Ultimate Southern Spain Road Trip: Madrid, La Mancha & Andalusia - 16 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 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 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 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 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 visit 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, 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

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 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 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 Valdepeñas, Guided Excursion in La Mancha

In the morning, you'll embark on an exploration of La Mancha. First, you'll drive to the town of Madridejos and visit a museum dedicated to saffron. The saffron produced in La Mancha is considered to be some of the best in the world. The museum is located in a former convent and features exhibits detailing the production process, from preparing the land and planting the seeds to the harvest and peeling the saffron rose before drying, cutting, and partitioning it for sale.

After Madridejos, you'll drive to the town of Consuegra. This was the home region 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 visit them on a guided excursion. You'll also visit Castillo de la Muela, a well-preserved castle that dates to the 10th century.

Later in the afternoon, you can participate in a Manchego cheese workshop. This cheese is popular worldwide, but many don't know it's from La Mancha. Made from the Manchego sheep's milk, it has a buttery texture and comes cured or semi-cured. This workshop includes a visit to a family-run farm and a hands-on lesson. Afterward, you'll continue the drive to Valdepeñas and check into your hotel. You'll have the remainder of the day free to relax.

Day 5: Drive to Córdoba, Wine Experience

Today you'll embark on a  drive from La Mancha to Córdoba, in Spain's Andalusia region. First, enjoy a wine tour of 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. 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 L). 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. Then continue your drive to Córdoba.

Day 6: Private City Walk in Córdoba

In the morning, you'll meet your private guide for a walk around Córdoba's city center. You'll visit all the amazing sites, including the breathtaking Mezquita (Mosque-Cathedral of Córdoba), a pagan temple that was converted into the great mosque of the Ummayad caliphate and later transformed into a Catholic church. You'll also visit the Alcázar de los Reyes, a palace built in the 14th century. The terraced gardens, fish ponds, flower beds, and orange trees here make for great photo opportunities. 

You'll also have the option to meander around the winding and narrow streets of the historic Jewish Quarter. At the end of the walk, your guide will say farewell and leave you in a popular local restaurant for a typical Córdoban lunch. The afternoon is then yours to continue exploring the city at your leisure. In the evening, you'll meet up with your guide again for a gastronomic experience as you visit markets and bars, pairing Spanish tapas with the perfect local wines. 

Day 7: Drive to Seville, Tapas Experience

After breakfast, you'll hit the road again for a two-hour drive west from Córdoba to Andalusia's capital, Seville. You can stop along the way to snap photos at historic sights like the medieval Castle of Almodóvar del Río or the village of Palma del Rio. Upon arrival in Seville, you'll check into your hotel in the city center.

Then, in the evening, it will be time to eat. You'll head to Seville's historic Old Town for an evening of delicious tapas with an expert guide who will lead you to two family-run taverns and recommend a wide selection of dishes. Enjoy the experience like a local, trying authentic tapas like acorn-fed Iberian ham, gambas al ajillo (garlic shrimp in oil), and bacalao (salt cod). Of course, throughout the dinner, you'll pair the tapas with delicious local wines. 

Day 8: Half-Day City Walk in Seville

After breakfast, you'll head off with a local guide to explore Seville. Start with the Seville Cathedral, a 15th-century Roman-Catholic church that's home to the tomb of Christopher Columbus. You'll also see La Giralda, which is the cathedral's looming bell tower. There's a noticeable stylistic difference between the two structures, as this 12th-century pillar was originally built as a minaret for the Great Mosque back when the Moors ruled Andalusia.

You'll also visit the Alcázar of Seville, a royal palace commissioned for King Peter of Castile in the 14th century, built over the site of a former Muslim fortress. It features well-manicured gardens, and the building is one of the nation's finest examples of Mudéjar architecture. Walk to the fashionable Santa Cruz neighborhood, which was once the Jewish Quarter in the city. It's a colorful and well-preserved part of the historic center, with many options for cafés and tapas bars.

After completing the half-day excursion, you can return to your hotel and relax or continue to explore the town. If you decide to head out in the evening, do like the locals and complement tapas with a nightcap at a favorite watering hole.

Day 9: Day Trip to Jerez, Sherry Tasting & Dancing Horses

This morning, you'll make the short drive to the Moorish town of Jerez de la Frontera, famous for sherry wine production. It's also home to the Royal Equestrian Academy, one of the premier riding schools in the country. The horse-racing culture in this region runs deep and dates back to the earliest days of Muslim rule in Spain.

You'll arrive in Jerez's historic Old Town, which is centered around the dominating Alcázar, an 11th-century Moorish fortress. Here you'll meet an expert guide and explore the town highlights. You'll also visit a local sherry bodega (winery) for a tasting, sampling several types of local sherry, all paired with delicious tapas. As an added bonus, the bodega keeps a collection of original Picasso artwork on hand that you can admire.

Next, discover the equine culture of Jerez with a live Andalusian horse performance. The show, "How Andalusian Horses Dance," features prized horses performing various types of dressage: classic, carriage, vaquera, etc. The show represents how countryside horsemanship has risen over the millennia to become an art form. Afterward, hop back in the car and return to Seville. You'll have the remainder of the day free to enjoy the city.

Day 10: Drive to Ronda via Arcos de la Frontera

After breakfast in Seville, you'll embark on a road trip through some of Andalusia's most enchanting locales. Take in the views as you drive through olive groves, rolling meadows, cork forests, and around mountains, passing the region's famous "White Villages"—ancient hilltop towns famous for their whitewashed buildings.

Your destination is Ronda, a historic city located atop a gorge in the Málaga province. It's about a two-hour drive south from Seville to Ronda, but you'll stop along the way in Arcos de la Frontera, one of the aforementioned white villages. With an expert guide, you'll meander the narrow cobbled streets, marveling at the Moorish towers and castles that rise up between the white buildings. Even better, there are many points in town where you can enjoy sweeping vistas of the Andalusian countryside below.

After the walk, you'll stop at a local restaurant for a traditional Andalusian lunch paired with local wines. You'll then continue on to Ronda, arriving in the afternoon. After checking in to your hotel, you'll have the rest of the day free.

Day 11: Drive to Granada via the Caminito del Rey

After breakfast, you'll meet your guide and set off on an outing in Ronda. The excursion includes a visit to the spectacular Bullring of the Royal Cavalry of Ronda, largely considered one of the most important in Spain. You'll also stop at numerous buildings, churches, convents, and palaces belonging to a long and illustrious Roman and Moorish history.

Once the tour ends, hop in the car and set off to the city of Granada, located about two hours east of Ronda. Along the way, stop for an adrenaline-pumping hike at the Caminito del Rey—a stunning network of walkways built along a deep gorge carved out by the Guadalhorce River. After putting on your safety equipment, you'll start the hike and enjoy incredible views down the gorge to the river. This one-way trail typically takes about three to four hours to complete.

Afterward, you'll continue the rest of the way to Granada, where you'll check into your hotel and have the rest of the day to relax and recharge.

Day 12: Private Experience in the Alhambra & Generalife Gardens

When the Moors ruled the region, Granada was the last bastion of Al-Andalus (Muslim Spain). You can see examples of this history in the form of Granada's most famous landmark, the Alhambra, which receives more than two million visitors annually. In the morning, you'll meet an expert guide for a private visit.

This imposing ninth-century Muslim fortress was built atop a hill overlooking Granada and rebuilt in the 14th century by the Nasrid Dynasty. It served as a Moorish palace until 1492, when after the Christian reconquest, it became the Royal Court of Ferdinand and Isabella. It's now a UNESCO World Heritage Site. You'll walk through its grand halls and stroll the Generalife Gardens, filled with colorful flowers and fountains that offer panoramic views of the city.

Afterward, you'll have free time to enjoy Granada on your own. You can walk around the labyrinthine streets of the Albayzin and Sacromonte quarters, the well-preserved historic neighborhoods of the city. In areas such as these, you can visit the Granada Cathedral, Royal Church, Alcaicería (old silk market), and Madraza (medieval Koranic school).

Day 13: Day Trip to Andalusian Countryside, Tapas Cooking Class

Today you'll drive half an hour from Granada to the Lecrin Valley in rural Andalusia. Situated at the base of the Sierra Nevada Mountains, the Lecrin Vallery enjoys a gentle microclimate ideal for growing citrus fruits, almonds, and olives. On a half-day excursion, you'll explore this delightful countryside with a British couple living in a farmhouse surrounded by orange groves with stunning views over the valley. 

You'll head to the farmhouse at lunchtime for a traditional country meal of homemade tapas. Upon arrival, you'll enjoy a specially prepared tasting menu of regional dishes accompanied by a selection of wines from Granada Province. After lunch, you can rest in the farm's garden or stroll through the olive and orange groves before you return to Granada.

Day 14: Drive to Málaga

After a leisurely breakfast, you'll get in the car and drive 1.5 hours from Granada to Málaga. This port city has been rejuvenated over the last few years and is quickly becoming a hotbed of culture, style, and art. Speaking of which, art buffs will be interested to know that Málaga is the birthplace of perhaps the greatest artist of the 20th century, Pablo Picasso.

Upon arrival in Málaga, you'll check into your hotel and take some time to settle into your accommodation before heading out to explore. The first order of business can be to sample Málaga's delectable cuisine. You'll find plenty of great eateries in the neighborhoods near the waterfront and along Calle Marques de Larios. You'll also notice certain common ingredients used in the cuisine of Málaga, which include olives, almonds, grapes, and raisins.

Day 15: Private Walk in Málaga, Visit the Picasso Museum

This morning, you'll meet a local expert guide and embark on a walk through Málaga. The city is fast growing in popularity and offers a buzzing atmosphere and a wealth of things to see and do. Your guide will tell you all about Málaga's history, stopping by spots such as the Plaza de la Constitución, the Roman Theatre, the Cathedral of Málaga, and the Central Market. You'll also visit the birthplace of Pablo Picasso.

Afterward, your guide will lead you to the Picasso Museum. Here you'll find an impressive collection of paintings, ceramics, graphic art, and illustrated books next to personal memorabilia of the family of Picasso. The museum offers an intimate look at the cubist master and, through various exhibits, showcases the changes in his artistic style throughout his legendary career.

Day 16: Depart Spain

It's time to say farewell! Depending on the time of your flight or train reservation, squeeze in one more walk through the streets of Málaga, perhaps picking up some last-minute souvenirs. At the designated time, you will be picked up at your hotel and transferred to the airport or rail station for your departure. Safe travels!

More Great Spain Itineraries

Looking for more inspiration for your trip to Spain? Check out these other road trips in Spain, explore different ways to spend 16 days on the road in Spain, or discover the best time to visit Spain.