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Toledo in a Day

Updated: Feb 10, 2023

Lovers of food and wine adore the river cruise route from Lisbon to Madrid, perfectly bookending a grand journey through Portugal and Spain. From seaside Sintra to Porto, the gateway to the Douro River Valley, there are wines for days, indulgent meals to savor, and medieval sights at which to marvel.

One of the most captivating towns in the area is the ancient walled city of Toledo, a fantastic day trip when sailing through this region. Just west of cosmopolitan Madrid, the city is set on a hill above the plains of Castilla-La Mancha. Formerly the home of Mannerist painter El Greco (check out his namesake museum and his masterpieces throughout the city’s churches and convents), the town is beloved for its well-preserved Arab, Jewish, and Christian monuments, including the Moorish Bisagra Gate, the Mudejar-style Sol Gate and the lively Plaza de Zocodover in the old quarter.

If you have a day in Toledo, here’s what we’d recommend!

Catedral de Toledo

Marvel at its Gothic architecture, soaring tower, and grand sanctuary within, with 88 ornately decorated columns and impressive stained-glass windows dating from the 14th to 16th centuries. The sacristy holds El Greco’s Disrobing of Christ and series of 16 Apostles, and Goya’s Arrest of Christ.

Casco Historico (Old Town)

Don’t miss this UNESCO World Heritage Site for its labyrinthian pedestrian streets, secret courtyards, and tiny artisan shops. Feel the juxtaposition of three cultures in more than a hundred monuments, palaces, churches, convents, synagogues, and mosques. Scroll through the La Juderia (Jewish Quarter) and visit the Sephardic museum, which is a fine introduction to Jewish Life in Toledo before the Inquisition.

Alcazar de Toledo

Spend a couple of hours at the imposing Moorish fortress looming above the city. Built on the site of an earlier Roman fort, the castle was renovated by Christian kings and is today an impressive square shape with four corner towers (added by Emperor Charles V in the 16th century). Don’t miss the Army Museum, with exhibits about the Spanish Civil War (during which the Alcazar was used as a Nationalist garrison).

Museo de Santa Cruz

Art and history aficionados won’t want to miss this exceptional museum that occupies the former, 16th-century Hospital de Santa Cruz. Admire its Plateresque facade, then move inside to explore the Fine Arts, Decorative Arts, and Archaeology collections. Look for works by El Greco and Luis Tristan - in particular El Greco’s large-scale Assumption of the Virgin. See Flemish tapestries from the 15th and 16th centuries, as well as a huge collection of prehistoric, Roman, Visigothic, Moorish, and Mudegar artifacts and decorative objects.

Want more than a day? We would, too! Toledo is well worth the excursion. Let’s chat about how to make the most of your time there.

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