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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Madrid, Spain
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.

Enjoy visiting scenic and historical cities, including Toledo, once the capital of Old Spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 6 days
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 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.

Visit the incredibly historic Alhambra Palace in Granada, Spain
Map of Ultimate Southern Spain Road Trip: Madrid to Andalusia - 12 days
Ultimate Southern Spain Road Trip: Madrid to Andalusia - 12 days

Enjoy a road trip through Spain that takes you from Madrid to Málaga through Toledo and the three jewels of Andalusia: Córdoba, Seville, and Granada. Beyond the cities, you'll enjoy cultural excursions like sherry wine tastings and horse competitions. And at each destination, you'll meet a private guide who will reveal the hidden treasures of these historic and beautiful locales.

Learn to make the perfect paella with a family cooking class in Madrid
Map of Family Adventures in Spain: Madrid, Toledo & Seville - 8 Days
Family Adventures in Spain: Madrid, Toledo & Seville - 8 Days

Kick off this eight-day, family-focused tour in historic Madrid, where you'll learn to make traditional paella in a family cooking class and take lessons in the art of flamenco, Spain's most famous dance! Spend some time in Toledo to discover the art of sword-making with a master craftsperson, then head to Seville for a luxurious river cruise and a creative pottery class. See the Seville Cathedral and Royal Alcázar with a private guide, and spend your last evening eating your way through the city's best tapas restaurants.

Discover the 9th century Alhambra Palace in Granada
Map of Highlights of Central and Southern Spain: Madrid, Seville, & Barcelona - 12 Days
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.

Spain
Map of Ultimate Southern Spain Road Trip: Madrid to Andalusia - 9 days
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 stops in Toledo, one of Spain's most well-preserved medieval cities. In Andalusia, you'll visit cities like Córdoba and the capital of Seville for tapas tours and visits to Moorish landmarks. 

Rudiera Lakes in La Mancha, Spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 9 days
Spain Off-the-Beaten-Path Road Trip: Madrid to La Mancha - 9 days

See a different side of Spain on a nine-day road trip that takes you from Madrid 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 excursion. You'll also visit historic medieval towns like Villanueva de los Infantes and the romantic waterfalls of Ruidera Lakes.

See the top sights in Madrid with your family
Map of Family Adventures in Spain: Madrid, Toledo & Seville - 9 Days
Family Adventures in Spain: Madrid, Toledo & Seville - 9 Days

This family-friendly tour of Spain starts in the capital city of Madrid, where you'll make traditional paella, visit the historic Plaza Mayor, and learn the art of flamenco, Spain's most famous dance! Take a day trip to Segovia for breathtaking views via hot-air balloon and spend some time with the master swordsmiths of Toledo. Then, it's off to picturesque Seville for a cruise on the Guadalquivir River, pottery classes in the artsy Triana district, and the gastronomical wonders of Andalusia's tapas restaurants.

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

The famous windmills of Consuegra, Spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha, & Extremadura - 10 days
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.

Views of the canyon from atop El Tajo Gorge in Ronda, Spain
Map of Ultimate Southern Spain Road Trip: Madrid to Andalusia - 11 days
Ultimate Southern Spain Road Trip: Madrid to Andalusia - 11 days

A road trip is the best way to see the most historical sites in Spain. 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.

Stroll through the historic streets of towns like Trujillo, Spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 11 days
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.

Broaden young palates with family cooking classes and tapas tours
Map of Family Adventures in Spain: Madrid, Toledo, Córdoba & Seville - 11 Days
Family Adventures in Spain: Madrid, Toledo, Córdoba & Seville - 11 Days

See Spain's top sights from Madrid to Andalusia on this 11-day family tour. Start in the capital to stroll the lively Plaza Mayor, prepare (and eat!) delicious paella, and learn the art of flamenco. Visit Toledo and watch swordsmiths at work, then it's off to Córdoba to see the Moorish architecture of the Mezquita and take a horseback ride through the nearby countryside. End your adventure in Seville, exploring the Royal Alcázar, relaxing on a scenic river cruise, and getting crafty with a pottery workshop.

Discover the iconic windmills of La Mancha, Made famouse by Cervantes' "Don Quixote"
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 12 days
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 historical 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 farther west to Extremadura and medieval cities like Mérida and Cáceres. 

Watch the sunset over Córdoba's famed Roman bridge
Map of Ultimate Southern Spain Road Trip: Madrid to Andalusia - 13 days
Ultimate Southern Spain Road Trip: Madrid to Andalusia - 13 days

Prepare for a memorable road trip through southern Spain, emphasizing 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, the 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.

Extremadura and the Tajo River in Monfragüe National Park
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 13 days
Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 13 days

Over 13 days, you'll discover historic Spain, the Spain of conquistadores and Cervantes. It's a road-trip adventure that begins amid the windmills of La Mancha, the home region of "Don Quixote." After wine excursions and visits to national parks, you'll explore medieval cities of the Extremadura region, including Cáceres, the birthplace of Francisco Pizarro.

Start your adventure in Madrid with your family
Map of Family Adventures in Spain: Madrid, Toledo, Cordoba & Seville - 13 Days
Family Adventures in Spain: Madrid, Toledo, Cordoba & Seville - 13 Days

This 13-day family adventure starts in the capital city of Madrid, where you'll stroll through the vibrant Plaza Mayor, learn to make traditional Spanish paella, and show off your dancing skills in a flamenco class. Head to Toledo to see swordsmiths at work, then it's off to Córdoba for a family tour of the impressive architecture of the Mezquita Cathedral. Learn to make Triana pottery and cruise the Guadalquivir River in Seville, and end your trip with a relaxing visit to the gorgeous beaches of Málaga.

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Map of Ultimate Southern Spain Road Trip: Madrid, La Mancha & Andalusia - 14 days
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. You'll also enjoy wine and sherry excursions, eat delicious tapas, and even witness a traditional equestrian show.

spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 14 days
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. On a road trip, you'll discover its fertile vineyards, unspoiled national parks, and the well-preserved medieval cities of Spain's western Extremadura region.

Spend four days exploring the Balearic island of Menorca by Jeep and catamaran
Map of Luxury Spain Getaway: Madrid to the Mediterranean - 14 Days
Luxury Spain Getaway: Madrid to the Mediterranean - 14 Days

Discover Spain’s showstopping highlights on this luxury two-week tour. You’ll stay in 5-star hotels and restored palaces, joining private guides for cultural tours of Madrid, Granada, and Barcelona. Exclusive experiences include flamenco performances, marzipan workshops, and Michelin-starred dining. Take day trips to Penedès vineyards and the Alpujarras Mountains, then jet to the sun-blessed island of Menorca, where white-sand beaches, catamaran tours, and Jeep safaris await.

Iglesia San Martín, a 16th-century church in Trujillo, Spain
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 15 days
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.

Relax in the courtyard of Córdoba's Mosque-Cathedral
Map of Ultimate Southern Spain Road Trip: Madrid, La Mancha & Andalusia - 15 days
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.

See historic cities, natural highlights and plenty of beaches on this family adventure
Map of Epic Family Adventure in Spain: Madrid, Toledo, Córdoba, Málaga & Barcelona  - 15 Days
Epic Family Adventure in Spain: Madrid, Toledo, Córdoba, Málaga & Barcelona - 15 Days

This 15-day family exploration of Spain starts in historic Madrid, where you'll stroll the lively Plaza Mayor, prepare (and eat!) delicious paella, and learn the art of flamenco. Visit Toledo and watch swordsmiths at work, then head to Córdoba for the Mezquita's stunning Moorish designs and a horseback ride through the nearby countryside. Cruise the Guadalquivir River in Seville, swim and surf on the beaches of Málaga, and end with a tour of Gaudí 's whimsical architecture in Barcelona.

The Alhambra in Granada Spain
Map of Ultimate Southern Spain Road Trip: Madrid, La Mancha & Andalusia - 16 days
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, the 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.

Discover the land of "Don Quixote" (and its famous windmills) in Spain's La Mancha region
Map of Spain Off-the-Beaten-Path Road Trip: Madrid, La Mancha & Extremadura - 16 days
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 Extremadura region of western Spain. Here you'll tour historic towns like Cáceres and Trujillo while sampling delicious local cuisine and visiting unspoiled national parks.

Take the ultimate Spain vacation with your family
Map of Epic Family Adventure in Spain - 16 Days
Epic Family Adventure in Spain - 16 Days

You'll find culture, history, and plenty of interactive fun on this kid-friendly 16-day trip to Spain. Touch down in Madrid, where the whole family can roll up their sleeves to learn how to make paella and brush up on their flamenco steps. Take to the skies over Segovia by hot-air balloon, play swordsmiths for the day in Toledo, explore the Moorish palaces of Córdoba, and learn to make pottery in Seville. After an epic treasure hunt and plenty of beach time in Málaga, wind down in Barcelona with a sunset sailing trip.

The Alhambra and Generalife, Granada
Map of Highlights of Madrid & Andalusía - 8 Days
Highlights of Madrid & Andalusía - 8 Days

Explore the highlights of Spain by visiting the cities of Madrid, Córdoba, and Granada on this eight-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.