This 15-day road-trip adventure allows you to experience regions of Spain most tourists never see. It begins in Madrid, and you'll quickly hit the road south to La Mancha, the land of Don Quixote, windmills, arid plains, and stunning national parks. From there, you'll head west to the Extremadura region, home to some of the most well-preserved medieval towns in the country.


  • See the most famous sights of Madrid on a guided walk
  • 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 Arrive in Madrid, Evening Tapas Walk 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 Mérida
Day 8 Guided Walk in Mérida Mérida
Day 9 Drive to Cáceres Cáceres
Day 10 Cáceres Old Town Walk Cáceres
Day 11 Drive to Trujillo, Guided Walk Trujillo
Day 12 Day Trip to Monfragüe National Park Trujillo
Day 13 Drive to Madrid, Free Day in the City Madrid
Day 14 Madrid City Walk, Jamón Carving & Flamenco Show Madrid
Day 15 Depart Spain  

Detailed Itinerary

Day 1: Arrive in Madrid, Evening Tapas Walk

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

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, which was 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 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 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 along 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 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, continue to Almagro and check into your hotel. This town abounds with rich history and beautiful landmarks. Its well-preserved 15th-century architecture pays homage to the town's aristocratic culture, with 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 day tours and evening performances.

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 participate in a Manchego cheese workshop, a product popular around the world that many don't know comes 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, see the animals, and enjoy a cheesemaking class.

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 necropolis and an ancient Muslim city.

After touring around the region, 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.

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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 the 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 some wines, including 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. 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

Plaza Grande, Zafra
Plaza Grande, Zafra

This morning you'll once again hit the open road, driving about 3.5 hours west from La Mancha to the city of 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 have the remainder of the day free to relax and explore the city.

Day 8: Guided Walk in 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 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.

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

Day 9: Drive 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 Extremadura. Upon arrival, check into your hotel, settle in, and then head out on 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 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 10: Cáceres Old Town Walk

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. The excursion focuses on the Ciudad Vieja (old town), encircled by defensive walls and home to over 30 different defensive towers. The walk 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 day, 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 11: 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 walk in the town, which dates back to Roman times, yet is off the tourist trail. As you walk the cobbled streets of Trujillo, you'll feel like you're stepping back in time. Learn all about the town'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.

You'll visit the major sites, 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 12: 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. Enjoy exploring Monfragüe in a 4WD vehicle on a guided safari.

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 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 13: 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, check into your hotel and then return your rental car. You'll 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 to 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 14: Madrid City Walk, Jamón 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 walk through the city. This excursion covers all the highlights from Madrid's long history, including a stop at the opulent Royal Palace, 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 El Retiro Park.

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 carve it properly. You'll also learn about the finished product's curing process and pricing structure. The tasting experience includes samples of the highest quality of three different hams. 

After the workshop, return to your hotel. Then, 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.

Day 15: Depart Spain

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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