Monastery of St. John

This masterpiece of Isabelline Gothic was built by King Ferdinand II and Queen Isabella I to celebrate the birth of their son, Prince John.

As with so many buildings in Toledo, the Monasterio de San Juan de los Reyes bears witness to a whirlwind of cultural influences. Completed in 1504, the building is an example of what is called Isabelline Gothic: the architectural style of the Crown of Castile, this is a transitionary stage between late Gothic and early Renaissance modes, with original features and decorative ideas taken from Mudéjar and Flemish architecture.

Its full name in Spanish means ‘Monastery of St. John of the Kings.’ King Ferdinand II and Queen Isabella I built it to celebrate the birth of their son Prince John - as well as their victory over Portuguese forces at the Battle of Toro - and it was also dedicated to St. John the Evangelist, for use by Franciscan friars. The monarchs also initially intended it to be their mausoleum, but later changed their minds and were buried in Granada.


Among the monastery’s highlights are the larchwood Mudéjar ceilings in its upper cloisters, which stand in contrast to the German cross vaults of the ground floor. Intricately carved and painted, they feature the monarchs’ motifs and coats of arms and the motto Tanto monta, monta tanto (‘As much as the one is worth, so too is the other’) - a vow that the two didn’t really stick to in their marriage, but apt testament to the building’s mixture of architectural influences. The cloister also features a delightful garden and courtyard, surrounded by a menagerie of stone gargoyles.

The north-facing granite exterior features the unusual decorative feature of rows of iron shackles and manacles, ordered there by the Queen in 1494: they were removed from prisoners freed from the Moors after the long Granada campaign, and remain as a symbol of Christian triumph over adversity. Badly damaged during the Napoleonic occupation of Toledo, the monastery underwent a long period of restoration between 1883 and 1967. Today it remains a high point in the fascinating world of Toledan architecture.

Nearby Attractions

See all attractions in Madrid
Toledo
An incredible medieval city that showcases the creative clash of Arab, Jewish and Christian culture.
Cathedral of Toledo
This 13th century cathedral is perhaps the paramount example of Gothic architecture.
Church of St Tomé
A medieval church that is home to a world-renowned work by El Greco.
The Burial of the Count of Orgaz
El Greco’s most famous masterpiece, still displayed in its original setting.
Synagogue of El Tránsito
A magnificent 14th century Toledan synagogue, famed for its intricate stucco decoration.
Synagogue Santa María la Blanca
Constructed in 1180, it is one of the oldest synagogues still standing in Europe and a prime example of Mudéjar architecture.

Related Tours

Visit the Historic City of Toledo: Private Day Trip from Madrid

Escape Madrid's bustling streets and embark on a private day trip to the historic city of Toledo, a UNESCO World Heritage site, considered a remarkable city museum, with a rich heritage deeply shaped by the Jews, Muslims, and Christians who once lived there, practising their faiths and working together in harmony. This immersive experience of Toledo will not only show you the city’s most iconic landmarks, but also its hidden treasures waiting to be discovered.

On your private day trip, you will:

  • Enjoy a scenic drive to Toledo, and make a quick stop at a panoramic lookout for splendid views of the city;
  • Admire the city’s unique position, encircled by the Tagus River, and learn how this offered a natural defence that has contributed to its storied history as a fortified town;
  • Step into the Town Hall Square and see the grandeur of Toledo’s architecture flanked by historic buildings, including the Town Hall, a beautiful Renaissance structure, and the Archbishop’s Palace;
  • Visit the Primatial Cathedral of Saint Mary of Toledo, an architectural marvel built over three centuries since 1226 and a symbol of the city's role as the spiritual heart of Spain during the Middle Ages;
  • Uncover the details of this Gothic masterpiece with an intricate façade, an elaborate altarpiece, towering columns;
  • Marvel at the cathedral’s stunning collection of artwork, which includes iconic works by El Greco and Goya;
  • Venture into the old Jewish Quarter and walk through a labyrinth of narrow, winding streets once home to a thriving Jewish community;
  • Enter the Church of Santo Tomé and discover one of Toledo’s most famous works of art El Greco’s 'The Burial of the Count of Orgaz' a treasure of Renaissance painting;
  • See the Synagogue of Santa María la Blanca, a rare and precious remnant of Toledo’s diverse cultural heritage with an exquisite mix of Mudéjar, Islamic, Christian and Jewish architecture;
  • Step inside the Hermitage of Cristo de la Luz, a 10th-century mosque transformed into a Christian church and hear the legendary story of the miraculous crucifix that inspired its name;
  • Explore the Monastery of San Juan de los Reyes, one of the city’s most beloved landmarks built in the late 15th century to commemorate their victory at the Battle of Toro;
  • Discover the fascinating Toledo Sheds, and hear all about these historic covered passageways that connect buildings over the streets;
  • Visit a traditional Damasquinado Factory and witness the meticulous art of damascening where gold and silver threads are inlaid into steel to create intricate designs.

Join us on this fascinating private day trip from Madrid to the stunning walled city of Toledo, a UNESCO World Heritage site often referred to as the "City of Three Cultures". Through the centuries, Toledo has been shaped by the coexistence of Christian, Muslim, and Jewish communities which influenced its architecture, religious monuments, and art making the city a living museum. 

Your tour starts from your central accommodation in Madrid as you embark on a scenic drive through the Spanish countryside towards Toledo. Strategically located atop a hill and surrounded by the meandering Tagus River, Toledo’s fortified walls offer spectacular panoramic views of the surrounding landscapes. The city’s labyrinth of narrow, cobbled streets transports visitors back in time with a history that stretches back to the Roman era. The city's prominence truly emerged during the Visigothic period when it served as the capital of Spain. Under Muslim rule, it flourished as a vital centre of knowledge, art, and trade and after its reconquest by the Christians in 1085, Toledo became a cornerstone of Spanish power, playing a crucial role in shaping the nation. 

You will visit the Primatial Cathedral of Saint Mary, also known as the Toledo Cathedral, constructed between the 13th and 15th centuries, this gothic Cathedral is a masterpiece of religious architecture. Your guide will explain the history of the cathedral constructed on top of the site of a former mosque, itself built atop a Visigothic church, symbolizing the complex and layered history of Toledo. The 92-meter-tall Bell tower is one of its most recognizable features, crowned with a spire and decorated with intricate stonework housing the Great Bell of Toledo one of the largest in Spain. It also treasures an impressive collection of art, including works by El Greco, one of Spain’s most celebrated painters. The Sacristy is home to his famous painting, The Disrobing of Christ (El Expolio), as well as other masterpieces by artists such as Goya, Titian, and Velázquez.

Continue to see the city's monumental Alcázar of Toledo, an imposing fortress that now houses an army museum as a testament to Toledo's military significance throughout history. Then you will discover another architectural jewel, the Monastery of San Juan de los Reyes, commissioned by the Catholic Monarchs Ferdinand and Isabella. The monastery commemorates the monarchs' victory over the Moors, highlighting Toledo’s important role in the Reconquista. 

After a well-deserved lunch break (lunch not included) you will make your way through the Jewish Quarter to see the Synagogue of Santa María la Blanca, once a Jewish house of worship and one of the oldest surviving synagogues in Europe. You will enter the Church of Santo Tomé where art lovers will be captivated by the works of El Greco, Toledo’s most famous resident, whose unique artistic style left an indelible mark on the city. His masterpiece, The Burial of the Count of Orgaz, is housed here.

The city is also celebrated for its artisanal craftsmanship, particularly the intricate Damasquinado, a traditional art form where gold and silver are inlaid into steel to create stunning designs. On your last stop, you will visit a specialized factory to delve into the details of this world-renowned fine metalwork, a craft which has been passed down through generations. It’s a beautiful and lasting reminder of Toledo’s artisanal heritage and makes for the perfect souvenir to commemorate your day. 

Finally, relax on your scenic way back to Madrid where your driver guide will drop you off at your hotel or any other central location of your choice.

x

Guides

Join the fastest growing community of professional tour guides.

Partners

Use our easy to integrate toolset to include Tours & Attractions in your customer journey.