Oropesa, Jarandilla de la Vera, Plasencia, Trujillo, Toledo, Madrid, Caceres
Dates are flexible and customizable for private departures.
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.
Oropesa – Spectacular Welcome in One of Spain's Finest Paradors
The Castle of Oropesa towers above Toledo, dominating the landscape with its medieval dreams. It's almost like a fairytale, the fortress guiding you towards to the top of a kingdom. You are barely an hour from Madrid Airport and you've already stepped back in time. Don't just admire the castle from the outside. Head inside to the hand-painted ceramics, every corridor lined with the personal collection of the renowned Alvarez family. This is perhaps Spain's finest Parador, a sublime castle filled with Renaissance art and updated to provide 21st-century luxury. Settle in and spend the afternoon wandering the turrets and towers of the original castle. A sumptuous gala dinner is served in the Parador's immense dining hall, a banquet of local flavors served with some of the country's finest reserva wine.
Jarandilla de la Vera – Reliving Royal History
The landscape of Extremadura is filled with memories. Royal palaces sweep columns of beauty across the Gredos Mountains. Crumbling 15th-century houses stand between overgrown olive trees. Standing like sentinels on the highest hills are the castles of history, their moats now dry but their elegance living on. Today's journey takes you out of the arid central plateau and into hills of billowing oak groves and chestnut trees. Jarandilla de la Vera is tiny and seems almost deserted. Hardly anything has been built since the 16th century and gradually the town has fallen off the map. But what remains is like a piece of art, a canvas of stone streets, churches, and palaces. Tonight's Parador is a castle-cum-palace, one that's not afraid to boast of when Carlos V lived here. Explore the tranquility and absorb the antiquity; the whole afternoon is at your leisure until dinner is served in the most regal of settings.
Plasencia – Journeying Through the Ancient Homelands of Spanish Explorers
A stone bridge curves across the River Jerte, marking the entrance to the old quarter of Plasencia. Two rows of 12th-century walls surround the remains of the town, protecting the Romanesque cathedrals and their spires. It's less than an hour's drive to Plasencia, the home of King Ferdinand during the Conquistadors ventures into the Americas. Great chests of silver funded the city's growth, filling it with Gothic churches and Renaissance palaces. A local guide provides a tour of the city, starting along the walls then exploring the complex of cathedrals and churches that have survived the centuries.
Finish on the Plaza Mayor, gazing upon a series of palaces and enjoying the ambient chatter that emerges from terraces. A 14th-century spire, a balcony of red, a roof of slate; every angle offers a new touch to the skyline as you spend the rest of the day on one of Spain's most charming squares. Dinner is enjoyed at the town's most acclaimed tapas restaurant, a series of sumptuous dishes suggestive of discerning tastes. Expect some outstanding jamon and chorizo to feature highly. Retire to your Parador at leisure, tonight's bedroom tucked away in a converted Gothic monastery.
Day 4 - 5
Trujillo – Reliving the Regal Town of Conquistador Pizarro
Along with Hernan Cortes, Francisco Pizarro was Spain's most famous conquistador, an explorer who made an irrefutable stamp on the history of the Americas. His hometown still clings to the hill, seemingly unperturbed since its favorite son founded the first Spanish colony in Peru. Understandably, he's a local hero: a statue of his likeness riding a horse is featured in the grand Plaza Mayor. As Pizarro conquered, his personal wealth came back here, funding the town's majestic palaces and lavish medieval streets. After the short drive from Plasencia, you will be greeted by an expert historical guide who will tell the tales of Pizarro's influence on both sides of the Atlantic.
Nothing breaks the spell in Trujillo. Not the central square and its Renaissance terraces, nor the church of Santiago or the walls that box in the old town. Everything is as if Pizarro was still alive today, the mythical concoction of stone traversed by horse and carriage, not exhaust fumes. Two palaces add doses of grandeur, both funded by Pizarro. First Palacio de Marques de la Conquista, an imposing mass of fortressed power, then Palacio of Orellana-Pizarro, far more ornate and delicate in its revelations of the 16th century. You'll also visit Pizarro's museum, situated inside his former home. Lunch is included and will focus on the local specialty of black Iberico pig.
Towns like Trujillo have a dual beauty. There are the famous architecture and monuments, the sights that scream of history, and fill the camera with iconic photos. Then there's the old-world charm and atmosphere, something that can't be easily captured yet permeates through every moment spent. Day four is fully guided and features all the town's core attractions. Day five is at your leisure, a time for simply wandering and immersing yourself in history. Accommodation in Trujillo is at a 16th-century former convent, elegantly restored and complete with swimming pool hidden between old stone walls.
Day 6 - 7
Caceres – Immersed in the Medieval Beauty of Caceres
At first glance, the history of Caceres is difficult to unravel. Its maze of narrow alleys twists and turns ascending to palaces of peculiar heritage. Minarets and a mosque's dome peek above one wall while a cathedral's bell rings in the distance. Keep walking and whitewashed stone marks the corridors of the Jewish Quarter, then the cobbles descend to a town square that blurs its architecture across the centuries. Caceres, Spain's first UNESCO World Heritage City has its roots in the Moors and the evidence of exotic Islamic beauty still finds a space within the maze. It was conquered in the 13th century and blossomed into a haven for trade, the merchants' commission plowed into immense Catholic cathedrals that still dominate the old city. Most of the surviving buildings date to the 15th and 16th centuries, continuing the theme of medieval musing.
Arrive in Caceres and a local guide takes you on a full-day walking tour of the Old Town. Dip inside the Church of San Mateo and then stand baffled at the House of Storks, an 800-year-old tower filled with storks' nests. Step inside royal palaces and appreciate their rooms of indulgence. Enter cathedrals and churches that shimmer with silver and Gothic design, every wall swirling with the extravagance of the Conquistadors' Catholicism. Like Trujillo, the first day here is about discovering the town's history and admiring the stunning historic buildings. Your hotel is in the heart of the Old Town, a boutique five-star guesthouse with elegant views over the rooftops.
Caceres has more under its hat than the Conquistadors era. While the atmosphere continues to be one of centuries past, the town's twisting cobbles also emit the scents of gourmet brilliance. Caceres was Spain's gastronomic capital in 2015 and your itinerary includes two very different local dinners. First it's delicate and dainty tapas at the town's most renowned tapas restaurant. The dishes are small, half a dozen flavors packed into a single bite, and the dishes keep getting delivered to the table. On day eight you dine at the double Michelin Starred Atrio, every experimental dish on the tasting menu combined with something from Jose Polo's world-famous wine list.
Day 8 - 9
Merida – Stunning Remains and an Elegant Parador in the Roman City
Keep rewinding the clock, spinning through the Moorish times, and find yourself in the Western Roman Empire. Merida is another city lost in a time warp, a flute of columns immediately impressing as you arrive at the station. The journey from Caceres to Merida is by first class train and you're greeted in Merida by a local guide. Another of Spain's finest Paradors, your accommodation in Merida is in a stunning 16th-century convent. Check-in, admire the historical reverie that dances across the city, and then head off on a guided afternoon walking tour.
First, you will find the Roman Theatre, an effortless ode to early Western civilization. Perfectly preserved, it's one of the most complete examples on the planet and a fitting start to the journey into Emperor Augustus's times. Now you will come to the old amphitheater, the steep steps fulfilling all preconceptions and the stage still hosting an annual drama festival. Depending on your travel dates you may have an opportunity to watch a performance in this two millennia-old venue. Keep wandering. Next, you go through underground galleries brightened by Roman mosaics, beneath the Temple of Diana with its columns that seem to steeple above the world, and now to the Arch of Trojan, an iconic photo of the Roman Empire. Your tour culminates in the National Museum of Roman Art, each room filled with relics and reminders from the empire's cities all across Spain. Day nine is at your leisure.
Day 10 - 11
Toledo – Getting Lost in the Splendor of an Untouched Walled City
With a second first-class train journey, the sense of fairytale returns. You're back at the Castle of Oropesa, lost amongst the cupulas and towers of the ancient walled city of Toledo. While day one provided a royal introduction, these final two days offer the time to truly discover another of Europe's most exquisite towns. From the castle's terrace you see the Puerta Antigua de Bisagra, the 11th century gateway that marks the boundary between medieval utopia and the rest of the world. Explore the Jewish quarter with its shops of local delights, meander past taverns of treats, and look around for something to contradict. Like Trujillo, Toledo has laid its foundations and won't be moving forward to a more modern era.
During the tour, the history of Toledo is revealed through its monuments. In the cathedral lies the crypt of its explorers. Enter El Greco's former home and the artist's masterpieces evoke scenes from the city's history. And inside the fortresses you hear tales of El Cid's conquering and the explorers returning. It's a town you don't want to leave and you don't have to; day 11 left free for you to wander at leisure and absorb the final memoirs to castles and Conquistadors. A farewell dinner rounds off the itinerary, served at the parador as the sun gently sets across Extremadura.
Madrid – Departure
Depart Toledo this morning for the 90-minute transfer to Madrid Airport. As always, road transfers are in luxury chauffeured vehicles. Return to the modern world as you ascend above Spain, glimpses of ancient towns fading away beneath the wingtips.
- 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
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.
$2,875 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.
- 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.
Reviews of Zicasso's Referral Service
4.9 stars based on 1972 reviews
"Our travel planner did an outstanding job of communicating...
Reviewed By Mac M.
"The travel agent and his team were professional from the...
Reviewed By Nirvi B.
"The trip was well planned and taken into consideration...
Reviewed By Lili Z.
"[Our travel planner] was flexible when we needed to change...
Reviewed By Ellen Z.
"Would highly recommend!"
Reviewed By Rendi W.
"We stayed and viewed some of the most breathtaking scenes/sights/views...
Reviewed By Cynthia P.
Get Weekly Inspiration and Expert Advice on Travel
during the COVID and post-COVID era