Toledo Travelers Recommend

Dramatically positioned on a hill above Castilla-La Mancha, Toledo is known as the City of Three Cultures because of its medieval mix of Arab, Jewish, and Christian monuments. Here are a few ways to make the most of one day in the ancient Spanish city.

Morning: Take in the City’s Sights

Many travelers visit Toledo on a day trip from Madrid. Most tour options include transport from the capital, which saves you the stress of booking train or bus tickets separately. Regardless of whether you’re daytripping or staying the night, tours provide a great intro to the city and typically stop at the Alcázar of Toledo, the Jewish Quarter, the Monastery of San Juan de los Reyes, and the Church of Saint Tomé, home to a painting by El Greco, the city’s most famous son. Alternatively, a hop-on hop-off bus tour lets you explore at your own pace.

Afternoon: Sample the Region’s Flavors

Devote the afternoon to the flavors of Montes de Toledo on a wine and food tour of the neighboring region. Tours let you taste wines with a local sommelier and offer insight into growing practices. Along with wine tasting, you'll typically taste foods from the Montes de Toledo region, such as cheese, olive oil, venison, and wild boar.

For more culinary delights, head to Plaza de Zocodover, where you’ll find a cluster of tapas bars and restaurants housed in historic buildings.

Night: Delve Deeper

There are several options for exploring Toledo by night. History buffs can learn more about the Knights of Templar on an evening walking tour of places associated with the mysterious medieval order; guides point out hidden symbols scattered around the city and tell tales about the noble warriors. These tours typically finish with a dinner prepared using gourmet products from the Castilla-La Mancha region.

Another option for oenophiles is more wine: evening wine shows tend to include a virtual tour of the region’s wineries, tastings of different varietals, and traditional Spanish tapas.

Most travelers visit the ancient Spanish capital of Toledo on a day trip from Madrid. However, this UNESCO World Heritage-listed city—which is replete with medieval Arab, Jewish, and Christian monuments—deserves more of your time. Here’s how to spend 48 hours in Toledo.

Day 1: Unpeel Toledo’s Layers of History

**Morning:**Get your bearings on a private or group sightseeing tour of Toledo. Tours typically cover the Alcázar, Jewish Quarter, Monastery of San Juan de los Reyes, and the Church of Saint Tomé, home to a masterpiece by El Greco. For more flexibility, opt for a hop-on hop-off bus tour.

**Afternoon:**Take a closer look at one the city’s most important landmarks—and skip the long line to enter—on a private tour of Toledo Cathedral. Tours typically visit the Primate Temple, Chapel of Kings, cloister, and Chapel of San Blas, and give you ample time to admire masterpieces by El Greco, Tiziano, Velazquez, and Caravaggio. 

**Night:**Dive into the history of the Knights of Templar on an evening walking tour. Guides take visitors to places associated with the secretive religious order and point out hidden symbols along the way. Tours typically finish with a dinner prepared with gourmet products from the surrounding Castilla-La Mancha region.

Day 2: Revel in Local Culture

**Morning:**Kick off your second day by soaring across the sky in a hot-air balloon. Get birds-eye views of the historical center, the River Tajo, and the Alcázar of Toledo while your pilot talks about Toledo’s rich history. Balloon tours typically include a glass of Cava and brunch.

**Afternoon:**Devote the afternoon to attractions you missed yesterday. If you’re interested in Renaissance painter El Greco, admire more of his work at the Museo del Greco or, if the city’s Jewish history is of interest, visit the 14th-century Sinagoga del Tránsitosynagogue, which houses the Museo Sefardí, dedicated to Sephardic culture in Spain.

**Night:**Conclude your visit to Toledo with a taste of its food scene. Options include a wine show with tastings and a virtual tour of the region’s wineries, or a cheese, olive oil, and wine tasting experience focused on foods from the Castilla la Mancha region.

Toledo combines a dramatic hilltop setting with monuments from Christian, Jewish, and Muslim legacies. Add El Greco paintings and excellent regional produce to the mix and you’ve got one of Spain’s must-visit cities. Here’s how to make the most of three days in Toledo.

Day 1: City Sights

A great way to get acquainted with Toledo’s main landmarks is on a sightseeing tour. Group and private tours typically visit the Alcázar of Toledo, the Gothic Toledo Cathedral, the Jewish Quarter, the Monastery of San Juan de los Reyes, and the Church of Saint Tomé, home to a masterpieces by the Spanish Renaissance painter El Greco. Alternatively, a hop-on hop-off bus tour gives you the flexibility to set your own schedule and explore Toledo at your own pace.

In the evening, you can take a night tour that reveals the city’s association with the mysterious Knights of Templar, a medieval religious sect. Afterwards, head for the historic Plaza de Zocodover to take your pick of restaurants and tapas bars.

Day 2: Cultural Immersion

Start your day with a hot-air balloon ride over the city for the best views of the Old Town, River Tajo, and Alcázar. Hot-air balloon tours typically include brunch and a glass of Cava after landing.

Now that you’ve got your bearings, delve deeper into Toledo’s rich cultural heritage on a private tour of Toledo Cathedral, which allows you to skip long entrance lines and benefit from in-depth tours of the Primate Temple, Chapel of Kings, Chapel of San Blas, and masterpieces by El Greco, Velazquez, and Caravaggio. Art lovers can also visit Museo del Greco and Museo del Cruz, an arts and ceramics museum housed in a 16th-century hospital. 

Conclude your day with an introduction to the Castilla la Mancha region’s culinary culture during a cheese, olive oil, and wine tasting experience.

Day 3: Take a Trip

Although many travelers visit Toledo on a day trip from Madrid, the city is a good base from which to explore other parts of the region. Having thoroughly explored Toledo, you could easily spend your third day in another nearby town. Options include Consuegra, known for its windmills and association with the epic Don Quixote; the UNESCO World Heritage Site of Aranjuez, which you can also reach by train; and Chinchón, a charming town famous for its food festivals.

Skip the hassle of driving on a day trip to the historic city of Segovia. There, you can visit attractions such as the Roman-built aqueduct, the 16th-century Cathedral of Segovia, and the Alcázar of Segovia, a UNESCO World Heritage Site. Tours often conclude in Madrid and offer a convenient way to combine return transport with a day of sightseeing.