving the grandeur of centuries past. It's a fully immersive itinerary; sleep in castles converted into luxury hotels, enjoy private tours of walled towns, and also discover an exotic history that existed before the Conquistadors. You won't just be traveling to the 16th century. Moorish architecture and Roman remains reveal a region of eclectic chronicles.

Spain's exclusive paradors are a highlight of this tour, starting with your welcome evening in the Castle of Oropesa of Toledo. Paradors are the country's historic five-star hotels, built inside ancient castles or original monasteries and allowing you to stay within the realms of history. Of course, the castles are always iconically situated, dominating the center of a walled city and commanding stunning views across the surrounding valleys. While other visitors photograph and admire the six centuries old walls, you enter through the gates to be treated like royalty.

After Oropesa, you spend days two and three in Jarandilla de la Vera and Plasencia, both sublime old towns graced by Gothic cathedrals and numerous palaces. All transfers are by luxury vehicles and the days are free to absorb the atmosphere of a lost corner of Europe. Trujillo welcomes you from afar on day four, the medieval hilltop town catapulting you directly into the 16th century. This was the home of Francisco Pizarro, arguably Spain's most famous conquistador, and his town is an ode to the wealth he plundered. Spend the day being guided through the monuments before day five is left free for you to explore at leisure.

Rewind the clock further by arriving in Caceres, a mesmerizing walled city that had its aristocratic heyday in the 15th century. Brimming with relics from across the ages, Caceres feels like a living encyclopedia of medieval Western empires, the streets filled with Moorish, Catholic, and Spanish monarch's architecture. Next, you travel to 25 BC and Merida, perhaps the world's finest preserved Roman city outside of Rome itself. The two days allow you to absorb the monuments at leisure, including an illustrious amphitheater and fascinating Roman art museum. Like Caceres and Trujillo, one day includes a guided tour that breathes narratives into the old stone. The other is at your leisure.

Finish the journey by crossing the old drawbridge and submerging yourself in Toledo, arguably Europe's finest medieval city. You're back in the Castle of Oropesa, with two full days to discover the jewels and charms of a destination that spans 2000 years. Included in the guided tour is a look at the battles of El Cid and a visit to master painter El Greco's former residence. Like always, the free time allows you to really experience a timeless destination. Relax in cafes down cobbled streets, dine al fresco on the famous Plaza Mayor, and spend tranquil hours lost in the enchantment. Throughout the itinerary, little touches complete Extremadura's story, including wine tasting, tapas menus, and gala dinners in the Conquistadors' castles. 

Starting Price

$3,739 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

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