If you’re in Spain, you can’t just not go to Madrid – with its gorgeous boulevards, buzzing tapas bars, amazing music, and world-class museums, it commands attention.

However, you’d be remiss to not make your way over to the fairytale-like medieval town of Toledo, which feels like it’s been frozen in time. Situated just an hour or two from Madrid, Toledo offers everything from ancient monasteries to rolling vineyards.

If you want to streamline logistics and really make the most of the experience, I highly recommend taking one of the 5 top Toledo day trips from Madrid, that are well worth your time and money. Let’s get started!

Be sure to see our reviews of Madrid Flamenco Shows, Tapas Tours and Segovia Day Trips.

Best Toledo Day Tours From Madrid

	Three Cities in One Day: Segovia, Avila & Toledo from Madrid	Toledo Private Tour with Licensed Local Guide	Toledo City Tour, Winery Experience & Wine Tasting from Madrid
Location:	Pl. de San Miguel, 7, Centro, 28005 Madrid	Hotel pickup and drop-off included	Pl. de San Miguel, 7, Centro, 28005 Madrid
Start:	8:00 AM	Between 10:00 AM & 3:30 PM	9:00 AM, 10:00 AM, 11:00 AM
Duration:	12 hours	3 to 8 hours	8 hours
Includes:	Bus transportation, Guided tour of Segovia, Ávila and Toledo, given by a professional guide, Lunch in a local restaurant, Entry to the Primate Cathedral of Toledo	Expert local guide with license Skip-the-ticket line at the Cathedral (Admission ticket at customer's expense), Private tour, Private round-trip transfer from Madrid SELECTED)	Visit Toledo, Visit a Winery from the XVIII Century, Taste 3 Selected Wines with snacks, Explore vineyards, Air-conditioned bus transportation
	Tour Information & Booking	Tour Information & Booking	Tour Information & Booking

Quick Answer: The 5 Best Rated Toledo Day Trips For 2025

1. Three Cities in One Day: Segovia, Avila & Toledo from Madrid
2. Toledo Private Tour with Licensed Local Guide
3. Toledo City Tour, Winery Experience & Wine Tasting from Madrid
4. Segovia & Toledo Full Day Tour from Madrid with Optional Alcazar
5. Toledo and Segovia Private Tour with Hotel Pick Up from Madrid

Toledo Day Trip Reviews

1. Three Cities in One Day: Segovia, Avila & Toledo from Madrid

It’s not uncommon for people to only visit the major cities within a country – after all, those are the places that are more commonly covered in travel blogs and channels.

However, just beyond the city borders are oftentimes incredible hidden gems filled with history and unique architecture, just waiting to be explored – and with a proper guide, all logistics are taken care of for you.

The Three Cities in One Day: Segovia, Avila & Toledo from Madrid is perhaps a whirlwind trip but ensures that you really maximize your time in Spain in the best possible way.

Your tour starts out at 8:00 am to make the most of the daylight and avoids most traffic, taking you in comfortable, air-conditioned transportation to the Roman aqueduct of Segovia first.

As we traveled along, our guide did a great job of sharing information about the surrounding areas we passed by, as well as more specific historical and cultural commentary about Segovia. Seeing Alcazar – a castle that felt like it belonged in a Disney movie – was absolutely breathtaking, as well as the fascinating Jewish quarter, breathtaking natural scenery, and the grandiose mansions.

We then hopped back onto our bus to make our way to the Game of Thrones-esque fortress city of Avila, which boasts amazingly well-preserved medieval city walls that completely surround its city center.

Our guide did a great job with his storytelling, recanting tales about it being the birthplace of the Catholic Saint Teresa of Avila. It features one of the highest number of Romanesque and Gothic churches per capita in the entire country, so you’re in for a real architectural treat here!

While you totally don’t have to, I recommend opting for the lunch option, so you can fuel up on traditional Iberian dishes in one of the oldest restaurants in the city! If you choose not to, of course, you have a bit of leisure time to explore and choose other food alternatives.

Last but not least, you’ll make your way to the gorgeous hilltop town of Toledo, where we learned why it’s known as the “City of Three Cultures”, and got to take photos at the amazing Gothic cathedral and at a stunning lookout over the river valley.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

2. Toledo Private Tour with Licensed Local Guide

Perhaps you have a busier schedule or are shorter on time and won’t be able to make the longer tours fit into your itinerary – this tour is for you! The Toledo Private Tour with Licensed Local Guide lets you tweak your itinerary to your liking, working around your other plans.

You don’t have to worry about the hassle of dealing with driving there yourself, nor do you have to worry about the tour focusing on things you aren’t interested in – this one is all about you.

Something that I’ve felt on a few standard tours over the years, is being rushed through sights I found interesting, which I’m not always able to go back to and explore further. This tour eliminates the chance of that happening, as you get to select either a 2-hour or 3-hour excursion that suits you best.

Focus on the Toledo sights that catch your attention most, and skip the ones that can be left to the side. I loved that our guide organized with us a couple of nights before on the perfect pickup time, arriving right at our hotel lobby, so we didn’t have to fret about meetup points at all.

We boarded a private vehicle with lots of legroom, climate control, and nice windows ideal for watching the beautiful scenery go by while our guide regaled us with fascinating historical accounts.

Keep in mind that as this is a private tour, my itinerary may not be exactly the same as yours, but if you need help, your guide is there to offer their expertise in crafting a plan that you’re sure to love.

As we were mostly interested in architecture and culture, we had a ton of different options, walking through the Christian, Jewish, and Muslim Quarters, stopping at iconic landmarks like Alcazar, the mosque, synagogues, and breathtaking cathedrals dating back hundreds of years.

I felt so lucky to also see some work from El Greco, where we actually got to see the legendary “The Burial of the Count of Orgaz”!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

3. Toledo City Tour, Winery Experience & Wine Tasting from Madrid

I don’t know about you, but I’m constantly on the hunt for great wine while I travel, which has brought me to some very happy surprises. Visiting Toledo was one of them, and I knew I had to go all-out, so I chose the Toledo City Tour, Winery Experience & Wine Tasting from Madrid!

Aside from the fantastic drink, I’m going to go out on a limb and say this was one of the most well-organized, fun tours I’ve ever been on of any kind!

This 8-hour experience kicks off in the morning with you meeting your guide and the rest of your small group in the city center of Madrid, boarding an air-conditioned coach to head out to the Imperial City: Toledo.

Sitting high above the Tagus River, you can expect absolutely phenomenal views (great photo ops!), and essentially a time capsule presented to you in real life.

Walking the medieval streets does feel like stepping into another era, where knights, kings, and queens were still part of the norm and three religions coexisted (not always peacefully, but sometimes!).

Our guide took us on an educational walking tour through the Jewish Quarter, followed up by nearly an hour of leisure time for us to explore as we saw fit! We chose to explore a couple of sights a bit more in-depth before grabbing a delicious lunch and coffee, then headed back on the coach.

We made a stop at Bargas where we saw and learned about the 200-year-old vineyard before heading down into the cellars for a fantastic tasting and lessons on aging and stabilizing.

I don’t know if it was because our tour guide clearly had a solid relationship with the winery owners or what, but we were even lucky enough to sample wine right from the barrels! All in all it was a magical day full of just about everything I love, along with great company!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

4. Segovia & Toledo Full Day Tour from Madrid with Optional Alcazar

This next tour is one of the most comprehensive experiences you could have while visiting the towns surrounding Madrid – yes, it clocks in at a whopping 12 hours, but you’ll be glad you did it!

You’ll see everything from the major sites to plenty of historical and cultural gems, with an expert guide there to lead the way, sharing his passion for these amazing places with you. The Segovia & Toledo Full Day Tour from Madrid with Optional Alcazar excursion is just the right amount of time to become acquainted with both cities, with flexible options along the way.

Starting off in the city center of Madrid at 9:00 am, you’ll meet with your guide and the rest of your group and board your comfortable bus complete with big windows ideal for sightseeing as you cruise along.

Our guide was amazing and her passion was palpable right from the very beginning – with amazing storytelling that really brought the old buildings and art to life. As soon as we got out to the Spanish countryside, my stress started to melt away, and it only continued to do so throughout our day.

Our first stop was at the infamous Segovia Aqueduct, which is one of the most well-preserved, elevated Roman aqueducts in the world! As an architecture nerd, that alone was worth it for me, but we then followed that up with the Gothic Roman Catholic Cattedrale Di Segovia, which is an absolutely insane, intricate 16th-century church. Of course, there’s no way we could forget the Alcazar, which stretches up above the meeting of 2 beautiful rivers – it’s currently used as a museum but still holds its charm and intrigue.

We then made our way to Toledo, stopping first at its stunning Catedral Primada de La Santa Maria – one of the few 13th-century High Gothic cathedrals in all of Spain! We then learned all about and walked around the Alcazar of Toledo, which has an incredible amount of history, with some stories even connecting it to Mexico!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience

5. Toledo and Segovia Private Tour with Hotel Pick Up from Madrid

Last but certainly not least, is the Toledo and Segovia Private Tour with Hotel Pickup from Madrid. If you want to do things a bit more “VIP”, then you’re in the right place, because this tour thinks of everything.

No big tour buses, rushed itineraries, and the seemingly endless crowd of heads snapping photos instead of focusing on where they are and what could be learned. If you’re at all interested in history and or breathtaking architecture, please put this one right at the top of your list!

Your tour also starts out early in the morning, with your guide coming right to your hotel lobby to pick you up – no dealing with the hassle of meetup points or booking separate transportation!

Our guide was lively, friendly, and incredibly knowledgeable, sharing tons of fun and interesting stories as we cruised along the beautiful countryside. Our first stop was the medieval town of Toledo, which uniquely blends architecture and influence from Moorish, Jewish, and Christian cultures.

You’ll learn all about how that came to be in the first place, and how the three cultures got along so well…then not so well. There’s the cathedral to soak in, all kinds of Gothic drama, and El Greco’s masterpiece, which was amazing to see, all on its own.

We then hopped back on our transportation to arrive in Segovia, where we saw the legendary aqueduct and the towering Alcazar sitting high above the city. Have you ever been to a castle only to learn that it was only ever used as a residence – no dramatic battles or overzealous rulers getting out of hand?

Well, that’s not the case here – while it was indeed built as a defensive structure, it later on served as a state prison and military academy, which provided quite the stories. Expect to see so many more sights and viewpoints, as this is one of the most comprehensive, detailed tours of its kind!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience