This City in Spain Is Like 'Don Quixote' Meets 'The Wizard of Oz'
The medieval city is a labyrinth of lore… and Michelin-star eats.
If you’ve been to Madrid or read Don Quixote, you’ve most likely heard of Toledo: a walled, medieval city that looks like a real-life version of the Emerald City from The Wizard of Oz. Trains and public transportation frequent the ancient city multiple times of day, as it's a quick 45 miles south of Spain’s capital, making it an easy day trip for the majority of travelers. And if you spend the day with Adolfo Ferrero Martinez, a Toledo native and owner of the guide company Toledo de la Mano, you’ll want to cancel your return and stay for a night or century or two.
Once the capital of Spain (until 1560 when Philip II decided to move his court to Madrid), it's easy to see why the king deemed Toledo worthy of the royals. The town is set on a hill surrounded by the Tagus river and Castilla-La Mancha plains, and a labyrinth of winding roads lead upwards to a castle perched at the top. “As the most important city in Spain until the 16th century,” says Martinez, “there is no place in the country where you could better trace its culture, its art, and its traditions than in Toledo—a place frozen in time."
Declared a UNESCO World Heritage Site in 1986, Toledo is consistently photographed as one of the prettiest places in Spain, so we’re throwing you a few more reasons to stay overnight—including a two-Michelin-starred restaurant in a cigarral, seeing the city lit up at night, eating marzipan in its birthplace, exploring the melting pot of cultures, and seeing why the painter El Greco fell in love with this place.
Explore the melting pot of cultures
Known as the “city of three cultures,” Toledo’s architecture is where it's at thanks to the Christians, Jews, and Muslims that co-existed together here throughout history. And it’s a super walkable city to see it all.
Martinez’s custom, bespoke tours will take you around the city and highlight what’s special about it. It’s worth noting Martinez wrote his own guidebook as the rest of the information on the market was lacking. He specializes in focusing on what you’re actually interested in, and IMO is one of the greatest tour guides around.
Some of the buildings you might see on one of his tours encapsulate the three cultures. The striking Mosque of Cristo de la Luz is the only mosque still standing—and one of the most important pieces of Hispanic-Muslim and Mudejar architecture in all of Spain. The Cathedral of Toledo is one of three 13th-century High Gothic architecture and, as Martinez notes, there is no other monument in the city that better represents the power of the Catholic Church and its expression via art. The Synagogue of El Tránsito serves as a prime example of Jewish power in medieval Toledo—and for architecture buffs, true Mudéjar style.
Eat two-Michelin-star-awarded food in a mansion
Those who overlook smaller cities for gastronomic experiences are missing out, and Toledo is no exception. Restaurante Iván Cerdeño is a two-Michelin-starred restaurant situated in a beautiful cigarral (a historic country mansion) with unmatched views, helmed by chef Iván Cerdeño.
Admire the rose garden and grounds on the way up to the restaurant. Inside, experience a taste of La Mancha cuisine by way of traditional dishes and local ingredients, based on what’s in season. Expect chef’s interpretations of dishes like asadillo Manchego (roasted peppers and tomatoes, garlic, cumin, and olive oil), sardines and red partridge, and perfectly executed wild game meats. Splurge on the “forgotten menu” (seven courses) or the “memory of a cigarral '' (10 courses) with local wine pairings for a memorable souvenir.
Wander the labyrinth
Walk over the Puente de San Martín, a medieval bridge that crosses the Tagus river, and adventure in the city's labyrinth. The cobblestone streets wind around the old town, where the mosques, synagogues, and Gothic churches collide. The high-walled streets also keep you cool on a hot summer day.
Many of the shops in the old town cater to tourists, but they’re a prime opportunity to shop for damask and steel. Keep an eye out for little figurines of Don Quixote on his trusted donkey or perhaps attacking windmills, since the fictional character by Miguel de Cervantes is from this region in La Mancha and the beginning of the book takes place here. There’s also a statue on the street of Cervantes himself.
Also, it’s worth sticking around till night, since seeing the cobblestone streets in the evening with the town lit up is a completely different and romantic vibe than during the day.
Eat marzipan, Manchego cheese, and dishes favored by Salvador Dalí
Marzipan was invented in Toledo by the nuns of the Convent of San Clemente in the 11th century. When the nuns once ran out of wheat resources for bread, they mixed sugar and almonds together instead, and bam—created the insanely sweet and delicious confectionery. There are countless marzipan spots around the city, but only three places make it the traditional way. Santo Tomé, a 7th-generation family business, is the only place that does the entire production—from start to finish—in the city. Don't forget to grab a few boxes of marzipan to take back home (heck, even your gluten-free friends can enjoy this treat).
For a few local restaurants inside the walled city, Martinez is a fan of La Orza, Alfileritos 24, and El Botero (where the dumplings are some of the most succulent and savory ones I've ever had). For restaurants with views, you'll have to cross the river. Aside from the parador and Iván Cerdeño, check out Venta de Aires, an iconic restaurant from 1891, serving traditional fare like red partridge. Art enthusiasts will be stoked to know they're dining in the same spot where surrealist Salvador Dalí used to get drunk and run through the town in costume.
And since you're in Manchego cheese country, it's only fitting to hit the Museo del Queso Manchego to learn the backstory of the cheese, plus other traditional dishes of the area.
See Toledo as El Greco did
ICYMI, Domḗnikos Theotokópoulos, the Greek painter and sculptor best known as El Greco to the mainstream, helped define and influence the Spanish Renaissance. El Greco first tried his luck in Madrid, but it was a no-go, so he found himself in Toledo. There he received commissions for some of his most famous pieces, including “View of Toledo” (one of the only two surviving landscape paintings from his works) and “Opening of the Fifth Seal.”
Check out a sizable collection of El Greco pieces and other 16th century art in the Museum of Santa Cruz, housed in a previous orphanage and hospital. And of course stop by Museo del Greco, a museum dedicated to his works. In case you haven't seen the “View of Toledo” inspiration IRL, make your way to the Parador de Toledo at sunset to instantly understand why he painted it in the first place.
Check into a cigarral, a parador, or stay in a hotel inside the labyrinth
There are several standout hotels in Toledo. Paradores are state-run hotels in Spain, consisting of properties housed in monasteries, castles, fortresses, and covenants, or exceptional modern spots like Parador de Toledo. People make their way to this hotel to capture the best panoramic view of Toledo. If you overnight it, enjoy posting up on the "Hill of the Emperor” at sunrise for one of the most awestruck views with an espresso in hand. There’s also a posh pool for summer days when the afternoons are best spent cooling off as the town takes a siesta.
Check into Cigarral de las Mercedes, a five-hectare estate with stunning views of the city, to see what it’s like to stay in a fancy Spanish mansion for a couple of nights. The garden rooms are situated on an olive grove with an outdoor shower in the private garden, giving the feeling it’s hours away from the city center, when in fact it’s less than two miles.
Stay inside the city walls at Eugenia de Montijo, Autograph Collection to see what happens within the fortified town after dusk. The luxury hotel is tucked away on a narrow cobblestone street, within walking distance from all sites, attractions, and restaurants. The old building is also the former palace of the Empress Eugenia de Montijo of France. At night, if you open your windows, you can almost feel the history of the city come alive in your room.