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Castilla La Mancha - The Path of Don Quixote

Follow in the footsteps of Don Quixote of La Mancha - quite arguably one of the greatest novels in the history of literature. On this journey, we embark on an incredible collection of medieval towns and villages with some of Spain's most incredible architecture. 


Experience Medieval villages and towns of Castilla La Mancha

Savour exquisite wine and gastronomy

Experience the charm and allure of the countryside

Stay in charming and intimate boutique hotels



We set off from Valencia as we enter into the Castilla La Mancha region at the heart of Spain. We begin with the spectacular and jaw-dropping village of Alcala del Jucar in the province of Albacete, set on top of a rocky outcrop overlooking a bend in the Jucar river. Considered to be one of Spain's most beautiful villages, explore the dramatic white houses that cascades down mountain cliffs dominated by its Arab fortress first built by the Moors. From here, a short drive takes us to the Bodega Iniesta wine estate, owned by none other than World Cup 2010 winner and former FC Barcelona football player, Andres Iniesta. Enjoy a tour of the sprawling estate that spreads over 400 hectares where we get to meet the ace midfielder's father who runs the winery, learn about the Iniesta brand's passion for wine-making and tasting. 

Thereafter, we continue our journey through some of Castilla La Mancha's captivating landscapes dotted with vineyards of the Valdepenas wine-making region. Make a stop at the ancient ruins of the stunning Motilla del Azuer fortress, that dates more than 3,200 years. Constructed during the Bronze Age, it contains the oldest well in the Iberian Peninsula where we learn about its functional purpose and importance to its occupants and settlements. Finally, we will arrive in the traditional town of Almagro where we spend the night in the historic Parador de Almagro


No, you will not get to meet Andres Iniesta. He's currently plying his football in Japan!

Overnight: Parador de Almagro, Almagro

Meals: NIL

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An inspiring day begins with an orientation of Almagro in the heart of the Ciudad Real province, with its vibrant urban design renowned for its 17th Century Corral de Comedias Theater which plays host to the annual International Classical Theatre Festival, a theater predating Shakespeare and the dramatists of the Siglo de Oro. Enjoy a walk of the Plaza Mayor with its fine arcaded and colonnaded buildings, each with green framed windows - legacy of the Fugger family's influence. A walk round the town reveals many architectural treasures such as the Maestri palace, and the place of the Counts of Valparaiso among many fine buildings.  

We then leave Almagro journeying north on the "Path of Don Quixote" where we arrive in the town of Campo de Criptana where according to Cervantist scholars, it was here that Don Quixote's most popular and well-known adventure took place: his battle against the giants that turned out to be windmills. The most characteristic feature of Campo de Criptana are the windmills and the Albaicín Criptano, with its narrow streets, steep slopes and whitewashed one-story houses with indigo skirting boards typical of La Mancha. Initially built to grind grain, the mills were modeled on the Dutch windmills of the 16th and 17th centuries, with a cylindrical tower and conical deck where the shaft and its four rectangular blades are housed. From here, we continue our drive north to arrive into the historic city of Toledo, dating back to the Roman Period circa 192 BC. Check in at the beautiful environments of the El Cigarral de las Mercedes

Overnight: El Cigarral de las Mercedes, Toledo

Meals: Breakfast 

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Dedicate the day to uncover the UNESCO World Heritage-listed city of Toledo, considered as one of Spain's most impressive ancient city that has witnessed occupation by the Romans, Visigoths and the Moors before its reconquest in 1085 AD. The former capital of Spain thrills with its incredible architectural feats, arts that includes many works from El Greco. Enjoy an informative tour of Toledo, nicknamed "City of Three Cultures" where Jews, Christians and Muslims co-existed for hundreds of years as we take a step back in time wandering through Toledo's maze-like medieval streets and by visiting its famous cathedrals, palaces, synagogue and art museums. 

Overnight: El Cigarral de las Mercedes, Toledo

Meals: Breakfast 



We leave Toledo today for the UNESCO World Heritage listed town of Aranjuez visiting the Royal Palace - summer residence of the royal family in the 6th Century, created during the reign of Ferdinand VI. The town's Baroque and Rococo palaces, geometrically laid-out avenues, central squares, and gardens along the Tagus River embody the orderly ideas of the Enlightenment. Explore the palace that was originally built for Philip II in 1560 but was rebuilt in the 1660s. The impressive facade is mainly Renaissance in design with Baroque influences. 

From here, we drive eastwards to arrive at the spectacular UNESCO-listed medieval fortified city of Cuenca (not to be confused with Ecuador's in South America), perched and built majestically on a look-out point between the gorges of the Huécar and Júcar rivers. Start exploring the city's medieval cobblestone lanes, town square and picturesque alleys that evokes a timeless atmosphere and the Casas Colgadas "Hanging Houses", clinging precariously to the cliff side provides the most emblematic sight of Cuenca. Other monumental sights we will uncover include the 12th Century Cuenca Cathedral with its stunning mix of Norman and Gothic architecture and in a commanding position opposite the Hanging Houses, lies the Parador de Cuenca, former convent of San Pablo built in the 16th Century that has been redesigned into a luxury hotel set on top a rocky promontory in a dramatic setting.


Finally, we head on into the province of Guadalajara (not to be confused with Mexico) to arrive into the nostalgic town of Siguenza where we spend the next 2 nights at the Molino de Alcuneza, a Relais & Chateaux property.  

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Overnight: Molino de Alcuneza, Siguenza

Meals: Breakfast


Enjoy a relaxing day as we begin to explore Siguenza with its strong cultural identity. Dominating the town is the Castillo de Siguenza, a stunning fortified 12th Century castle built on the site of a Moorish Alcazaba. Wander the old streets lined with exceptional historic buildings with the Plaza Mayor at the center of attention with its beautiful Renaissance period houses. 

The annual Festival de la Lavanda:

Depending on your season of travel and dates, an opportunity to participate in the annual Festival de la Lavanda where the fields of Brihuega are blanketed in endless stretches of lavenders, teasing all the senses where with our VIP arrangements, enjoy a front row spectacle of incredible music performed by renowned Spanish artistes before settling down for an outdoor Michelin dining experience curated by 2 Michelin star Chef Dani Garcia.

Overnight: Molino de Alcuneza, Siguenza

Meals: Breakfast

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Leaving Siguenza today, our pleasant drive sees us arriving into the UNESCO-listed town of Alcala de Henares - birthplace of Miguel de Cervantes, author of Don Quixote, as well as the Emperor Ferdinand I. Take a walking tour through the historic heart of the town that has all the influence of Cervantes' greatest works starting from the Calle Mayor - bustling with restaurants, cafés, pastry shops, and little boutiques. Enjoy a visit to the Cervantes Museum, a reproduction of the 16th Century house where Cervantes was born that furnished in the style of the period and contains memoirs of Cervantes. 

Thereafter, we transfer to Madrid Barajas Adolfo Suarez Intl Airport for your flight home or continue your exploration of Madrid and surrounds that wows with a number of historic sites that include the likes of UNESCO World Heritage-listed ancient cities of Avila, Segovia, San Lorenzo del Escorial and beyond. 

Meals: Breakfast 

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Formerly the Convent of San Francisco of Almagro built by the Davila de la Cueva family, the Parador de Almagro is now a reconverted hotel with an elegant, serene atmosphere and this is reflected in the bedrooms and public areas. The bedrooms, originally the monastic cells, are a haven of peace and tranquility. 

Parador de Almagro, Almagro

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El Cigarral de las Mercedes, Toledo


A dreamy wedding event venue turned into a boutique luxury hotel that offers an  impressive panoramic view of the city of Toledo and combines its tradition and origins with a renewed classic style and modern decoration taken care of down to the last detail.

A Relais & Chateaux property, the Molino de Alcuneza is a few minutes from the historic medieval town of Siguenza This characteristic building dating from the fourteenth century offers comfortable and bright rooms and suites with stunning views of the valley of the Alto Henares while savoring to the excellent culinary fares of Michelin star Chef Samual Moreno. 

Molino de Alcuneza, Siguenza

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