Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 11 days

Day 1: Arrive in Madrid, Evening Tapas Experience

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 city's most historic and expansive plazas. There's also Madrid's famous Fountain of Cibeles featuring an 18th-century sculpture completed 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 sights 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

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 architecture, public spaces, and culture that reflect its past. An organized walk is ideal, and your guide will reveal insight into how different time periods influenced Madrid's neighborhoods and buildings and point out the most interesting sights.

One area you'll visit that's awash in splendor is the Madrid de los Austrias, home to one of the grandest plazas in Spain, the Plaza Mayor, which was once the heart of Old Madrid. Another highlight is 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 of opulence, 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. This 308-acre (125 ha) 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 is from May through June. 

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

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 settling into your hotel, 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.

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 excursion 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 4: Drive to Almagro via Las Tablas de Daimiel

After an early breakfast at the hotel, you'll leave Toledo on a 1.5-hour drive south to the town of Almagro. Make a pit stop in 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 excursion through Spain's smallest natural park, home to various migratory waterbirds, like herons and egrets, who flock to these expansive wetlands during winter.

Next, hop back in the car and continue to Almagro, where you'll check into your hotel and enjoy a free evening. Almagro has well-preserved 15th-century architecture thanks to its aristocratic culture, which you can see in the stately manor homes and grand Plaza Mayor 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 it features performances from Spain's golden age of theater of the 16th and 17th centuries.

Day 5: Explore La Mancha, Drive to Valdepeñas

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 highly recommended regional activities, such as 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 Manchego sheep's milk, it has a buttery texture and comes cured or semi-cured. You can visit a family-run farm that uses traditional techniques, tour the grounds, and enjoy a cheesemaking workshop.

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 archaeological 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 in southern La Mancha. After checking in, you can spend the remainder of the day relaxing.

Day 6: Wine Tour 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. After traveling to a local vineyard, you'll discover different grape varieties grown in the region, the techniques that go into harvesting grapes on a small-production vineyard, and external factors that 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 l). Then, sit down to sample some wines, including Grenache and Tempranillo, popular varietals in La Mancha.

Now it's time to eat. You can 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 convents, this 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 title character's home. 

Day 7: Drive to Mérida, Guided City Walk

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 the Extremadura region of west-central Spain, and it 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 excursion, you'll visit Mérida's historic center, which features more extensive Roman ruins than anywhere else in Spain. Because of these archaeological sites, 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, Stroll the 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, founded in 25 BCE, and after the end of the empire, controlled by the Visigoths before the Moors conquered it in the eigth century. During the Middle Ages, it changed hands between the Moors and Christians for hundreds of years, as evidenced by architecture that runs 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 UNESCO World Heritage status and a rich legacy of conquest and reconquest between the Moors and the Christians. You'll see evidence of this in the architecture within the Ciudad Vieja (old town), encircled by defensive walls and home to over 30 different towers. You'll also visit the Torre Bujaco, an Arab tower claimed by Ferdinand II of León in 1170 but retaken by the Moors in 1173.

Throughout the rest of the outing, 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 Experience

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 walk, learning 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 structure 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 ninth-century fortress that's perched on a hill overlooking the town. 

Day 10: Drive to Madrid via 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 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.

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. You'll also stop 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 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 11: Depart 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!

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