There are plenty of other day trips near Madrid, but none compare to Toledo. Toledo is a must-visit destination for its history, culture, and stunning views. It’s the number-one day trip from the Spanish capital, but it’s easy to miss out on the great gems this historic place holds. To see the city with an expert guide – and make the most of your time in Toledo – join our Small Group Toledo Day Trip from Madrid with Winery Tour.
At Walks, we’re committed to smaller and more intimate tour groups. With fewer people around you’ll become immersed in your surroundings and really feel part of an experience.
See the best of Toledo in just one day
A crossroads of three religions – Arab, Jewish, and Christian – Toledo isn’t just another stop near Madrid. It’s a millennia-old city full of history and culture. With many nicknames, such as “Toletum” and “the Imperial City,” you know there must be something special about it.
When you visit Toledo, you’ll learn about the significance of each nickname and gain insight into its fascinating past. Uncovering hidden gems and learning fascinating stories about Toledo’s history, traditions, and culture will keep you engaged all day. After your visit, you’ll certainly understand why the city of Toledo has UNESCO World Heritage status.
Sit back and relax – we’ve planned the perfect itinerary
We have taken care of everything for you, so there’s no need to worry about logistics. From transportation to monument entry, mid-morning snack, and guided tours, you won’t have to worry about a thing. We’ve got you covered.
If you’re worried about getting lost in Toledo’s labyrinthine streets, fear not! With our amazing guides, you won’t have to worry about navigating the maze-like city. They will guide you through the city’s streets, alleys, and plazas, allowing you to relax and enjoy your time there.
Toledo’s winding streets are more approachable with a friendly guide.
Local guides bring the city to life
Our expert guides are a perfect blend of storyteller, insider, and passionate Spain expert. From taking a walking tour of Toledo’s historic center to exploring a 13th-century cathedral, our guides truly bring the characters, history, and food of Toledo to life.
Discover special views you’d miss when traveling by train or bus
The views in Toledo are breathtaking. The tour starts high up over the city, providing you with panoramic views of Toledo before entering the city itself. Later, you’ll visit a vineyard that is not open to the public. Nicknamed “nature’s classroom,” you’ll take in the fresh air while learning about the region’s winemaking history.
Get local recommendations and insights
Throughout the tour, your guide will offer additional recommendations for other notable restaurants, sites, and attractions in Toledo. You’ll get to explore the city like a local and discover hidden gems you might otherwise have missed.
Enjoy an exclusive winery visit
We believe in experiencing Spanish wine the way Spanish people do. Instead of visiting an overcrowded winery with a big name, we take you to a smaller winery producing high-quality, limited offerings. You’ll have a truly private visit with the owners and family themselves to learn about their winemaking process.
From our winery partners
We love sharing what we do with visitors, because we are proud of and satisfied with what we do. In a way, it is like giving back to society what nature gives us with its fruit, the vine. In fact, our motto is "respect and love for the countryside and its fruit". - Pedro, the owner of the winery we visit.
This winery is not open to the public, making it an exclusive experience for our guests. It’s off the beaten path but in a historic wine region.
Interactive activities create memorable experiences
Have you ever wanted to make wine? At the winery, you put the finishing touch on the bottles to seal them with wax! You’ll have to join to find out what that entails, but we can assure you it doesn’t involve stomping grapes unless you want to!
Curious travelers love our tour
We’re always thrilled when guests appreciate the insights they gain from our tours. Here’s what previous travelers have said about our Toledo day trip from Madrid.
What guests say about the Toledo Day Trip and Winery Tour
“I’ve been to Toledo before, but it was much more enjoyable going with a guide. I appreciated that we had some free time in Toledo to visit shops and buy souvenirs. The visit to the vineyard felt really special as they only do tours with Walks. I wouldn’t have been able to get there on my own and really enjoyed that part of the day. I loved that I could visit a major city like Toledo and check that off my list while also doing something off the beaten path by going to the vineyard.” – Halley R
“100% recommend this tour to anyone who is interested in Spanish history and culture. The vineyard experience was amazing! They explained the process from how the grapes are grown to how they are fermented and then finished off with a delicious tasting! Shout out to Sean the guide who was brilliant!” – Jemma H
“The rain did not tarnish this wonderful day. I have always wanted to visit Toledo and I kept delaying this trip. This excursion is perfect to cross this destination off your list. From the moment Sean greeted us, I knew I was in good hands. It’s not easy to get it right when you’re traveling by yourself, but the very comfortable coach (with USB chargers to have your phone’s battery 100% charged for the thousand photos you’ll take!), the good company of a small group of like-minded travelers, and the bottomless well of wisdom of our guide, made this experience one that I will always remember.
The ride to Toledo passed by quickly while Sean gave us some tips and context of what we saw, about Spain’s History and his own experiences as a Toledo citizen.
Toledo is flooding in history, our guide helped us navigate it and understand the historical and cultural importance of this site.
I would have never had the same experience just hopping on a bus and roaming the streets.
The trip did not feel rushed, we even had some time to explore on our own and a coffee break before hitting the city, which is nice.
After some time roaming the streets, the trip was not over! We returned to the bus to go to an amazing off-the-beaten-path destination close-by. What a change of scenario! Once the streets of Toledo started to get busy we entered a nature wonderland: Holm oaks, olive trees…and vines! We were the only ones allowed in Pedro’s organic winery and it felt really special to hear the story of these wines from him, directly. You can even wax your own bottle if you want to take one home (and you will take at least one home)” – Suz E
Our Toledo and winery experience is a must-do day trip from Madrid. With its history, culture, stunning views, and exclusive winery experience, you won’t want to miss out on this unique adventure. So, what are you waiting for? Book your Toledo and winery experience today and explore this fascinating city with us!