In less than a week, you can visit some of Spain's most historic cities while touring its lesser-known La Mancha region. This road trip begins in Madrid, followed by a trip to Toledo, once the capital of Old Spain. Before returning to Madrid, you'll hit the road and drive into La Mancha, the protagonist's home in "Don Quixote," enjoying wine tours and stops at the region's famous windmills.


  • Enjoy cultural walks through historic cities like Madrid and Toledo
  • Explore the arid plateau of La Mancha on a road trip
  • Discover the delicious and unique wine of the Valdepeñas region

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Madrid, Evening Tapas Experience Madrid
Day 2 Pick up Rental Car & Drive to Toledo, City History Walk Toledo
Day 3 Drive to Valdepeñas, Explore La Mancha Valdepeñas
Day 4 Wine Excursion in La Mancha Valdepeñas
Day 5 Return to Madrid, Guided City Walk Madrid
Day 6 Depart Madrid  

Detailed Itinerary

Day 1: Arrive in Madrid, Evening Tapas Experience

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 its 18th-century sculpture 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 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 sites 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: Pick up Rental Car & Drive to Toledo, City History 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 road trip. The first stop is the city of Toledo, located about an hour south of Madrid. Upon arrival, you'll 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 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. 

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Day 3: Drive to Valdepeñas, Explore La Mancha

The famous windmills of La Mancha
The famous windmills of 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 be free to design an itinerary according to your interests, but there are some excellent 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'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 on 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, 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. Then, continue to your hotel in the rural wine-producing region of Valdepeñas in southern La Mancha. 

Day 4: 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 also the world's largest continuous wine-growing region, with over 300 vineyards and 22,000 grape growers. Learn about the different grape varieties grown in the region, the 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. 

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). Then, sample some wines, including popular La Mancha varietals like Grenache and Tempranillo. 

Now, 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 convent 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 5: Return to Madrid, Guided City Walk

The Royal Palace, Madrid
The Royal Palace, Madrid

In the morning, you'll drive from La Mancha north to Madrid and check into your hotel. Spain has a long and storied history, and today the city adorns itself with that legacy in its architecture, public spaces, and culture. You'll discover this on a three-hour guided walk in the city. Along the way, your guide will reveal how different time periods influenced Madrid's neighborhoods and buildings and point out the most interesting sites.

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, 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.

Day 6: Depart Madrid

Goodbye, Madrid
Goodbye, Madrid

It's time to say farewell. After a leisurely breakfast, you'll transfer to the airport to catch your flight. This concludes your great Spanish adventure for now. Adiós!


Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 6 days
Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 6 days