The Don Quixote Tour of Spain: In the Footsteps of a 400 Year Old Masterpiece

A 11 day trip to Spain 
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Don Quixote is the epitome of ancient Spain, a surrealist adventure blessed with unrivaled poetry and fantasy. Celebrating the 400 year anniversary of Cervantes’ masterpiece, this handcrafted itinerary recaptures the Spain of Don Quixote, taking a seductive route bathed in history and legend. Windmills, walled towns, wine estates, paradors; the fictional blurs with the exquisite as you recreate a knightly story and one of the greatest works of Western literature.

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General Information

Detailed Itinerary

Places Visited 

Toledo, La Mancha, Castle of Oropesa, Oropesa, Orgaz, Mora, Tembleque, El Romeral, Villacanas, Madridejos, Consuegra, Quintanar de la Orden, El Toboso, Almagro, Manzanares, Valdepanas, Santa Cruz de Mudela, Madrid, Palace of Aranjeuz, Royal Palace, Cava Baja Street

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Oropesa – Mystical Welcome into one of Spain's Finest Ancient Towns

The Castle of Oropesa stands sentinel above Toledo, the turrets and cupolas dominating a medieval town of indulgence. Cross the 11th century stone bridge and you're lost within the fiction of yesteryear, the cobbled streets winding past restaurant terraces and statuesque heroes. Built in the early 15th century, the Castle of Oropesa is your first parador, your first night in historic luxury accommodation. You're met in Madrid by your driver guide and head directly to this fairytale fortress. The afternoon is at your leisure before the evening is filled with a mystical immersion into the past. A gala dinner is served in the castle's grand dining hall, with live entertainment and a multitude of different dishes served with wine.

What's Included: accommodation, luxury transfers, dinner

Day 2: Oropesa – Lost in Medieval Fantasy and Fiction

Church bells chime as the cafes spill morning scents onto the streets of Oropesa. You're in La Mancha, land of reviving chivalry and the imagined exploits of knights. As you explore the medieval utopia it's easy to see where Cervantes’ idealistic imagination had its roots. Dip into the Jewish quarter and its taverns of enchantment, then discover the cathedral and its crypt of conquistadores. Two quaint plazas make ideal spots for a leisurely lunch, cute lids of tapas served with every drink order. Inside the castle there are tales of El Cid and his meandering conquering, further influence on the greatest Spanish book of all time. Today is at your leisure and enables you to fully relax and settle into the rhythm of historic Spain. Take your time. Get lost. And absorb the culture and tradition that permeates all across La Mancha.

What's Included: accommodation, breakfast

Day 3: Mora – The Cute Towns of Cervantes’ Masterpiece

La Mancha's noble towns are coated in poetry: Cervantes’ elegant sentences of fantasy emanating from the stone courtyards that gaze across the region's plains. Today starts in Orgaz, where a medieval castle and various sublime casas patrol streets of tempting tapas bars. Enter beneath the archway of San Jose and you're guided into churches and noble family homes, the settings from Don Quixote blurring away from the fictional. Enjoy lunch here, on a terrace that overlooks the buildings of history. In the afternoon you visit Arisgotas and its Visigoth Museum, before continuing to Mora, renowned for its fabulous olive oil. Finally, you're guided through the Oil Mill Museum, before the evening is left free for you to indulge in the charms of a town lost in time.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch

Day 4: Consuengra – A Journey Through the Windmills and Ancient Villages of La Mancha

There's a single iconic La Mancha sight that excites most imaginations; the wild giants with huge arms that Sancho Panza calmly clarified were windmills. They stand proudly on the green plains, occasionally turning with slow artistic grace. When Panza informed his master that these weren't giants but windmills, Quixote's reply was to say, “obviously, you don't know much about adventures.” And today's journey is an adventure, connecting La Mancha's famous windmills with its deserted villages. Explore the castle of Piedras Negras, gaze upon the windmills of Tembleque, then head inside the four stunning windmills of tiny El Romeral. Lunch comes with a view, the local Manchego cheese combined with some excellent local red wine.

Villacanas is nearby, a town that descends into underground dwellings and caverns illuminated by oil lanterns. It's here you visit the Tio Sandalia House and the Silo Ethnographic Museum, both seductive looks at the history of the region. On the Consuegra crest of La Mancha is where 12 famous 16th century windmills form the most famous image from the book. Tonight's accommodation is in a converted farmhouse on the edge of town and the evening is free to explore streets of old churches and pottery workshops.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch

Day 5: El Toboso – Wine Tasting at the Home of Don Quixote's Greatest Love

Fantastic samples of wine provide a base for discovering the kingdom of Dulcinea del Toboso, Don Quixote's great love. At the Condesa de Leganza winery, a variety of La Mancha wines make for an easy introduction in this famed vineyard area. Whitewashed terraces line El Toboso's near deserted streets, each footstep taking you on a curved journey through a town that evokes 16th century beauty. Quixote wooed Dulcinea with his shows of chivalry and knightly deeds, and the Venta de Don Quijote winery is where Cervantes’ character received his knighthood. Enjoy a lavish lunch banquet, complemented by eight wines from a vast vintage cellar. And while the book is imagined through the hero's eyes, one line sums up the feeling of today: “The truth may be stretched thin, but it never breaks...”

What's Included: accommodation, luxury transfers, guide, breakfast, lunch, wine tasting at two wineries

Day 6: Almagro – A Fabulous Parador in a Delightful Town

Almagro stands resplendent above the La Mancha plains, an almost mythical expanse of white rising like a cloud above the region's flatlands. Like always, your transfer here is by luxury saloon and the day runs at a very leisurely pace. There's no need for early starts in this historic land of siestas and fiestas. Start the Almagro guided journey in the open-air Corral de Comedias, a Romanesque theater of allure. Palaces and aristocratic casas line the streets, each of them painted white, each a little piece in the coherent architectural jigsaw of Almagro. Lounge on the Plaza Mayor, lunch being served in one of Spain's cutest squares. After checking into your historic parador, a charming old building glamorized with modern luxury touches, the rest of the day is at your leisure.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch

Day 7: Manzanares – Visiting Cervantes’ Prison and Relaxing on La Mancha Plains

Don Quixote's freedom was the imagination of a man incarcerated. It was at the Argamasilla de Alba prison that Cervantes was jailed and wrote his masterpiece. A humble cave is hidden beneath the unassuming facade of an Argamasilla de Alba townhouse. Head into the gloom and stand in the makeshift prison room, little natural light available to write with a quill. Your literary guide picks up the narrative, describing Cervantes’ noble past and his arguments with the local villagers.

As you head into the mountains the natural splendor of La Mancha begins to impress. Spend the afternoon gently exploring the lagoons of Ruidera Lakes Natural Park, an idyllic spot to enjoy a picnic of Iberico jamon and cheese. Tucked on the outskirts of the park, overlooking the Tablas de Daimiel National Park, your Monzanares parador is one of Spain's most sublime. Birdsong flutters from the overgrown gardens while a river of blue passes by the old fortress windows. An excellent tapas restaurant has been chosen for tonight, serving a fine selection of classic dishes to the accompaniment of wine from nearby vineyards.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch, dinner

Day 8: Valdepanas – A Day of Wine and Castles in the Mountains

As you meander further into the mountains you can picture the scene: Quixote riding his trusty Rocinante and imagining tales of deception. While the original book was published in 1605, the sequel arrived ten years later and fully bound Quixote to the acts of chivalry that would lead to his madness. As you explore seemingly endless rows of Tempranillo and Garnacha grapes, vineyard owners who love the stories of legend faithfully narrate the stories. You visit three wineries today, including the Valdepanas Wine Museum, and the opulent Vina Abali winery. Meet the growers at each of them and join them in reminiscing over samples of their finest vintage. As the senses are aroused you gently indulge in a region that's rarely visited yet is hypnotically traditional.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch, wine tasting at three wineries

Day 9: Tomelloso – The Town of Cervantes’ Imagination

“Somewhere in La Mancha, in a place whose name I do not care to remember...” and so start many of Cervantes’ descriptions. A huge collection of La Mancha villages claim to be the author's inspiration, but historians are relatively consistent in naming Tomelloso as the village Quixote's adventures start from. It's a town that defies the imagination, Renaissance beauty standing above statues of horse-riding heroes and terraces smelling of red wine and coffee. While many nearby villages are virtually abandoned, Tomelloso lives on with a social atmosphere and lazy hours spent at the Plaza Mayor. The town’s revelations of Spanish tradition continue from a lunch besides the Town Hall to an evening of tapas in the historic town taverns.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch, dinner

Day 10: Madrid – Palaces and Tapas in Spain's Capital

Marble columns glisten at the Palace of Aranjeuz, their whiteness shimmering above large cultivated gardens perfect for a stroll. Halfway back to Madrid, this UNESCO World Heritage site is the monarchy's official residence. Corridors are lined with portraits made with oil swirls, while jewels glimmer beneath gilded gold ceilings. As you continue to the capital, Western Europe's largest palace is the second guided stop of the day. Stretching out above Madrid, the Royal Palace is an ode to excess and the pomp of yesteryear, each room filled with aristocratic collections of art and antiques. Your hotel is in the heart of Madrid, nestled along historic streets that are easy to explore on foot. Completing the day is a guided tapas hop along Cava Baja Street, each little bar specializing in a couple of exquisite dishes that reflect the inimitability of this tour.

What's Included: accommodation, luxury transfers, guide, breakfast, lunch, dinner

Day 11: Madrid – Departure

This morning you depart Spain, full of memories that make the pages of Don Quixote seem far more real than they initially seemed. Say goodbye to your driver guide at Madrid Airport and rise above the country, destined to return for more unique immersions in the culture and history of Spain.

What's Included: luxury transfers, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.