Discover the historic city of Toledo on a day trip from Madrid. Choose from guided tours, high-speed train tickets, and combo experiences to explore its medieval streets, stunning cathedrals, and rich heritage.
Day trips from Madrid
Quick, easy, and all in one place—discover the best day trips from Madrid at a glance!
Forget cramming into crowded trains, stressing over rental cars, or playing Tetris with Google Maps. All Madrid day trips come with roundtrip AC transfers that start from central Madrid, so it's convenient whether you're a Madrid first-timer or just not in the mood for logistics.
Ever tried planning a ‘quick’ day trip, only to return and realize you missed something amazing? Not this time. These expert-curated tours ensure you see all the must-visit spots without wondering if you missed a turn or a hidden gem.
A bilingual guide isn’t just there to walk you from A to B—they connect the dots between art, history, and fun facts you won’t find on Google or guidebooks. They’ll translate inscriptions, spot symbols, help you chat with locals, and ensure no historical detail (or menu item) gets lost in translation.
UNESCO treasures surround Madrid, and a guided trip means you can cover a whole city or two (even three!) in a day. Perfect for history lovers, architecture buffs, or anyone with a serious case of wanderlust. It’s the ultimate “make the most of your vacation” move.
After your guide shows you all the cool stuff, you get free time to explore on your own. Wander down hidden alleys, sip café con leche in a sunlit plaza, or hunt for the perfect souvenir—it’s your time to make the day your own.
From quick half-day getaways to full-on historical deep dives, there’s an option for every kind of traveler. Mix and match cities, or stick to just one and explore it inside out. You can even upgrade to include must-see sites like grand cathedrals and royal palaces.
Toledo, Segovia, and El Escorial are top choices. Toledo is known for its rich mix of Christian, Muslim, and Jewish heritage. Segovia boasts a stunning Roman aqueduct and a fairy-tale castle. El Escorial is a massive royal monastery with deep historical significance.
The best months to visit Madrid are April, May, September, and October. Spring (April and May) brings mild temperatures, blooming parks, and outdoor festivals. Fall (September and October) offers cooler weather, fewer crowds, and cultural events like Madrid Fashion Week. Avoid July and August, as temperatures can soar above 35°C (95°F), making sightseeing uncomfortable. Winter months (December to February) are quieter and budget-friendly but can be chilly, especially in the mornings and evenings.
For a weekend escape, Córdoba, Valencia, and Seville are great choices. These cities are easily accessible by high-speed train and offer unique cultural experiences.
Visit the Catedral Primada, Alcázar of Toledo, and Monastery of San Juan de los Reyes. Art lovers should explore the El Greco Museum. The city’s medieval streets and historic atmosphere make it an unforgettable destination.
September is ideal, with cooler temperatures and fewer crowds. It’s also a great time for cultural events and outdoor exploration.
Madrid’s cocido madrileño, Toledo’s carcamusas, and Segovia’s cochinillo asado are must-tries. Each city has its own distinct flavors.
If you’re booking a guided tour, it’s best to book at least a week in advance to secure availability, especially for peak seasons like April-May and September-October. If you’re traveling independently, train and bus tickets can be booked a day or two before, though booking in advance can help you get better prices.
Wear comfortable walking shoes, as many cities like Toledo and Segovia have cobblestone streets and steep hills. In summer, light clothing, sunglasses, and sunscreen are essential. In winter, bring a jacket or coat, especially if visiting colder regions like Segovia.
Yes. Do it only if you are booking the full-day covering both cities as they are well planned and paced. But if traveling independently, it’s better to dedicate one full day per city to explore properly and not feel rushed.
The trip was perfect in a number of ways. The 6 hour, half day tour was perfect for the amount of time we had and what we hoped to see. From the 55mins bus trip and return to Toledo, the running commentary in English and Spanish to the tour of the forge and gold establishment ( where lots of gifts for home were bought) to the grand tour of the castle and city on the mountain. Everything was pretty much magical that exceeded expectations. Ka nui te mihi aroha ki te taonga o te kaupapa o tenei rā. Ka rawe hoki rā. From New Zealand Manu and Tui.
The historical tour through the historic center of Toledo was excellently explained by the guide Mariano...a genius...and the beauty of that city...imposing!
The city is beautiful and its history, narrated by the guide Javier, very interesting. It is a pity that we did not have time to see the Cathedral inside as it was a half day tour.
It was a lovely tour with very nice guides. I recommend it to everyone! Toledo is extremely beautiful🙂
They had the wrong starting point on the website, and we had no idea the meeting point was that far since we booked last minute. And when I called the support team, only machine no people. Terrible experience. Literally dont care about you once you booked the tickets
Nothing, since i never was able to take trip.
Ticketing experience was great ..no problems The trip was really great..informative and I felt I got to see a lot of Toledo just on that half day trip. Our guide was fun and enthusiastic
Great experience. The tour guide had very good knowledge of the city of Toledo and the history. It was the perfect half day tour.
Comfy bus on way to Toledo. Great picturesque town that I suggest anyone should visit if in Madrid. Tour guide was detailed without talking too much. Great day out. Sit on the left side of the bus for best viewing and pics.
There was not much of a tour. Mostly just free time. The host was knowledgeable but had to do the short tour in both English and Spanish
Great if you don't have much time. Guide was very knowledgeable and trip was well organised and kept to time. Would have been nice to take a bit more 'own time' to look around at our own pace. Just 20 minutes or so.
The gaudiest was very nice. And the tour was very well organized
easy and clear instructions where to meet. Nacho was a great guide. wish we had more time to explore on our own.
If you are short on time, book this half-day tour and see the best of Toledo in 6 hours.
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Manu
Selva
Carlos
Sightseeing, plan and punctuality however, it could be 1 more hour as everything was in rush، we must be at coach at sharp 4:30 and we just finished Cathedral around 2. This is the only cons it had
Instructions were clear and Toledo was lovely. We changed guides once in Toledo and I feel it would have been great if she had used a microphone like some guides from other tours. There were a lot of people a lot of noise making it very hard to hear her. She did her best under difficult circumstances.
Easy ride from Madrid to Toledo and back. I liked the explanation about Toledo upon arrival and the view point. Unfortunately there was also a 'factory visit' of damescene jewelry, a real tourist trap which took precious time (45 minutes). This was not advertised and such damescene could be bought in many shops in town as well. The tour in centre of town and cathedral was nice.
Organized, punctual, as expected and fun.
It lasted 7 hours instead of 8 like it was said when i bought tickets.
A charming and very interesting guide.
Excellent The guide Cris was very friendly and attentive.
The guide was excelente!! We erre few perdón, that s maje the diferente
A good tour with excellent price to go and return to Toledo. The guides Benito and then Eva shared with us good information to be able to make our visit to this beautiful city. Thank you for taking care of everyone's time and leaving as punctual as possible as there are people who may have tickets later returning from Toledo.
Our trip to Toledo was awesome. Meeting place was easily accessible. The transaction was a nice modern bus and our guide was very knowledgeable and answered all our questions. Personally I think the return can be scheduled to earlier since unless you have tons of things to do, the free time is a bit too long
The transportation was punctual, although they should describe a little more precisely the meeting point in Madrid because the area is large and there were doubts. The guide in Toledo explained everything clearly about the city and provided maps to go to the most iconic places.
Pila such a fantastic English speaking guide! She's knowledgable and funny. She made it very interesting, I immediately fell in love with Toledo!
Excellent attention from Lidia and the driver, very punctual.
Deep dive into Toledo! This tour packs art, history, culture and landmarks in a single day.
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Starting point: Madrid
Toledo Old Town
St. Tomé Church
Santa María la Blanca Synagogue
San Juan de los Reyes Monastery
Real Colegio de las Doncellas (if option selected)
Cristo de la Luz Mosque
1.5-hour free time or lunch (if option selected)
Jesuitas Church (if option selected)
El Salvador Mosque-Church (if option selected)
Toledo Cathedral
Mirador del Valle viewpoint
End point: Madrid
Nicolaas
Ramin
Wonderful experience. Knowledgeable tour guide, with a good sense of humour. Very picturesque cities, trust me. Picturesque in a sense it will make you friends jelly after posting a few images on the socials. If you like history, social dynamics between different ethnicities, religion integrating or the opposite. I say go for it
The guide explained everything in detail, journey was very comfortable, great places to visit
The guide wasn't at the agreed place, we paid in Spanish and most of the time she spoke in English, giving different explanations in both languages. She left us without support in both cities. We ended up getting lost in Toledo. She gave us the name of a square to meet in that didn't exist. We asked her if we got lost and she told us to look it up on Google. She drew attention to herself in front of other passengers. In Segovia, when we arrived at the Alcazar, we asked to return with her and she told us we couldn't return with her. She left us alone on the tour. We were disappointed with this guide. We've done several tours with you and it was good.
I have very bad experience as the instructions email direct me to wrong pick up location and nobody pick me up at meeting point. Before 10min expired I use the chat contact Headout email but no body help and I called IBE tour and they said the tour bus already gone as I went to wrong pick up point. I have send all proved photos and chat screenshots to proved I arrived meeting point at 8 am followed by email. It was spoiled my day and I am still not received the refund.
Both cities are very beautiful and with a great history, the guides are very dynamic and with great mastery of the subject... I liked everything
Excellent service. The only thing I think is that they should redistribute the time in each city. 30 minutes more to Segovia and if they want to return the same at 5:45pm, then 30 minutes less to Toledo. It would be perfect!
Very good guide, very comfortable and clean bus, very good time management
The trip was organised well. The bus was very comfortable. The guide spoke very good English and provided very good information. It might be good to have more time in Toledo.
Our tour guy was excellent and the places were fantastic
Knowledgeable guides giving the exact level of detail I was after. Unlike other tour operators, they weren't too rigid with the time and meeting points which allowed me to feel more relaxed without delaying the entire trip and itinerary
Tour guide Amanda was brilliant and made the trip very interesting. She has probably delivered the tour dozens of times but it didn't come across like this at all. Both cities memorable and worth a visit. Excellent all round
Cover all the main highlights of 2 UNESCO cities in the language of your comfort.
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Starting point: Plaza Las Ventas
Toledo
Walk the narrow historic streets and pass by gems like the Monastery of San Juan de los Reyes. Upgrade to add on tickets to the majestic Toledo Cathedral.
The enchanting city of Segovia welcomes you with its ingenious Roman Aqueduct. Upgrade to add on tickets to the iconic Alcázar.
Go-molemo
Sergio
Miguel
Toledo, Segovia and Avila were beautiful places that we could have easily stayed at. Our guide was very knowledgeable and attentive.
Very top class management. Well disciplined trip. Joyful and informative demonstration of Mr khan sir 👏 😀
1. We were never given a audio device. You need to provide one for each customer. You aren't thinking about people with trouble hearing. 2.Guides didn't direct you to the correct guide when they split you according to language preference. Very unorganized tour guides. I over heard them talking bad about people in their group. The only time a guide did a head count was when the bus was leaving. When split up they never took a head count. The never looked back to make sure the group was together. It was extraemos hard to keep up. As soon as a guide stopped to explain they never waited dor everyone. They should have noticed half of your group is still reusing to catch up. Because they never checked by the time we reach the guide she's done explaining. They never wanted to repeat. It was horrible. We weren't given enough rime to go to the bathroom. You have to think we aren't the only tourist. Guides don't wait not 1 min past meeting time. They have no problem leaving you behind. Again that's also part of not counting how many people in the group. 3. We were never given time to stop and buy anything. 4. Avila shouldn't even be a part of this tour. You show is 2 things and take us to a store to get some type of candy which is part of our time to explore and after that we go back to the bus. Useless tour! 5. This is a very fast walk thru each town. This tour should not exist. 6. I have used head out last year for my travels and loved my tour guides. This year not so great. 7. I know for a fact other people on this tour have said they called to complain.
We had two guides. Ainoa in Toledo and Segovia. She was very kind, considerate and very clear in her explanations and timing. Monica was our guide in Avila and her explanations were also very clear, although fast because she had to explain twice (English and Spanish). In Avila the visit is very short and we would have liked more time to visit the Cathedral. Excellent service and attention from everyone.
Juggle 3 UNESCO cities in a day with a well-rounded itinerary and a bilingual guide.
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Check the location shared on your final voucher to meet your guide and board your comfortable transfers for the day.
Walk the narrow historic streets, and pass by the Monastery of San Juan de los Reyes.
This enchanting city welcomes you with its ingenious aqueduct, iconic Alcázar, and beautiful Segovia Cathedral that towers over the highest part of town.
Surrounded by 11th-century walls, beset by an enormous Roman necropolis, discover the city's historic center – a UNESCO World Heritage Site.
The guide was very attentive and competent
Ditch the planning woes! Tour 2 UNESCO cities in a lux AC bus and savor authentic tapas.
Inclusions
Full-day tour of Segovia & Ávila
Expert English and Spanish-speaking bilingual guide
Pick-up from Madrid
Round-trip transfers in a luxury AC bus
Entry to Segovia Alcázar(as per option selected)
Tapas and wine/beer/ soft drinks
Exclusions
The town of Segovia itself... The guide from Madrid to Segovia was inaudible in the coach, and I didn't hear a word he said. The city tour was more interesting with this guide, thanks to the headphones he gave us, and he was not at all friendly and introduced himself in a neutral and banal way, obviously not happy to be there that day... I only took a brief tour of part of the city with him: no meal, no Alcazar and no Cathedral. On the other hand, on the return journey from Segovia to Madrid, the guide was much friendlier, greeted us with a smile and apologized for the bus being late due to a passenger's accident, and gave us some interesting information before arriving in Madrid: the history of the four skyscrapers, the Picasso tower and its owner, the "boss" of Zara, etc. .... The personality of a guide, in addition to his professional skills, seems to me to be indispensable...a smile, a little joke and everyone is in a good mood.... But that's rare these days...only the pay slip counts for some...
Was able to find cheap tickets at the very last minute! Will definitely use this app again
Reliable and good communication. Thank you!
Great price and deals. Helpful folks on chat!
This app keeps everything organized for you. If I’ve had a question they have answered. Use the live chat.
Excellent service. Keep the Good work
Everything was clearly explained and worked as promised
Easy to book, choices were clearly shown and the instructions were great
Easy and very pleasant experience
we booked for a group of 10. So much fun!
Faster option
We are very happy with the experience on Headout
Easy. Immediate receive of tickets.
Everything was amazing !!! Friendly staff thank you very much for all !!! Change nothing !
Deep dive into Segovia's layered history on a full day guided tour of must-see landmarks.
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Full-day tour of Segovia
Expert English and Spanish-speaking bilingual guide
Pick-up from Madrid
Round-trip transfers in a luxury AC bus
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Unravel Spain’s history in a day with stops at El Escorial, Valley of the Fallen, & Segovia.
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We were unable to travel due to illness
See Spain's oldest walls and university in a full-day guided trip, complete with transfers.
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Full-day tour of Ávila and Salamanca
Expert English and Spanish-speaking bilingual guide
Pick-up from Madrid
Round-trip transfers in an AC bus
Entry to Salamanca's Cathedral
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Food and drinks
Entry to monuments of Ávila
Super punctual, well organized and the guide was friendly and explained everything in detail.
Excellent guides. Very kind. Congratulations.
Skip the lines and explore two Spanish landmarks on a half-day guided tour with transfers.
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You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Book now without paying anything. Cancel for free if your plans change.
I am waiting for my money back since the activity was cancelled due to the guide's illness. They did not offer another one in exchange that we were not interested in.
The guide was very kind and explained the whole tour very well, we liked it very much 👍🏻
Very nice guided tour very interesting
This tour comes with entry tickets and a bilingual guide for unique insights.
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