A Perfect Day in Toledo: Spain’s Timeless Hilltop City

View of Toledo across the Tagus River

I've been to Madrid several times over the past few years, but never found the chance to visit the nearby towns until now. I heard a lot about Toledo, and I knew this day trip was going to feel like stepping back in time. I had the opportunity to visit Segovia in the same trip (see my other post on this city as well), so I was ecstatic to finally cross both of these lovely cities off my bucket list. Just 30 minutes from Madrid by high-speed train, this UNESCO World Heritage city is a cutting-edge destination of Spain’s Christian, Jewish, and Muslim past, with winding medieval streets and historic landmarks. My day trip certainly did not have any dull moments and so today I'm here to have a pointed conversation and share my experience in this timeless hilltop city. (Puns very much intended, more on this in the next paragraph).

History of Toledo

You may ask yourself, why the sword related puns? Toledo had been the heart of Spanish sword-making for over 2,000 years. The city’s reputation began in Roman times, when “Toledo steel” became prized across Europe for its exceptional strength, flexibility, and craftsmanship. It was so renowned that even the Japanese samurais were aware of the Toledo steel by the ways of Spanish merchants and Portuguese Jesuits. As for the city itself, it was founded as a Roman colony in 193 BC. Toledo rose to prominence through the Roman, Visigothic, Moorish, and Castilian eras—evolving from Roman settlement to Visigothic capital, a jewel of Al-Andalus, and later the heart of the Kingdom of Castile.

Getting To Toledo From Madrid

Similar to my other Segovia post, I assume that your starting point is Madrid. To get to Toledo, you first have to go to Madrid's Puerta de Atocha station and catch the morning train. I highly recommend buying your train tickets on Renfe, which is the main Spanish railroad company. As you can see in the above screenshot, the cheapest round trip will cost you €22.20 (~$26USD) round trip. Within 30 minutes, you will find yourself hopping off the train into Toledo's train station, which was a beautiful piece of architecture itself. From there, it’s a quick bus or taxi ride into the old town, though I highly recommend walking if you’re able. Therefore, bring some comfortable shoes as there will be a lot of walking/hiking mentioned in this post. The approach across the river gives you your first postcard-worthy view of the city, framed by stone bridges and centuries-old towers.

First Stop: Scenic Arrival

Before diving into the city streets, I made my way to Puente de Alcántara, the first point of interest you will encounter. On Google Maps, you can search for "Mirador Rio Tajo" once you walk towards the city center from the train station. I walked around for about 15–20 minutes, strolling along the boardwalk and soaking in the view — the bridge perfectly framed in the foreground, with the city center unfolding in the background like a perfect landscape photo. Head down to the riverbank, grab a spot on the rocks, and just take in the mix of bird calls and people’s voices around you. Then, walk across the bridge and through the Puerta de Alcántara, where you will start your journey within the city walls.

Exploring the Greco Museum

16th century house with a courtyard at the Greco Museum

My first stop inside Toledo's ancient walls was the Greco Museum, a museum dedicated entirely to the works of Doménikos Theotokópoulos, better known as El Greco. This 16th-century Greek painter left his mark on the Spanish renaissance, spending the latter half of his life living in Toledo, so his art feels right at home here. Inside, you’ll find some of his most celebrated works, including View of Toledo and The Disrobing of Christ (El Expolio).

The museum closes early at 3 p.m. on Sundays, so I made it my first stop before exploring the rest of town. On other days, it stays open until either 6 p.m. or 7:30 p.m., depending on the season. General admission is usually €3, but on my visit—perhaps thanks to Semana Santa—it was free. Sometimes, timing really is everything.

Wandering the Streets

After soaking in the art, I wandered into the labyrinth of narrow, winding streets that make up the Jewish Quarter. Along the way, I ducked into a few artisan shops, famous for Toledo’s steel swords and bright, hand-painted ceramics. Buying knives wasn’t exactly on my agenda, so I didn’t scout out the “best” swordsmiths in town, but rest assured—there’s no shortage of places selling everything from ornate sabers to folding knives and other pointy souvenirs. Even if you’re not buying, the craftsmanship alone is worth a closer look. And if you do decide to take home a blade, keep your receipt handy—just in case your train ride back to Madrid comes with a surprise bag check.

One of the Toledo Gates

Streets of Toledo

Puerta de Bisagra

As you can see from above, I stumbled across a handful of photogenic corners that stopped me in my tracks. Because Toledo was a walled city for centuries, there are many city walls and gates you can explore on your walk.

Alcázar of Toledo

Courtyard in the Alcázar of Toledo

Alcázar of Toledo, an imposing fortress that has served as a Roman palace, a medieval castle, and today, a military museum. General Admissions is €5 and opening hours are from 10am-5pm. The fortress is quite big; I recommend allocating at most 2 hours here if you want to fully explore it all. There is a permanent exhibition, structured into thirteen thematic rooms and eight rooms focused on historical path. These rooms showcase the museum's extensive collection of over 35,000 items, spanning various aspects of Spanish military history. I won't lie, some of these corridors and courtyards make for beautiful backdrops for some portrait photography...

Facade of the Alcazar of Toledo

Golden Hour Views

I made Alcázar of Toledo my last stop within the city walls because as the afternoon faded, I wanted to make my way to the other side of the Tagus River to catch the sunset and golden hour. After a quick pit stop for some snacks and water, I exited the same way I entered the old town: through the Puerta de Alcantara. Now, there is an option to take a bus and ride it to the viewpoint I circled above if you prefer not to hike, but there were so many viewpoints along the way where it was definitely worth walking 30-35 minutes to Mirador del Valle.

Viewpoint outside of Toledo city walls

To reach the viewpoint, slip back through the Puerta de Alcántara and follow the Ctra. Alto road. The path is clearly marked, so you won’t have to worry about losing your way. For a dash of adventure, take the rock scramble up to the “Piedra del Rey Moro” viewpoint. Honestly, this was my favorite moment of the trip—a little outdoor side quest I didn’t know I needed. I clambered up to the top, snacks in hand, and stayed for hours watching the sun melt into the horizon. Definitely a great way to decompress. Just remember to budget at least 30 minutes for the walk back to the train station… you don’t want to swap that golden sunset for a frantic sprint to catch the last train to Madrid.

The Last Word

Toledo is more than just a beautiful day trip — it’s a place where the past feels alive in every alleyway and archway. It's also a place where you can bring your comfortable shoes and venture away from the city walls for an amazing view of Toledo as you disconnect from the tourist bustle. This time, I didn’t get to indulge in a local restaurant as I usually do, but if I return, you can bet I’ll be hunting down a hearty Castilian meal… and maybe, just maybe, leaving with a shiny, pointy souvenir tucked into my bag.