Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 13 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 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.

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 walk in Madrid led by 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. 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, which was the official home of the Spanish monarchs until 1931. You'll explore 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 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 & Explore the City

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. Upon arrival, check into your hotel, which features a breathtaking view of Toledo's city center. In the afternoon, 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 San Juan de los Reyes Monastery, 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 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

After an early breakfast at the hotel, you'll leave Toledo on a 1.5-hour drive south to the town of Almagro, passing 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. 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.

Next, hop back in the car and continue a short way to Almagro, then check into your hotel and explore the village. 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, grand Plaza Mayor, and colonnaded buildings. But the city is most famous for its 16th-century open air-theater, the Corral de Comedias, which is open for daytime tours and evening concerts.

Day 5: Explore La Mancha, Drive to Valdepeñas

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, but there are several regional activities to consider, 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'll visit a family-run farm where they still prepare Manchego the same way they did centuries ago and learn how to make your own 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 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 cemetery and an ancient Muslim city.

Afterward, 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 Excursion in 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. Travel to a local vineyard and 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.

Next, see firsthand the enormous terracotta fermentation containers where the grapes become wine—each one holds an impressive 1,585 gallons (6,000 l)—and sample wines like Grenache and Tempranillo. Then it's 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 convents, this throwback village is straight out of the mind of Cervantes.

After your meal, return to your hotel in wine country and enjoy the remainder of the afternoon at your leisure.

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 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. Visit Mérida's historic center, which features more extensive Roman ruins than anywhere else in Spain. Because of these archaeological sites, UNESCO declared Mérida World Heritage Site 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

Today you'll drive about an hour north from Mérida to the city of Cáceres. Check into your hotel and head out for a self-guided walk.

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. You'll see evidence of this history in architecture 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 9: Explore the Old Town of Cáceres

After breakfast, you'll meet your guide for a history walk of Cáceres in the Ciudad Vieja (old town), encircled by defensive walls and home to over 30 different defensive towers. Enjoy visiting 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 walk, 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 city's Plaza Mayor, one of Spain's most beautiful central plazas.

Day 10: Drive to Trujillo, Guided City Walk

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 an excursion through the historic core. This incredible town dates back to Roman times, with cobbled streets that make you feel like you're stepping back in time. 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.

Visit the major sites in town, including the Plaza Mayor, the city's medieval central plaza with 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. You'll also visit 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 walk also includes a visit to Trujillo Castle, the ninth-century fortress perched on a hill overlooking the town. 

Day 11: Day Trip to Monfragüe National Park

Within the Extremadura region of Spain lies Monfragüe, a national park in the Tagus River Valley. Besides its natural beauty, Monfragüe is known for its exotic birdlife and abundant 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, 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 over the Tagus River. Throughout the day, you'll also stop at many other stunning viewpoints.

As a 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 12: Drive to Madrid, Free Day

After breakfast, you'll hit the road again for the 2.5-hour drive back to Madrid. Upon arrival, 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. 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 13: 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. Adiós!

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