In less than a week you can visit some of Spain's most historic cities while touring its famed La Mancha region. It begins in Madrid followed by a trip to Toledo, once the capital of Old Spain. You'll then hit the road into La Mancha, enjoying wine tours and stops at the region's famous windmills before returning to Madrid.


  • Tour historic cities like Madrid and Toledo
  • Explore la Mancha on a road trip
  • Take a wine tour of the Valdepeñas region

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Madrid - Evening Tapas Tour Madrid
Day 2 Pick up Rental Car - Drive to Toledo - City Tour Toledo
Day 3 Drive From Toledo to Valdepeñas - Explore La Mancha Valdepeñas area
Day 4 Wine Tour of La Mancha Valdepeñas area
Day 5 Drive to Madrid - Guided Tour Madrid
Day 6 Departure from Madrid  

Detailed Itinerary

Day 1: Arrival in Madrid - Evening Tapas Tour

The Fountain of Cibeles, in Madrid
The Fountain of Cibeles, in 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. 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: Pick up Rental Car - Drive to Toledo - City Tour

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 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. 

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Day 3: Drive From Toledo 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 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 4: Wine Tour of 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 (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 5: Drive to Madrid - Guided Tour

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 walking tour of the city. Along the way, 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.

Day 6: Departure from Madrid

Goodbye, Spain
Goodbye, Spain

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


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