Best of Toledo

Top itineraries and travel advice in and around Toledo

Perched on a hill and surrounded by a gorgeous landscape, Toledo is easily one of the most beautiful small cities in Spain. Toledo is full of picturesque streets and architecture - in fact, the entire city is a UNESCO World Heritage site due to its large number of historical monuments.

Toledo's history dates back to Roman times, but in the 16th century, the city was the capital of Old Spain. It was during this period that Toledo 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 history in the monuments created by all three groups that still stand. These include the 15th-century Monastery of San Juan de Los Reyes, the Mosque-Church of El Salvador, and the Synagogue of Santa María la Blanca, which dates to the 12th century.

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The Best Things to Do in Madrid

Many argue that Madrid is Spain's most cultural city, as its central location draws people, gastronomy, traditions, and customs from around the country. In Madrid, you can dive deep into Spain's history and culture with walking tours of its diverse neighborhoods, evenings experiencing its distinct tavern culture, and tastes of staples like jamón Ibérico and padrón peppers. Then, peruse the world-renowned Prado Museum, enjoy dinner in the world's oldest restaurant, learn all about Spanish royalty, or take a day trip to one of the nearby historic cities and villages.

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

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.

Discover the 9th century Alhambra Palace in Granada

Highlights of Central and Southern Spain: Madrid, Seville, & Barcelona - 12 Days

This complete 12-day itinerary highlights some of Spain's most enchanting cities, featuring Madrid, Sevilla, and Barcelona. Begin in Madrid and explore historic Toledo, working your way into Andalucía and to Sevilla, Córdoba, Arcos de la Frontera, Ronda, and Granada. Fly to Barcelona and discover Gaudí's whimsical architecture, the 1000-year-old abbey in the Montserrat mountains, and the wines of the Penedès region.

Ultimate Southern Spain Road Trip: Madrid to Andalusia - 9 days

Due to its abundance of natural beauty and historic cities, Spain's southern Andalusia region is perfect for a road trip. This nine-day self-drive adventure begins in Madrid and includes a stop in Toledo, one of the most well-preserved medieval cities in Spain. Upon arrival in Andalusia, you'll visit cities like Córdoba and the capital of Seville for tapas tours and visits to Moorish landmarks.

Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 9 days

See a different Spain on a nine-day road trip that takes you from Madrid south to the arid plateau region of La Mancha. This land of Don Quixote is a major wine-producing region, which you'll discover on a tasting tour. You'll also visit historic medieval towns like Villanueva de los Infantes and the romantic waterfalls of Ruidera Lakes.

Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 10 days

Over 10 days you'll leave the tourist traps and discover the real Spain, the ancient Spain—Don Quixote's Spain. From Madrid, you'll embark on a road trip into the plateau region of La Mancha, famous for its medieval towns, national parks, and vineyards. By the time the adventure ends, you'll have experienced a region that has captivated the world ever since Spain's golden age of literature.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 10 days

Get lost in La Mancha on a 10-day road trip in this historic region in central Spain. It begins in Madrid and from there you'll travel south to the arid plateaus famous for being the homeland of the fictional character Don Quixote. Between wine tours and visits to national parks, you'll head to the Extremadura region and tour medieval cities like Cáceres, birthplace of the conquistador Francisco Pizarro.

Ultimate Southern Spain Road Trip: Madrid to Andalusia - 11 days

The best way to see the most historic sights in Spain is on a road trip. This 11-day self-drive adventure begins with city tours in Madrid, and then you'll hop in your car and head south to Toledo, once the capital of the nation in the Middle Ages. You'll continue to Andalusia and marvel at the region's Moorish alcázars and royal palaces while also stopping in historic cities like Córdoba.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 11 days

An adventurous alternative to the popular beach holidays and major city tours of Spain is to embark on a road trip through La Mancha. This plateau south of Madrid is a vast and beautiful expanse filled with castles, vineyards, and medieval towns. After experiencing La Mancha's highlights, you'll continue to western Extremadura and tour historic cities like Mérida and Cáceres.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 12 days

Spain is filled with historic regions abounding with well-preserved ancient cities, like La Mancha. This dry plateau region is located south of Madrid, and you'll discover its historic and literary legacy (it's Don Quixote's home region) on a self-drive road trip. Along the way, you'll imbibe in La Mancha's wine, visit its national parks, and travel further west, to Extremadura and medieval cities like Mérida and Cáceres.

Ultimate Southern Spain Road Trip: Madrid to Andalusia - 13 days

Get ready for an unforgettable road trip through southern Spain that takes in many of the nation's highlights. The adventure begins with city tours of Madrid before hitting the road south, stopping in La Mancha and Córdoba before reaching Seville, capital of the Andalusia region. You'll visit historic Moorish and medieval landmarks, tour authentic tapas bars, and even hike along the side of a gorge near Ronda.

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

You're in for a treat because over 13 days you'll discover historic Spain, colonial Spain—the Spain of conquistadores and Cervantes. It's a road-trip adventure that begins amid the windmills of La Mancha, home region of Don Quixote. After wine tours and visits to national parks, you'll tour medieval cities of the Extremadura region like Cáceres, the birthplace of Francisco Pizarro.

Ultimate Southern Spain Road Trip: Madrid, La Mancha, & Andalusia - 14 days

In two weeks you can enjoy a road trip that takes you to some of the most historic and beautiful locales in Spain. It begins in Madrid, and from there you'll travel south through La Mancha into Andalusia and visit Moorish cities like Granada, Ronda, Córdoba, and Málaga. But that isn't all—you'll also enjoy wine and sherry tours, eat delicious tapas, and even witness a traditional equestrian show.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 14 days

Just south of Madrid is a wildly beautiful region little-visited by tourists in Spain. This is La Mancha, an arid plateau famous as the home of Cervantes' legendary protagonist, Don Quixote. Fables aside, La Mancha is real, and on a road trip you'll discover its fertile vineyards and unspoiled national parks plus the well-preserved medieval cities of Spain's western Extremadura region.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 15 days

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.

Ultimate Southern Spain Road Trip: Madrid, La Mancha, & Andalusia - 15 days

It's almost impossible to design a more comprehensive Spanish holiday than this 15-day road trip. Beginning in Madrid, you'll drive south to historic locales like Toledo and La Mancha on your way to Andalusia, where Moorish history and amazing food await. Besides enjoying wine and tapas tours, you'll visit incredible cities like Seville, Granada, Ronda, and Córdoba.

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

This comprehensive 16-day road trip includes all the highlights of Spain's Andalusia region, from the capital of Seville to the Moorish palaces of Granada and even the coastal retreat of Málaga, birthplace of Pablo Picasso. As an added bonus you'll also visit La Mancha, an arid plateau region home to great wine and historic villages.

Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 16 days

Get ready to travel the route of Don Quixote on a road trip through Spain. It begins with a city tour of Madrid before you hit the road, driving amid the arid plateaus and windmills of La Mancha and into the Extramadura region of western Spain. Here you'll tour historic towns like Cáceres and Trujillo while sampling delicious local cuisine and visiting unspoiled national parks.

Cities & Culture in Spain: Madrid, Seville, & Granada - 9 Days

This 9-day road trip includes stops at some of Spain's most historic locales, including Madrid, Toledo, and the Andalusian cities of Seville and Granada. Celebrate rich Spanish culture as you tour historic Old Towns by foot and bike, all while tasting delicious tapas and enjoying a flamenco show. You'll explore the southern countryside with a tour of an olive oil farm and a hike along Caminito del Rey, and then visit Granada to discover one of the most impressive Moorish palaces in Europe, the Alhambra.

Highlights of Spain, from Barcelona to Andalusia - 16 Days

This tour takes you from the unique architecture of Antoni Gaudí in Barcelona to the vibrant streets of Madrid, finishing in the historic region of Andalusia in Spain's south. Along the way, visit the cities of Segovia and Toledo, as well as Ronda and the traditional white villages of Grazalema and Zahara de la Sierra, including a hike along the Caminito del Rey. Enjoy a guided visit through the Alhambra in Granada, and ample time to explore Córdoba, Seville, and Cádiz on your own, all while enjoying traditional tapas, local wine, and a flamenco show.

Highlights of Madrid and Andalusía - 8 Days

Explore the highlights of Spain by visiting the cities of Madrid, Córdoba, and Granada on this 8-day trip. You'll enjoy private tours of the historic old towns, as well as a day trip to Toledo to learn about its historic steel production and marzipan. End the trip in Spain's southern region Andalusía with tours of the Alhambra in Granada, the Mezquita in Córdoba, and the famous White Villages in the countryside.

Other popular travel destinations in Spain
Madrid · Andalusia · Catalonia · Barcelona · Seville · Granada · Basque Country · Córdoba · Balearic Islands · Canary Islands · La Mancha · Costa Brava · Mallorca · Santiago de Compostela · Ibiza · La Rioja · Pamplona · Marbella

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