Spain is filled with historic regions abounding with well-preserved ancient cities, like La Mancha. This dry plateau region is located south of Madrid, and you'll discover its historical and literary legacy (it's Don Quixote's home region) on a self-drive road trip. Along the way, you'll imbibe in La Mancha's wine, visit its national parks, and travel farther west to Extremadura and medieval cities like Mérida and Cáceres. 


  • See the most famous sights of Madrid on a guided walk
  • Embark on a road trip through La Mancha
  • Stop for a wine tour in La Mancha's vineyards
  • Visit national parks and go on a photo safari
  • Tour historic medieval/Moorish towns like Mérida and Cáceres

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Madrid, Evening Tapas Experience Madrid
Day 2 Private City Walk, Discover Madrid's Royal Legacy Madrid
Day 3 Pick up Rental Car, Drive to Toledo, City Walk Toledo
Day 4 Drive to Almagro via Las Tablas de Daimiel Almagro
Day 5 Explore La Mancha, Drive to Valdepeñas Valdepeñas
Day 6 Wine Excursion in La Mancha Valdepeñas
Day 7 Drive to Mérida, Guided City Walk Mérida
Day 8 Drive to Cáceres, Explore the Old Town Cáceres
Day 9 Drive to Trujillo, Guided Walk Trujillo
Day 10 Day Trip to Monfragüe National Park Trujillo
Day 11 Drive to Madrid, Free Day in the City Madrid
Day 12 Depart Madrid  

Detailed Itinerary

Day 1: Arrive in Madrid, Evening Tapas Experience

The Fountain of Cibeles, in Madrid
The Fountain of Cibeles, in Madrid

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 an 18th-century sculpture depicting Cybele, the Greek goddess of fertility, riding in a chariot pulled by lions.

In the evening, you'll dig into Madrid's culture on a two-hour walking excursion that stops at some great tapas bars. On this walk, you'll visit Barrio Las Letras, which is known as the "literary quarter." This historic neighborhood in the city center was once home to Spanish literary legends like Cervantes and Quevedo. Besides visiting some historical sites around here, you'll also stop at Calle Huertas for a bite at one of the many tapas bars that line the street.

Day 2: Private City Walk, Discover Madrid's Royal Legacy

The Royal Palace, Madrid
The Royal Palace, Madrid

Enjoy a half-day outing in Madrid led by an expert local guide. Madrid has a long history, and today the city adorns itself with that history in its architecture, public spaces, and culture. One area you'll visit is the Madrid de los Austrias. It was built in the 16th century during the reign of the Hapsburg Dynasty's first ruler, Charles I, and is home to one of the grandest plazas in Spain, the Plaza Mayor, which was once the heart of Old Madrid.

You'll also visit the Royal Palace, the official home of the Spanish monarchs until 1931. You'll visit both the grounds and interior of this 3,418-room monument, entering the parade ground, the chambers of Charles III, several salons, the Royal Chapel, and the Hall of the Crown, which displays Charles I's crown, scepter, and throne.

Later you could visit El Retiro Park, the green lung of Madrid, abounding with sculptures, fountains, and an artificial lake perfect for taking a boat trip. There are also must-visit gardens here, including the Jardín de Vivaces ("Garden of Vivacious Plants"), Jardines de Cecilio Rodríguez (inspired by the Andalusia region), and a garden home to over 4,000 roses. The best time to see these blooms is from May through June. 

Day 3: Pick up Rental Car, Drive to Toledo, City Walk

Toledo and its iconic Alcázar
Toledo and its iconic Alcázar

In the morning, you'll pick up your rental car and embark on your grand road trip through Spain. The first stop is the city of Toledo, located about an hour south of Madrid. After checking into your hotel, you'll meet a local guide for a walk of this historic city, which enjoys a dramatic location atop a gorge overlooking the Río Tajo.

In the 16th century, Toledo was the capital of Spain. Back then, it 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 tour 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 tour 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 4: Drive to Almagro via Las Tablas de Daimiel

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 leave Toledo on a 1.5-hour drive south to the town of Almagro. You'll make a stop in the arid plateau region of La Mancha. This was the home of the protagonist of 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.

Your stopover has nothing to do with literature, however. Despite being an arid region, La Mancha is home to Tablas de Daimiel National Park, one of Spain's most important wetland ecosystems home to various migratory waterbirds, like herons and egrets. On a brisk walk around the park, your guide will lead you along wooden pathways to the best vantage points for viewing nesting flocks. Savor the experience because Tablas de Daimiel is the last floodplain wetland in the central Iberian peninsula.

After the tour, hop back in the car and continue to Almagro, a town that abounds with rich history and beautiful landmarks. Its well-preserved 15th-century architecture is a throwback to its aristocratic culture, which you can see in the stately manor homes, the grand Plaza Mayor, and colonnaded buildings. But the city is most famous for its 16th-century open air-theater, the Corral de Comedias. You can tour the Corral during the day, and some nights they feature performances from Spain's golden age of theater of the 16th and 17th centuries. It also hosts a theater festival in July.

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Day 5: Explore La Mancha, Drive to Valdepeñas

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

You'll hop back in the car and day trip around La Mancha in the morning. You'll have the freedom to design an itinerary according to your interests. You can enjoy a Manchego cheese workshop, a popular product around the world that many don't know is from La Mancha. Made from the Manchego sheep's milk, it has a buttery texture and comes cured or semi-cured. You'll visit a family-run farm, tour the grounds, and enjoy a hands-on lesson on how to make your own Manchego cheese.

In the afternoon, venture to the beautiful Campo de Calatrava, a comarca (traditional region) of La Mancha known for volcanic hills and glassy lagoons. This area was named after the military Order of Calatrava, which controlled the region when La Mancha was the frontier between Christian and Muslim Spain. Here you can visit castles like Calatrava la Nueva and archaeological sites like Oreto and Zuqueca, home to the remains of a Visigoth necropolis and an ancient Muslim city.

After exploring the region, you'll continue to your hotel in the rural wine-producing area of Valdepeñas in southern La Mancha. After checking in, you can spend the remainder of the day relaxing.

Day 6: Wine Excursion in La Mancha

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

Today you'll explore Valdepeñas. Not only does this region enjoy the Designation of Origin (DO) mark of quality, but La Mancha is the world's largest continuous wine-growing region with over 300 vineyards and 22,000 grape growers. Discover different grape varieties and see the care and techniques that go into harvesting grapes on a small-production vineyard. You'll learn about the external factors that can influence the quality of the grapes—everything from the weather to astrology.

After touring the vineyards, you'll visit the actual winery and see firsthand the enormous terracotta fermentation containers where the grapes become wine. Each one holds an impressive 1,585 gallons (6,000 liters). After the tour, you'll be able to sample wines like Grenache and Tempranillo.

Now it's time to eat. You can choose where to enjoy a traditional La Mancha lunch, but we suggest Villanueva de los Infantes. With its early 17th-century Plaza Mayor (central plaza) and various medieval hermitages and convents, this throwback village is straight out of the mind of Cervantes. After eating, you'll return to your hotel in wine country and have the remainder of the afternoon free to enjoy the hotel or town.

Day 7: Drive to Mérida, Guided City Walk

The Roman Theater, Mérida
The Roman Theater, Mérida

This morning you'll hit the open road again, driving about 3.5 hours west from La Mancha to Mérida. This city is the capital of Extremadura and has a historical legacy dating back to Roman times. After checking into your hotel, you'll meet a local expert guide who will lead you on a walk through the city. On this stroll, you'll visit Mérida's historic center, which features more extensive Roman ruins than anywhere else in Spain. It's because of these archaeological sites that Mérida was declared World Heritage Site by UNESCO in 1986.

Mérida was founded as a Roman colony in the year 25 CE by Emperor Octavio Augustus. As the capital of the Roman province of Lusitania, it featured all the architectural hallmarks of a great city. Your guide will lead you to many of them, including the open-air Roman Theatre. Other impressive sites include the Puente Romano (stone bridge over the Guadiana River), the Circo Romano (ancient hippodrome), and the Casa del Mitreo, the remains of a Roman house with well-preserved frescoes. 

Day 8: Drive to Cáceres, Explore the Old Town

The Plaza Mayor, Cáceres
The Plaza Mayor, Cáceres

Today you'll drive about an hour north from Mérida to Cáceres. Like Mérida, this is another city with well-preserved Roman roots. It was founded by the Romans in 25 BCE and, after the end of the empire, was controlled by the Visigoths before the Moors conquered it in the eighth century. During the Middle Ages, it changed hands between the Moors and Christians for hundreds of years, as evidenced by architecture that ranges from Roman, Moorish, Northern Gothic, and Italian Renaissance.

After checking into your hotel, you'll meet an expert guide for a city walk. Cáceres has a rich legacy of conquest and reconquest between the Moors and the Christians. You'll see evidence of this in the architecture in the Ciudad Vieja (old town), encircled by walls and home to over 30 different defensive towers. You'll visit the Torre Bujaco, an Arab tower claimed by Ferdinand II of León in 1170 but retaken by the Moors in 1173. There are great views of the city skyline from the top.

Throughout the rest of the tour, you'll stroll the cobbled streets of the Ciudad Vieja and visit historic medieval palaces and fortified houses. All of this architecture reflects a city ruled by rival factions from the 14th through the 16th centuries. You'll also stop by the Plaza Mayor, one of Spain's most beautiful central plazas.

Day 9: Drive to Trujillo, Guided Walk

The Plaza Mayor, Trujillo
The Plaza Mayor, Trujillo

In the morning, you'll drive about a half-hour east to the historic town of Trujillo. After checking into your hotel, you'll meet an expert guide for a city stroll. This town dates back to Roman times, and you'll learn all about Trujillo's rich historical legacy (the conquistador Francisco Pizarro was born here). Your guide will point out the mix of Gothic, Moorish, Jewish, and Christian influences in the medieval buildings that stand to this day.

You'll visit the major sites in town, including the Plaza Mayor. This central plaza is a throwback to medieval times, and surrounding it are buildings and churches dating to the 15th and 16th centuries. In the center of the plaza, you'll find an equestrian statue of Francisco Pizarro.

Up from the plaza is the Iglesia de Santa María la Mayor, the most important church in town. Dating to the 13th century, this Gothic church features two towers, from the top of which you'll enjoy great town and countryside views. Inside, above the altar, are impressive 15th-century paintings in the Hispano-Flemish style. Naturally, the tour also includes a visit to Trujillo Castle, the 9th-century fortress that's perched on a hill overlooking the town. 

Day 10: Day Trip to Monfragüe National Park

Monfragüe National Park
Monfragüe National Park

Within the Extremadura region of Spain lies Monfragüe, a national park in the valley of the Tagus River. Besides its natural beauty, Monfragüe is known for its exotic birdlife and abundance of wild animals. In the morning, you'll transfer to the park, where you'll meet an expert naturalist who will be your guide/driver for the day.

With binoculars in hand, you'll travel through the park, stopping along the way as your guide points out fauna like black vultures, Spanish imperial eagles, various deer, river otters, foxes, and much more. The tour of the park also includes stops at famous landmarks like Salto del Gitano, a prime viewpoint overlooking the valley, and Puente del Cardenal, a stone bridge running over the Tagus River. As a bonus, you'll take a break at lunchtime for a picnic amid Monfragüe's unspoiled nature. Afterward, leave the park and transfer back to your hotel.

Day 11: Drive to Madrid, Free Day in the City

Perhaps head to Gran Vía to do some shopping
Perhaps head to Gran Vía to do some shopping

After breakfast, you'll hit the road again for the 2.5-hour drive back to Madrid. Upon arrival, you'll check into your hotel and return your rental car. You'll then have the remainder of the day free to enjoy however you see fit.

You might want to take this time to do more sightseeing and visit any locales you might have missed your first time in the city. You could also head to the shopping district along Gran Vía and pick up souvenirs and gifts to take back home. In the evening, if you'd like to dine amid history, try dinner at Botín. This Madrid staple has the distinction of being the oldest restaurant in the world.

Day 12: Depart Madrid

Goodbye, Spain
Goodbye, Spain

It's time to say farewell. After a leisurely breakfast, a car will pick you up and transfer you to the airport, where you'll catch your flight home. This concludes your great Spanish adventure. Adiós!

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Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 12 days
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