Toledo, Spain

Toledo, Spain is usually mentioned as everyone’s favorite small city and for good reason. This ancient town contains thousands of years of history from the Jewish quarter to the Moorish buildings to the Christian monarchs. It’s a must-see day trip on any visit to Spain!


Toledo once served as the capital of Spain and was declared a World Heritage Site by UNESCO for its extensive cultural heritage. With its position on a bluff high above the Tajo River, it was a practically impenetrable site perfect for a fortified city.

Toledo was part of the Roman Empire and its Roman circus was one of the largest in Hispania. After the fall of the Roman Empire, Toledo became a capital of the Visigoth kingdom. With leading church bishops in the town, it became the head of the church and monarchy.

In the 8th century, the invading Moors from North Africa overtook the town (and much of what is now Spain), spreading Islam and building mosques. Christians conquered the town in the 11th century, making it the home of the monarchy during Charles V’s reign in the 16th century. Many Spanish royals from past centuries were born here. The city also became known for the artistic talents of one of its residents, El Greco, who moved here in 1577.

The city also had a significant Jewish population that was severely persecuted under both the Christian and Muslim rulers. During Queen Isabella’s time (15th century), the Jewish people were forced to flee, leaving behind beautiful synagogues and artwork. 

During the 20th century Spanish civil war, Toledo was under siege by forces loyal to the Republic when a rebel commander refused to support the government in Madrid and hid in Toledo’s alcázar (castle). After the war, the well-preserved town became mostly known for its tourism with millions flocking to its cobbled streets and quaint alleys.


Toledo is an easy day trip from Madrid. We hired a private tour guide and driver through Letango Tours to meet us at our Madrid hotel and drive us to the city. It was fantastic! You can also take a quick train from Madrid if you want to do a self-guided tour. If you do your own tour, check out the value of a Toledo tourist wristband that can save you money if you enter several of the sites below.

If you have a driver, I highly recommend stopping outside the city for a sweeping view of its fortified walls (follow the Ronda de Toledo signs). It was so beautiful! 

Once in the city, follow Rick Steves’ walking tour (although I recommend reversing its path) to get the most out of your trip – find it in his excellent guide book. It’s a hilly city but small and very walkable. If you have small kids, they’ll love taking the tourist train (meets at Plaza de Zocodover).

We started our tour in the Jewish quarter at the Puerta del Cambron. Walk through its narrow entry and notice the menorah signs on the ground that signify you’re in the Jewish section of town.

King Ferdinand and Queen Isabella issued the Alhambra Decree in 1492 (the same year as they sent Columbus to the new world!). This decree ordered the expulsion of all Jews from their kingdom. Much like they drove out the Muslims, Ferdinand and Isabella wanted Spain to be a Catholic, and Catholic only, country. You’ll see the physical effects of this history in this section of town.

Start your walk at the monastery of San Juan de los Reyes (St. John of the Monarchs), a beautiful Franciscan monastery that was originally built in the 15th century to celebrate the 1476 victory at the battle of Toro, which united Spain. It was supposed to be the burial site of Ferdinand and Isabella; however once the Moors were driven out of Granada in the south of Spain, it became their final resting place. Napoleon’s troops tried to destroy the monastery during his occupation of Toledo in 1809, but it survived. Buy your ticket at the entrance (€3 or wristband) and walk into this quiet, reverential site. Your first stop is the cloister, which is a nice place to rest.

The chapel is small but beautiful. See if your kids can spot all of the “Fs” and “Ys” engraved in the stone (for Ferdinand and Ysabel). 

Go upstairs to get a bird’s eye view of the cloisters.

And be sure to look up at the magnificent ceilings!

Don’t miss the chance to enter the chapel from above.

You’ll exit out of the monastery through the former sacristy where you’ll find a skeleton reminding you of our mortality.

Continue walking through the Jewish quarter to the Santa María la Blanca, a synagogue-turned church in a Moorish style. Built in 1200 and turned into a church in 1391, it’s reported to be the oldest synagogue still standing in Europe! Buy your ticket (€4 or wristband) at the gift shop off the courtyard and then enter the startlingly beautiful, empty building. To me, it was one of the most special places we saw in Toledo, marrying Jewish, Islamic, and Christian cultures in one building. It’s so pretty, it’s hard to imagine Napoleon’s troops using it as a stable! 

If you want to visit a current synagogue, go to the nearby 14th century Tránsito Synagogue and Sephardic Jewish Museum. Art enthusiasts will want to detour past the synagogue to the El Greco Museum

Wind your way through the twisting streets to leave the Jewish quarter, and walk by the shops lining Calle de Santo Tomé.

Be sure to stop in the Confitería Santo Tomé to see the largest statue made of Toledo’s specialty, mazapán. It’s an almond sugar dessert that is famous in Toledo, and this store is a great place to get a special treat or souvenir!

Another great souvenir area can be found just past the Santo Tomé Church (enter to see a famous El Greco painting). Toledo is known for its metal-working, including swords and jewelry. We watched this artisan in action and then went inside the beautiful shop. The delicate gold overlay (called damascene) is really spectacular!

As you walk down Calle de Santa Úrsela, keep your eyes open on the left for an alley that gives you a peek of the amazing Toledo Cathedral. It’s a great spot for a family photo!

Head towards the Toledo Cathedral, one of the grandest in Spain. Buy your tickets just across the street from the entrance on Calle Cardenal Cisneros (€10 and includes audio guide) and enter this beautiful space. 

Walk down the nave and see the ornate choir with its gilded wood altarpiece.

Head towards the front right (as you’re looking at the doors) to enter the treasury where a 10-foot high ceremonial tower is displayed. This monstrance is for the Holy Communion wafer that is paraded through the city during the festival of Corpus Christi. What’s really cool about it (other than all of that gold!) is that it’s made of gold and jewels brought back by Columbus from the new world.

Go back towards the middle and enter the choir to see statues and amazing carvings.

The seat backs are amazing!

Walk around the choir and then head to the back of the church to see the high altar.

Behind the high altar is the Transparente, an altarpiece with 3D angels and religious figures. It’s really something to see!

Don’t miss the hanging hats that signify a bishop’s tomb underneath your feet.

Enter the sacristy which is now a museum of El Greco paintings.

Don’t forget to look up at the amazing ceiling!

Exit through the cloister and be sure to see the small chapel before leaving.

Leave the cathedral and walk on the Calle del Comercio towards the Alcázar. This street has lots of shops, including more mazapán bakeries! We bought more at Turrones Artesanos.

The road opens up into Toledo’s most well-known square, Plaza de Zocodover. It’s a pretty, open space with lots of restaurants and souvenir shops that hide a sordid history from the Spanish Inquisition. This is a great place to end your tour with a meal at a local restaurant or ice cream from a neighborhood shop. 

History buffs will love to tour the Army Museum at the Alcazár. If you want even more art, you can check out the Santa Cruz Museum. We didn’t have time to visit on this trip, but I’ve got them on my list for next time!

Toledo is a Spanish city that allows you to see the real Spain from hundreds of years ago. From its storied history as a capital that was home to royals to its unique blend of cultures and religions, it’s one of my favorite places we visited in Spain!

Helpful hints:

  • Tour time: We were able to do this walking tour in 3-4 hours. To see even more of the museums and town, take the full day.
  • Dining options: There are many great restaurants in the city. We ate some tapas at a restaurant off Plaza de Zocodover that was recommended by our guide and Rick Steves, El Trébol. Don’t miss tasting the Toledo specialty dessert, mazapán!
  • Nearby hotels: With it being such an easy day trip from Madrid, we didn’t spend the night in Toledo. Check out the suggestions from Rick Steves’ guidebook for more information.

Books to Read:

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