Madrid + Toledo

Four years ago, Anthony and I went to Europe for three weeks, and our last twenty-four hours happened to be a layover in Madrid. Because we were young and cheap and curious about Spain’s notoriety for staying out late, we sacrificed a hotel room and spent those twenty-four hours roaming the city. We hung out at Puerta del Sol, we saw a major accident occur (a truck backed into an awning that fell on top of a woman dining outdoors, severely injuring her), we ate jamón and spent an embarrassing amount of time eating churros at Chocolatería San Ginés, and we napped in Retiro Park. It was an odd experience, and I felt pretty ambivalent about Madrid. Since that was my only experience with Spain, I also had no real desire to return to Spain — until a couple of months ago when I found round-trip flights to Madrid for an astonishingly low price of $261.

Madrid’s sleek airport
Most of our trip was spent in Andalucía, but we did spend a couple of days in Madrid, as well as a day-trip to Toledo. Turns out, I still don’t love Madrid, but at least I finally appreciated how livable this vibrant metropolis is.


We stayed at an Airbnb in the trendy neighborhood of Malasaña, which I’d highly recommend. It’s connected to everywhere by metro, walkable to all the touristy sights, and filled with award-winning restaurants, colorful street art, and vibrant plazas swarming with madrileños (locals).

View of Madrid rooftops from our Airbnb living room

We spent our first morning doing the touristy Gran Vía stroll, starting at the elegant Palacio de Cibeles, which was once a post office, and ending at Plaza de España. It’s basically the Fifth Avenue of Madrid, with interchangeable chain stores and foreign tourists moving slowly, but it’s interesting to see the phases of architecture along Gran Vía, from Beaux-Arts to Art Deco. One of the more interesting stores to drop into is an H&M housed in a former theater.

Palacio de Cibeles
The Metropolis Building was designed by a couple of French brothers. The dome is topped by a statue of the winged goddess Victoria, which replaced the original bronze statue of Phoenix and Ganymedes when a rival insurance company purchased the building and the original owners took the statue with them.
Art Deco
The rest of Madrid felt so comfortable, like any other cosmopolitan European city, that we sometimes forgot which city we were in.

Revisiting Mercado San Miguel, which we visited last time we were in Madrid
One of the unique things about Madrid is that you can find Mudejar arches scattered here and there
We loved seeing these same-sex traffic lights, put up during Pride and never taken down

Most of our diet in Madrid consisted of churros con chocolate, as we went to Chocolatería San Ginés pretty much after every meal. It’s an impressive place, open 24 hours yet retaining a classy feel. Servers run around balancing elegant mugs of thick chocolate and little plates of churros.

Churros con chocolate
Apparently we were missing southern Spain already because our favorite meal was at Torre del Oro Bar Andalú, which is an Andalucian tapas bar just off Plaza Mayor. The gory photos of bullfighting filling every crevice of the restaurant is a bit corny, but the food is authentic and even served Granada style (a free tapa with every drink!), with a stream of regulars — perhaps Andalucian transplants? — throughout the afternoon.

Since it was August, a lot of the restaurants I wanted to try were closed for vacation, so one night we reluctantly went to La Barraca, a historic paella restaurant. It reminded me of Delmonico’s, a New York institution with white tablecloths and awkwardly stuffy service. However, we couldn’t deny that the paellas were very good. The next morning we cooked our leftovers for breakfast, and we couldn’t have been happier.

Best paella on our trip
Afternoon Trip to Toledo

Just a half-hour train ride from Madrid is the wonderfully preserved medieval town of Toledo. Once the capital of Spain, it felt like a mix of Rothenburg ob der Tauber in Germany and Dubrovnik in Croatia, some other favorite Medieval towns of mine. Toledo sits high up on a circular rocky hill protected on three sides by the Tajo River, like a moat. It has 2,500 years of tangled history between the Romans, Jews, Visigoths, Moors, and Christians. The city reached its peak in the 1500s, when Spain was in its Golden Age. Emperor Charles V made it his “Imperial City,” and El Greco made his home here. Cervantes’ wife came from near Toledo, and he often wrote about it. In 1561, Philip II moved the capital to a small town north of here called Madrid, beginning the slow decline of Toledo. The whole city is a UNESCO World Heritage site, remaining largely intact despite numerous violent takeovers throughout history due to the fact that it was considered the holiest city in Spain. Its ornate cathedral is one of the most impressive structures in Spain, taking over 250 years to build.

Old winding roads of Toledo
Cervantes is beloved here
Perched up on a hill, overlooking La Mancha
Mudejar touches everywhere
The impressive train station sits below the town center, so we caught a city bus into town. You can  catch #5, #11, #61, or #62 to Plaza de Zocodover. One thing we love about Spain is that buses give out change.

Sunset views from Toledo
Mudejar style train station
Spain claims that marzipan (“mazapán” in Spanish) was invented in Toledo by nuns of the Convent of San Clemente during a famine. There was no wheat but plenty of sugar and almonds, so nuns created a paste out of these ingredients and fed the undernourished people. Mazapán de Toledo is protected by D.O., which means it must be made in the province of Toledo and be at least 50% almonds. We tried mazapán from Santo Tomé and El Café de las Monjas, and both were much better than any marzipan I’ve had in the U.S. Each one is lovingly shaped by hand, and a box of assorted mazapán is the perfect gift.

Besides mazapán, swords are another popular souvenir in Toledo, as Toledo was famous for making the very best steel during the Middle Ages. Knights considered having a Toledo-cast sword to be the highest status symbol.

Unlike on the rest of our trip, Toledo doesn’t have a thriving tapas scene. Instead, Toledo excels at game, which is hunted in the hills to the south. Typical dishes include partridge, venison, wild boar, roast suckling pig, and baby lamb. We had a lovely dinner on the outdoor terrace of Restaurante Placido.

Roasted baby lamb
Tips for future travelers:

  1. It’s simple enough to get from the airport into Madrid by subway, but if you have a lot of luggage or don’t want to transfer, you can also take the comfortable Exprés Aeropuerto to Atocha train station, and then getting a cab. This yellow bus departs every 15 minutes, runs 24 hours a day, and takes about 40 minutes to reach Atocha.
  2. For our few days in Madrid, buying a 10-pack of Metro tickets was perfect for us. We first had to buy a cheap refillable card, and then we were able to share the ten rides. Madrid’s Metro system is fantastic and reminded us of Paris. Lines are color-coded and numbered. You can just tap your Metro card to the yellow pad to open the turnstile — no need to take it out again to exit.
  3. The best itinerary for Toledo is to take a late afternoon train there, so you can see things just as the daytrippers are leaving for the day, and watch the sunset. Then leave the following morning, after exploring a few of the sights that had been closed when you arrived the previous day.
  4. Buy your train tickets to and from Toledo in advance, as they often sell out to commuters. (Since Toledo is so close to Madrid, it makes sense that some people live in Toledo and work in Madrid.)
  5. When on Gran Vía, take a break and head up to Gourmet Experiences (a food court in El Corte Inglés) for a spectacular view of the Schweppes Building.



What’s the best way to end an epic vacation? Plan a layover in a city that you’re pretty ambivalent about before going home. Thanks to our 23-hour overnight layover in Madrid, I wasn’t as depressed returning to the U.S. as I had been when leaving Positano and Milan earlier. I tend to get emotionally attached to certain places, so I look for ways to protect my heart.

Anthony and I didn’t want to waste our layover at a hotel, so our plan was to roam around the city and hop into different places throughout the night. Coincidentally, Spaniards are known for staying out late, so Madrid was an ideal place for this all-night venture.

We started in one of the most touristy parts of Madrid, Puerta del Sol, which means “Gate of the Sun”.  It was originally one of the gates in a huge wall that surrounded Madrid in the 15th century. When we arrived, there was a mariachi band playing in front of an imposing statue, which at first made perfect sense, like finding a hula dancer performing in the middle of Waikiki. But then we remembered — hey, wait a minute, mariachi is from Mexico! Wrong continent, guys.

The area reminded me of Rome, with old buildings, cobblestone roads, and perfect uplighting. We stumbled into a tapas bar called La Antoñita and were led all the way back into a courtyard perfect for intimate meals. We ordered some charcuterie and a glass of rioja. Holy smokes, Spain, I finally get it. I understand now why Spanish ham has such hype. Our plate of charcuterie included jamón ibérico, which melted in our mouths and was nothing like those sad cold cuts you buy in American grocery stores. Jamón ibérico is made from black Iberian pigs in Spain and Portugal. After the fattened pigs follow a strict diet of barley, maize, olive, and acorns, the ham is salted and dried for two weeks, dried for another four to six weeks, then cured for at least twelve months. I would travel to Spain again just to eat more ham.

Jamón ibérico
Jamón ibérico

After wandering around the city and passing through the famous Plaza Mayor, we decided it was time for dessert and headed to Chocolatería San Ginés. This famous café has been serving chocolate con churros (hot chocolate and churros) since 1894. It didn’t close until 7 am, making it the perfect place to hang out overnight. The interior felt like an upscale diner, with lots of mirrors, wood paneling, green velvet seats, and marble tables. The thick, strong, dark hot chocolate was served in a mug, and the churros were light and crispy. We must have sat there for hours, slowly eating our churros and noticing the waves of crowds trickling in throughout the night. The workers were so kind, always giving us free water and never questioning our stay. During our time there, Anthony taught me how to play Griddlers, a picture logic puzzle that he had been playing on subway rides back home. I ended up becoming quite addicted to Griddlers. He later told me that this moment was one of his favorites on our entire trip.

Chocolate con churros
Chocolate con churros

Eventually, we were too tired to even sit still, so we left Chocolatería San Ginés and continued our journey. It was extremely late by then — especially for us, as we’re usually in bed by 11 every night — and roaming around in a foreign but somehow familiar city felt surreal. As we were walking, we heard a huge truck racing down the street. It hastily swerved past us, and just as Anthony turned his head to glare at the driver, the truck stopped and started backing up slowly, straight into a huge awning. The truck knocked off the entire awning, which landed right on top of a woman sitting at an outdoor restaurant. Glass was shattered, and the woman was completely bent forward onto the table. She remained motionless as we cautiously walked toward her. Surprisingly, the woman eventually stood up and looked shocked more than anything else. It was a terrifying incident to witness, but as more and more people arrived to help her, we knew we could be of no use — especially with our level of Spanish — and left the scene. Surreal, right?

We made our way to Retiro Park, one of the largest parks in Madrid. It once belonged to the Spanish Monarchy but became a public park in the late 19th century. The night was windy, so we had to huddle together for warmth. By the crack of dawn, dozens of joggers were out and about, and we noticed how fancy the neighboring area is.

Streets in Madrid have signs with graphics on the buildings. This is the dancing street, obviously.
Streets in Madrid have signs with graphics on the buildings. This is the dancing street, obviously.

In the daytime, the city felt different. Last night, we had been surrounded by shady study abroad students and late-night locals. Now we passed tourists and office workers starting their day. We spent the rest of our time in Madrid eating and sightseeing, napping in front of an opera house, and walking through palace gardens. We had more amazing jamón ibérico for breakfast at a cheap cafe, and then shared paella and tapas at a food market that felt just like Brooklyn. We missed Rick Steves, whose guide books had been so useful in Italy and Paris. I hadn’t bothered to buy a guide book for Madrid since we had less than a day here, but I regretted that decision, as we could sense the lack of commentary as we meandered through town.

Honey mustard bacalao, garlic pepper octopus, and bacalao with tomato and vegetables
Honey mustard bacalao, garlic pepper octopus, and bacalao with tomato and vegetables

By the time we had to return to the airport, I was emotionally ready to go home. Madrid had been more fun than I expected, but, at the same time, felt bizarre. It had put enough distance between Italy and New York, and now my heart was sufficiently protected.

My first day back in New York was beautiful, with clear blue skies, 80-degree weather, and little humidity. It was as if New York knew it had to impress me. When I left my apartment to go to work, I was faced with film trailers parked all along our street. In New York, you get used to your street being used for films, but, after being in awe of so many places the past few weeks, it was a nice reminder that other people are actually in awe of your home. The ease with which I was able to refill my Metrocard was much appreciated after struggling with other cities’ transit systems. And once I got onto the train, I relished the blast of air-conditioning that filled each car. I got off at my stop near Columbus Circle and was overwhelmed by how attractive this area is. As I walked to work, I noticed some European tourists and was excited for them. Glad to be back, New York!

Traveling is even better when you know you're coming home to the best city in the world
Traveling is even better when you know you’re coming home to the best city in the world

Tips for future travelers:

  1. If you’re like me and get emotionally attached to places, plan to have a long layover in a city that doesn’t intrigue you. In fact, make it a challenging layover like ours. Instead of getting a hotel room, we roamed around all night, so we were looking forward to a bed — any bed, even a bed back in America.
  2. Layovers are a great way to explore a city that you wouldn’t necessarily want to visit for its own sake. As long as you have at least five hours, I would definitely recommend leaving your luggage at the airport and finding the quickest way into town.
  3. You can control how long your layover is with a little trick that I learned while planning for my next international trip: I needed to fly from Manila to New York but noticed that most of the cheap flights had layovers in Seoul, a city that I would love to visit. Unfortunately, the layovers were just a few hours long. Since I wanted at least a few days in Seoul, I changed my search to a multi-city search: Manila to Seoul, and Seoul to New York two days later. For the same price of a flight from Manila to New York, I can now have my two-day layover in Seoul.
  4. If you want to avoid paying for a hotel on an overnight layover like we did, do a little research first. Make sure you’ll be in a city that is safe at night. We lucked out because Madrid is alive practically all night. Then, have some late-night places in mind that can be hangouts when you’re too tired to roam around. We didn’t just stumble into Chocolatería San Ginés; I had found it online and knew that it would be open all night and was a good place to hang out.