See a different side of Spain on a nine-day road trip that takes you from Madrid to the arid plateau region of La Mancha. This land of Don Quixote is a major wine-producing region, which you'll discover on a tasting excursion. You'll also visit historic medieval towns like Villanueva de los Infantes and the romantic waterfalls of Ruidera Lakes.


  • See the most famous sights of Madrid on a guided walk
  • Visit Toledo, a historic city that was once the capital of Old Spain
  • Embark on a road trip through La Mancha
  • Stop at unspoiled national parks like Daimiel and Ruidera Lakes
  • Taste wine in the Valdepeñas region

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Madrid, Explore the City Madrid
Day 2 Pick up Rental Car & Drive to Toledo Toledo
Day 3 Drive to Daimiel, Explore La Mancha Daimiel
Day 4 Drive to Almagro, Visit the National Park Almagro
Day 5 Explore Almagro, Optional Day Trip to Campo de Calatrava Almagro
Day 6 Drive to Villanueva, Wine Excursion Villanueva de los Infantes
Day 7 Enjoy Villanueva de los Infantes Villanueva de los Infantes
Day 8 Drive to Alcázar de San Juan via Ruidera Lakes Alcázar de San Juan
Day 9 Return to Madrid & Depart  

Detailed Itinerary

Day 1: Arrive in Madrid, Explore the City

Madrid at night
Madrid at night

Welcome to Spain! Upon arrival at the nation's capital, you'll enjoy a private transfer to your hotel in the city center. Take some time to settle in before heading out to explore highlights like the Puerta del Sol, one of the city's most historic and expansive plazas. There's also Madrid's famous Fountain of Cibeles, with its 18th-century sculpture depicting Cybele, the Greek goddess of fertility, riding in a chariot pulled by lions.

Another option is to take in a show. Gran Vía is Madrid's answer to Broadway; on it, you'll find plenty of theaters showcasing plays and musical productions. Needless to say, the options for culture in this city are vast, and you could also visit museums, art galleries, and live music venues if the mood strikes.

When night falls, be sure to indulge in Madrid's world-class culinary scene. If you want to dine amid history, head to Botín. No less than Ernest Hemingway described it in his seminal novel "The Sun Also Rises" as the best restaurant on Earth. 

Day 2: Pick up Rental Car & Drive to Toledo

Toledo and its iconic Alcázar
Toledo and its iconic Alcázar

In the morning, you'll pick up your rental car and embark on a day trip to Toledo, located about an hour south of Madrid. You'll meet a local guide for a walk through this historic city, which enjoys a dramatic location atop a gorge overlooking the Río Tajo.

Back in the 16th century, Toledo was the capital of Old Spain. During this time, Toledo was known as the "City of the Three Cultures," a place where—legend has it—Christian, Muslim, and Jewish communities peacefully coexisted. You can see remnants of this in the old Arab, Muslim, and Christian monuments that still stand. These include the 15th-century Monastery of San Juan de los Reyes, the former Roman palace Alcázar de Toledo, and the Moorish Synagogue of Santa María la Blanca, which dates to the 12th century.

The walk includes stops at these historic landmarks as well as others, including the grand 13th-century Toledo Cathedral and the 12th-century Church of Santo Tomé. Throughout it all, you'll stroll the ancient streets of an incredible city that could aptly be described as an open-air museum. After all, Toledo does enjoy UNESCO World Heritage status. 

Day 3: Drive to Daimiel, Explore La Mancha

The famous windmills of La Mancha
The famous windmills of La Mancha

After breakfast, you'll begin your road trip into La Mancha. From Madrid, take the road toward the town of Consuegra on a route that passes through the arid plateaus of central Spain. This was the home region of the protagonist in Spain's most celebrated novel, "Don Quixote." He may have been a fictional character, but the windmills featured in that everlasting work by Cervantes are very real staples of La Mancha, and you'll pass by them on the drive.

You'll also enjoy a guided excursion of the area led by an expert. You'll visit the windmills and Castillo de la Muela, a well-preserved castle that dates to the 10th century. Throughout the outing, your guide will reveal insight into these landmarks to help you understand their history. An optional stop is the Saffron Museum, which features exhibits about Spanish saffron's history, cultivation, and qualities, which is said to be the best in the world. 

You'll likely work up an appetite after all that sightseeing. Around lunchtime, you can stop at a local restaurant for a traditional La Mancha meal. Afterward, continue on to Las Tablas de Daimiel, a national park protecting the area's largest wetland ecosystem. You'll stay overnight here in a hotel.

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Day 4: Drive to Almagro, Visit the National Park

Take a pleasant stroll through Tablas de Daimiel National Park
Take a pleasant stroll through Tablas de Daimiel National Park

After an early breakfast at the hotel, you'll drive to the Las Tablas de Daimiel National Park and meet your private guide. This is Spain's smallest natural park, but you wouldn't know it by the abundant flora and fauna, including migratory waterbirds, like herons and egrets, who flock to these expansive wetlands during winter. Your guide will lead you along wooden pathways to the best vantage points for viewing nesting flocks in the last floodplain wetland of the central Iberian peninsula. 

After the excursion, you'll hop back in the car and continue to Almagro, where you'll check into your hotel. This town of fewer than 10,000 people may be small in scale, but it abounds with rich history and beautiful landmarks. But the city is most famous for its 16th-century open air-theater, the Corral de Comedias. You can visit the Corral during the day tomorrow or check the calendar and see if there's an evening performance to enjoy tonight. 

Day 5: Explore Almagro, Optional Trip to Campo de Calatrava

The Plaza Mayor, Almagro
The Plaza Mayor, Almagro

In the morning, you'll meet up with an expert guide and embark on a city walk through Almagro. Its well-preserved 15th-century architecture is a throwback to when Almagro was defined by its aristocratic culture, which you can see in the stately manor homes and grand Plaza Mayor, lined with colonnaded buildings. If you didn't pop into the Corral de Comedias yesterday, don't miss it today!

In the afternoon, you have the option to visit nearby Campo de Calatrava, a comarca (a traditional region) known for volcanic hills and glassy lagoons. It was named after the military Order of Calatrava, which controlled the region in the 10th-12th centuries when La Mancha was the frontier between Christian and Muslim Spain. Here you can visit well-preserved castles like Calatrava la Nueva and interesting archaeological sites like Oreto and Zuqueca, home to the remains of a Visigoth cemetery and an ancient Muslim city.

Day 6: Drive to Villanueva, Wine Excursion

Tour the vineyards of La Mancha
Tour the vineyards of La Mancha

After breakfast, you'll continue your road trip to the well-preserved medieval town of Villanueva de los Infantes. Stop off along the way for a wine tour of Valdepeñas. Not only does this region enjoy the Designation of Origin (DO) mark of quality, but La Mancha is also the world's largest continuous wine-growing region with over 300 vineyards and 22,000 grape growers.

With your expert wine guide, you'll learn about the different grape varieties grown in the region, the care and techniques that go into harvesting grapes on a small-production vineyard, and the external factors that can influence the quality of the grapes—everything from the weather to astrology. Then visit the winery to see the enormous terracotta fermentation containers and sample wines like Grenache and Tempranillo. 

In the afternoon, you can either hang out around Valdepeñas and enjoy the town or continue to Villanueva de los Infantes. Upon arrival, you'll check into your hotel and can spend the remainder of the day relaxing.

Day 7: Enjoy Villanueva de los Infantes

Plaza Mayor, Villanueva de los Infantes
Plaza Mayor, Villanueva de los Infantes

In the morning, you'll meet a local expert guide for a walk through Villanueva de los Infantes. With its early 17th-century Plaza Mayor (central plaza) and various medieval hermitages and convents, this village is straight out of the mind of Cervantes. In fact, Villanueva de los Infantes is generally accepted to be the town referenced at the beginning of "Don Quixote" as the title character's home. 

You'll visit the major sites in town, including the Plaza Mayor and St. Andres Church, where the famed poet Francisco de Quevedo is buried. You'll also stroll cobbled streets lined with medieval manor houses with their well-preserved history. When the sun sets, head out for dinner to discover and enjoy genuine La Mancha cuisine.

Day 8: Drive to Alcázar de San Juan via Ruidera Lakes

Lagunas del Ruidera
Lagunas del Ruidera

After a leisurely breakfast in Villanueva de los Infantes, you'll drive to the town of Alcázar de San Juan. On the way, stop at another wetland region: Lagunas del Ruidera. This oasis in La Mancha is comprised of 16 glassy lakes connected by cascading waterfalls. With its many beaches and swimming areas, the environment is almost tropical yet firmly rooted in La Mancha—the lakes are even referenced in "Don Quixote." 

After spending the morning and part of the afternoon enjoying the lakes, you'll take a break for lunch. Instead of traditional Spanish cuisine, you'll dine at a restaurant that has won international awards for having the best pizza in Spain for many years running. Afterward, should you choose, you can enjoy a tasting of artisanal brandies at a nearby distillery. 

Later in the afternoon, you'll continue to Alcazar de San Juan, where you'll check into your hotel and have the evening free.

Day 9: Return to Madrid & Depart

The Campo de Criptana windmills
The Campo de Criptana windmills

In the morning, you'll drive 1.5 hours to Madrid to catch your flight home. Don't worry, though; you can enjoy one or two more activities in La Mancha before your plane leaves. You could visit the famous Campo de Criptana windmills or attend a private workshop in the town of Villafranca for a hands-on lesson in producing traditional terracotta ceramics. You can even visit a farm that produces award-winning Manchego cheese from sheep's milk, with tastings included.

Whatever you decide, eventually you'll arrive at the airport in Madrid. This concludes your grand journey through La Mancha. Adiós, and come back soon!


Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 9 days
Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 9 days