Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 10 days

Day 1: Arrival in Madrid - Evening Tapas Tour

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

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

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 Valdepeñas - Explore La Mancha

In the morning, you'll hop back in the car and drive south from Toledo for a 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 5: Wine Tour 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. 

Day 6: Drive From La Mancha to Mérida - Guided City Tour

This morning you'll once again hit the open road, driving about 3.5 hours west from La Mancha 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 meet 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. 

Day 7: Drive from Mérida to Cáceres - Tour Old Town

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, it was controlled by 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, as evidenced by architecture that runs the gamut from Roman, Moorish, Northern Gothic, and Italian Renaissance.

After checking into your hotel, you'll meet an expert guide for a city tour. Cáceres 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 8: Drive to Trujillo - Guided Tour

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 9: Drive to Madrid - Stop at Monfragüe National Park

In the morning, you'll get back in the car and continue the drive about 2.5-hours northwest to Madrid. However, you'll break up the journey by stopping in Monfragüe National Park for a photo safari.

Monfragüe is a 752-square-mile national park in the valley of the Tagus River in Spain's Extremadura region. Besides its natural beauty, the park is known for exotic birdlife and an abundance of wild animals. Upon arrival at the entrance to the park, you'll meet an expert naturalist who will be your guide/driver. 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 continue on to Madrid, where you'll check into your hotel.

Day 10: Departure from Madrid

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!

Looking for more Spain self-drive itineraries? Check out kimkim's guide to the top 10-Day road trips in Spain.