Toledo: 6 Incredible Sights in the Imperial City

Dramatically rising on a hill above the Tagus River, the historic walled city of Toledo is a magnificent picture that brings visitors back to bygone eras right at first sight. Toledo was the imperial capital and main seat of Charles V, Holy Roman Emperor, and thus a prominent centre of art, culture and commerce in Europe for years until Philip II, Charles’s son, moved the Spanish court to Madrid. Puerta de Bisagra, Toledo’s famous city gate and the main entrance to the city, bears a huge rendition of the emperor’s coat of arms.

Because of its extensive cultural heritage, Toledo was listed as UNESCO World Heritage Site in 1986.

It wasn’t only Charles V and Christians who had a hand in Toledo’s rich history though. Muslim and Jewish communities shaped Toledo as well, making it also known as the “City of Three Cultures” and bestowing impressive architectural landmarks that have become synonymous with the city today. Just look at the arched mosques, Gothic cathedrals and Sephardic synagogues crammed into its historical core and you’ll realize that Toledo’s unique tri-culture heritage weaves the very fabric of everyday life in the city.

There are tons of amazing things to see and do when you visit Toledo, and you better get your trusty shoes ready as it is a city best explored on foot. From steep streets and cobblestone lanes to age-old castles and delicious food and drinks, Toledo is a delight that will keep you coming back. Check out our top picks of must-visit sights and start planning your trip!

1. LA PUERTA DE BISAGRA

Toledo’s massive gate remains an intimidating sentinel despite the centuries. Officially known as La Puerta de Bisagra Nueva (The New Bisagra Gate) to distinguish it from La Puerta Bisagra Antigua constructed in the 10th century, the imposing northern city gate is one of the most arresting things anyone visiting Toledo could lay eyes on. Two semi-circular stone towers flank its triumphal arch on which Carlos V’s and the city’s imperial double-headed eagle is emblazoned. It superseded the Bisagra Antigua as the principal entrance to the city after its construction in 1559, and was meant to display the tremendous might and reach of the Emperor at the height of Spain’s power.

2. CATEDRAL DE TOLEDO

Toledo’s illustrious cathedral is a medieval Gothic masterpiece that continually ranks among the top cathedrals in Spain. Its exterior alone will take your breath away but wait until you get inside where rose windows, ribbed vaults, pointed arches, and flying buttresses create a beautifully sublime atmosphere. Don’t forget to feast your eyes on the cathedral’s sacristy—it’s actually an art gallery filled with works by old masters including Goya, Velázquez and of course, El Greco. As for the stunning stained-glass pieces, the oldest is the rose window placed above the Puerta del Reloj. There’s also the elaborate frescoes and Gothic tombs featured in the 14th century Capilla de San Blas, and the 500-year old wooden Mudéjar ceiling in the chapter house.

Tip: If you want sweeping views of Toledo’s historic centre, an extra €3 gains you entry to the cloister’s upper level and the bell tower.

3. THE ALCÁZAR

Out of the all things to see in Toledo, the Alcázar is the one you literally cannot miss. It’s perched on the highest part of the city, dominating Toledo’s skyline. What’s with the location, you ask? The Alcázar was originally a fortress erected in the 10th century to strategically overlook the eastern plains of Castile, at a time when Toledo was the most significant city in all of central Moorish Spain. It was later transformed to function as a royal residence but became an army academy instead when the capital was moved to Madrid. The Spanish Civil War almost destroyed the Alcázar in a 70-day siege of the garrison in 1936, then Franco rebuilt it to be the vast military museum we know today. Uniforms and medals are displayed inside, but what you should not miss is the recreation of Moscardo’s bullet-wrecked office, considered as the Alcazár’s most macabre sight.

4. MONASTERIO DE SAN JUAN DE LOS REYES

When Isabel and Fernando, the Catholic King and Queen (1477-1504), celebrated the victory at the Battle of Toro and the birth of Prince John, it seems like they wanted to make sure no one would doubt their eternal gratitude and nothing seals the deal like a huge, beautiful monastery. The 15th century Monasterio is a flamboyant Gothic marvel which features an astounding two-level cloister and exquisite Mudejar architecture. Vaulting pinnacles, superb statuary and detailed gargoyles mark the structure, and the adjacent church is brimming with the Catholic monarchs’ coat of arms. Isabel and Fernando originally planned to be buried in the stunning monastery but eventually chose to rest instead in Granada, their most prized conquest. See those chains hanging from the northeastern façade? Those belonged to the Christian prisoners freed from Muslim Granada.

5. PUENTE DE SAN MARTÍN

Crossing this medieval bridge over the Tajo River is a big must-do not only because it is one of Toledo’s foremost symbols, but also for the spectacular panorama of the old town it offers. Historically speaking, it was built in the 14th century and its defensive towers on either side remain intact. Take note of the statue of a woman in the middle arch. It is believed to depict the wife of the architect in charge of bridge’s construction.

6. MUSEO DEL GRECO

No visit to Toledo is complete without dropping by the El Greco Museum, particularly for art lovers. Born in 1541 Domenikos Theotokopoulos in Crete, El Greco (the Greek) was one of the most influential and important Spanish artists of all time. The Burial of the Count of Orgaz (1586) and The Agony in the Garden of Gethsemane (1590) are two examples of his incredibly moving pieces. The El Greco museum, which consists of a 16th century house and an early 20th century building, opened its doors to the public in 1911 and underwent a recent renovation to better showcase its impressive collection. Aside from El Greco masterpieces, the museum also houses 17th century pottery and furniture from Talavera de la Reina and paintings by other Spanish artists.