Get ready to travel the route of Don Quixote on a road trip through Spain. It begins with a city tour of Madrid before you hit the road, driving amid the arid plateaus and windmills of La Mancha and into the Extramadura region of western Spain. Here you'll tour historic towns like Cáceres and Trujillo while sampling delicious local cuisine and visiting unspoiled national parks.


  • See the most famous sights of Madrid on a guided tour
  • Embark on a road trip through La Mancha
  • Visit national parks and go on a photo safari
  • Tour historic medieval/Moorish towns like Mérida and Cáceres
  • See a live flamenco performance in Madrid

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Madrid - Evening Tapas Tour Madrid
Day 2 Private City Tour - Discover Madrid's Royal Legacy Madrid
Day 3 Pick up Rental Car - Drive to Toledo - City Tour Toledo
Day 4 Drive From Toledo to Almagro - Stop at Las Tablas de Daimiel Almagro
Day 5 Explore La Mancha - Drive to Valdepeñas Valdepeñas area
Day 6 Wine Tour of La Mancha Valdepeñas area
Day 7 Drive From La Mancha to Córdoba - Guided City Tour Córdoba
Day 8 Drive From Cordoba to Mérida - Lunch in Zafra Mérida
Day 9 Guided Tour of Mérida Mérida
Day 10 Drive from Mérida to Cáceres Cáceres
Day 11 Cáceres - Tour Old Town Cáceres
Day 12 Drive to Trujillo - Guided Tour Trujillo
Day 13 Day Trip to Monfragüe National Park Trujillo
Day 14 Drive from Trujillo to Madrid - Free Day Madrid
Day 15 Madrid City Tour - Ham Carving & Flamenco Show Madrid
Day 16 Departure from Madrid  

Detailed Itinerary

Day 1: Arrival in Madrid - Evening Tapas Tour

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. You'll definitely want to see some of the highlights like the Puerta del Sol, one of the most historic and expansive plazas in the city. There's also Madrid's famous Fountain of Cibeles. Located in the city center it features a sculpture completed in 1782 and depicting Cybele, the Greek goddess of fertility, riding in a chariot pulled by lions.

In the evening, you'll really dig into Madrid's culture on a food tour. A local expert guide will lead you on a two-hour walking excursion that stops at some great tapas bars. On this tour, 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 lit legends like Cervantes and Quevedo. Besides visiting some historic sights around here, you'll also stop on Calle Huertas for a bite at one of the many tapas bars that line the street.

Day 2: Private City Tour - Discover Madrid's Royal Legacy

The Royal Palace, Madrid
The Royal Palace, Madrid

Enjoy a half-day tour of Madrid led an expert local guide today. Madrid has a long history, and today the city adorns itself with that history in its architecture, public spaces, and culture. An organized tour is ideal, and your guide will reveal insight into how different time periods influenced Madrid's neighborhoods and buildings, as well as point out the most interesting sights.

One area you'll visit that's awash in splendor 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. Located in the city center, it's home to one of the grandest plazas in Spain, the Plaza Mayor, which was once the heart of Old Madrid.

Also here is the Royal Palace, which was the official home of the Spanish monarchs until 1931. You'll tour both the grounds and interior of this 3,418-room monument to opulence, entering the parade ground, the bedchambers 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. This 308-acre expanse of verdure is the green lung of Madrid, abounding with sculptures, fountains, and a man-made 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 from May through June. 

Day 3: Pick up Rental Car - Drive to Toledo - City Tour

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 on the map is the city of Toledo, located about an hour south of Madrid. Upon arrival, you'll check-in to your hotel, which features a breathtaking view of Toledo's city center. In the afternoon, you'll meet a local guide for a walking tour 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 From Toledo to Almagro - Stop at 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 be making a pit stop on this journey, as the route passes through the arid plateau region of La Mancha. This was the home of the Ingenious Gentleman 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. You'll drive to the entrance of the park, at which point you'll meet an expert guide who will lead you on a four-hour tour.

At 7,413 acres, this is Spain's smallest natural park, but you wouldn't know it by the abundant flora and fauna. It's home to various migratory waterbirds, like herons and egrets, who flock to these expansive wetlands during winter. 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, you'll hop back in the car and continue a short way 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. 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 that's lined with 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.

Day 5: Explore La Mancha - Drive to Valdepeñas

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

In the morning, you'll hop back in the car and day trip around La Mancha. You'll have the freedom to design an itinerary according to your interests, but there are some regional activities we highly recommend. 

First, you can participate in a Manchego cheese workshop. This cheese is popular around the world, but many don't know that it hails from La Mancha. Made from the milk of the Manchego sheep, it has a buttery texture and comes cured or semi-cured. You'll visit a family-run farm where they still prepare Manchego the same way they did centuries ago. After touring the grounds and seeing the animals and facilities, you'll sit down for a hands-on lesson in 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, who controlled the region in the 10th-12th centuries when La Mancha was the frontier between Christian and Muslim Spain. Here you can visit castles like Calatrava la Nueva and archeological sites like Oreto and Zuqueca, home to the remains of a Visigoth necropolis and an ancient Muslim city.

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

Day 6: Wine Tour of 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 (D.O.) mark of quality, but La Mancha as a whole is the largest continuous wine-growing region in the world. With over 300 vineyards and 22,000 grape growers, you have a lot options for things to do and see here. Luckily you'll have a guide for your excursion into La Mancha wine country.

In the morning you'll meet a wine expert who will take you on a journey into the world of Spanish viticulture. After traveling to a local vineyard, the guide will teach you about the different grape varieties grown in the region. You'll 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 some wines. Popular varietals in La Mancha include Grenache and Tempranillo. 

Then it will be time to eat. You'll be free to choose where to enjoy a traditional La Mancha lunch, and we suggest Villanueva de los Infantes. With its early 17th-century Plaza Mayor (central plaza) and various medieval hermitages and conventsThis throwback 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 home of the title character. 

Plan your trip to Spain
Chat with a local specialist who can help organize your trip.

Day 7: Drive From La Mancha to Córdoba - Guided City Tour

The Mosque-Cathedral of Córdoba
The Mosque-Cathedral of Córdoba

In the morning, you'll embark on a three-hour drive south from La Mancha to Córdoba, and upon arrival, you'll check into your hotel. The perfect antidote to all that driving is to get out and explore. There's quite a bit to see in this city, as it's a historical hodgepodge of Moorish, Gothic, and Jewish architecture. 

On a guided walking tour of Córdoba, you'll visit many amazing sites. This includes the breathtaking Mezquita (Mosque-Cathedral of Córdoba), a pagan temple that was converted into the great mosque of the Ummayad caliphate. Later it was transformed into a Catholic church.

You'll also meander around the winding streets of the Jewish Quarter. Within this historic neighborhood is the Córdoba Synagogue, which dates to 1315. After the expulsion of the Jews from Spain in 1492, the building served different functions. At one time or another, it was a hospital, a chapel, and a nursery school.

In addition, you'll visit the Alcázar de los Reyes, a palace built in the 14th century. This is where Christopher Columbus met with the Catholic monarchs and was granted approval for his voyage west in search of the Indies. The terraced gardens, fish ponds, flower beds, and orange trees here make for great photo opportunities.

Day 8: Drive From Cordoba to Mérida - Lunch in Zafra

The Castle of Zafra
The Castle of Zafra

This morning you'll once again hit the open road, driving about three hours northwest from Córdoba to the city of Mérida. However, about two hours into the journey you'll stop for lunch in the town of Zafra. Known for its gothic castle that dates to 1443, Zafra is a pleasant place to stop for a rest and a bite to eat. You can also take a quick stroll around its famous Plaza Grande and Plaza Chica, two 16th century arcaded squares rimmed by whitewashed buildings, centuries-old homes, and authentic tapas bars. 

After a leisurely lunch, you'll get back on the road and finish the drive to Mérida. This city is the capital of the Extremadura region of west-central Spain, and it has a historic legacy dating back to Roman times. After checking into your hotel you'll have the remainder of the day free to relax.

Day 9: Guided Tour of Mérida

The Roman Theater, Mérida
The Roman Theater, Mérida

You'll begin the day by meeting a local expert guide who will lead you on a walking tour of the city. On this tour, you'll visit Mérida's historic center, which features more extensive Roman ruins than anywhere else in Spain. It's because of these archeological sites that Mérida was declared World Heritage Site by UNESCO in 1986.

Mérida was founded as a Roman colony in the year 25 ACE 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. 

After the barbarians invaded in the fifth century, Mérida became the capital of the Visigoth Kingdom of Hispania. In 713 the city fell in Muslim hands, where it remained until the Christian reconquest in 1230. The tour includes entrance fees to all archeological sites plus the National Roman Art Museum of Mérida. After the tour, you'll return to your hotel and will have the remainder of the day free.

Day 10: Drive from Mérida to Cáceres

The plaza Mayor, Cáceres
The plaza Mayor, Cáceres

Today you'll drive about an hour north from Mérida to the city of Cáceres, which is located in the Cáceres region of Extremadura. Upon arrival, you'll check into your hotel and can then head out on a self-guided tour.

Like Mérida, Cáceres is another historic city with well-preserved Roman roots. It was founded by the Romans in 25 BCE, and after the end of the empire, it fell under the control of the Visigoths before the Moors conquered it in the 8th century. For hundreds of years during the Middle Ages, it changed hands between the Moors and Christians, and you'll see evidence of this history in architecture that runs the gamut from Roman, Moorish, Northern Gothic, and Italian Renaissance.

After spending the day sightseeing, you can enjoy dinner in town. Cáceres is known for its great tapas and cutting-edge culinary scene.

Day 11: Cáceres - Tour Old Town

The Plaza Mayor, Cáceres
The Plaza Mayor, Cáceres

After breakfast, you'll meet your guide for a tour of Cáceres. This city has a rich legacy of conquest and reconquest between the Moors and the Christians. You'll see evidence of this in the architecture, which blends styles from throughout the centuries. It's for these reasons that Cáceres enjoys UNESCO World Heritage status. 

The tour focuses on the Ciudad Vieja (old town) area of the city, which is encircled by defensive walls and home to over 30 different defensive towers. The tour includes a visit to 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 the most beautiful central plazas in all of Spain.

Day 12: Drive to Trujillo - Guided Tour

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 tour.

This incredible town dates back to Roman times yet it's off the tourist trail. As you walk the cobbled streets of Trujillo with your guide, you'll feel like you're stepping back in time. You'll learn all about Trujillo's rich historical legacy (the conquistador Francisco Pizarro was born here) as your guide points 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 views of the town and countryside. 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 13: Day Trip to Monfragüe National Park

Monfragüe National Park
Monfragüe National Park

Within the Extremadura region of Spain lies Monfragüe, a 752-square-mile 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. He or she will lead the way into Monfragüe in a 4x4 vehicle on a guided safari you won't soon forget.

With binoculars in hand, you'll travel through the park, stopping along the way as your guide points out the fauna that calls this area home. These include 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. Throughout the tour, you'll stop at many other stunning viewpoints as well.

As an added bonus, you'll take a break at lunchtime for a picnic amid Monfragüe's unspoiled nature. Afterward, you'll leave the park and transfer back to your hotel.

Day 14: Drive from Trujillo to Madrid - Free Day

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 then 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 some more sightseeing and visit any locales you might have missed your first time around. 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 15: Madrid City Tour - Ham Carving & Flamenco Show

A flamenco  dancer outside Madrid's Royal Palace
A flamenco dancer outside Madrid's Royal Palace

After breakfast, a private guide will pick you up from your hotel and take you on a half-day walking tour of the city. This excursion covers all the highlights from throughout Madrid's long history, from the times of the Habsburgs and the Bourbons to the present day. This, of course, includes a stop at the opulent Royal Palace, which is the former residence of the King and Queen of Spain. You'll also visit the expansive Plaza Mayor, the shopping area along Gran Vía, and a stroll through El Retiro Park, the "green lung" of Madrid. 

The tour culminates with a workshop offering delicious insight into one of Spain's most renowned delicacies: Iberico ham. On a tasting with an expert, you'll learn to differentiate various types of this cured meat as well as how to properly carve it. You'll also learn about the curing process and the pricing structure for the finished product. The tasting experience includes samples of three different hams, all of the highest quality.  

After the workshop, you'll return to your hotel. But don't get too comfortable, as once the sun goes down the fun is only just beginning. In the evening, you'll head near the Royal Palace to the Corral de la Moreria for a flamenco show you won't soon forget.

The Corral might be the most famous tablao (live flamenco venue) in the country. But it's more than a popular dance hall; ever since it opened its doors in 1956 it has hosted performances by some of the most accomplished flamenco performers in the world. This fact has earned it the distinction of being one of the oldest tablaos in the country.

Naturally, this reputation has preceded the Corral, and it is now regarded as one of Madrid's premier evening hot spots. Don't be surprised, then, if you find yourself seated near a visiting international artist, celebrity, or even the King and Queen of Spain.

Day 16: Departure from 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. Adios!


Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 16 days
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 16 days