Small Group Toledo Day Trip from Madrid with Winery Tour

47 reviews

8.5 hours

Max 16

Why take this tour?


  • Drink in postcard-perfect views of the storied city of Toledo from a beautiful viewpoint.
  • Embark on a walking tour of Toledo’s historic center and discover why it’s known as the “City of Three Cultures.”
  • Learn what makes Manchego cheese and Spain’s famous ham so delicious while tasting it for yourself at a small gourmet shop.
  • Step inside Toledo's ornate cathedral and learn to appreciate the breathtaking details with insight from your guide.
  • Explore a family-owned winery and enjoy a tasting of their own biodynamic wines.
  • Sit back and relax as we make our way to each of the day’s destinations—we’ve arranged comfortable, air-conditioned private transport so you don’t have to worry about logistics.
  • Sites Visited
  • Toledo viewpoint
  • Jewish Quarter
  • Plaza Zocodover
  • Synagogue (inside)
  • Cathedral (inside)
  • Church of Santo Tomé (exterior)
  • Family-owned shop with cheese and ham tasting
  • Family-owned winery & vineyard
  • Tour Includes
  • Entrance to Primada Cathedral
  • Entrance to Synagogue of Santa María la Blanca
  • Round trip private transportation with AC
  • Food tastings: ham & cheese and other products
  • Entrance to vineyard with winery tour and 3 wine tastings
  • Expertly guided walking tour of Toledo
  • Local English-speaking guide
  • Small group of 16 guests maximum

Enjoy a perfectly planned escape to La Mancha.

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Total Customer Reviews: 47

Verified Ratings
4.9 /5
based on 28 Walks' reviews
Rating summary by category
Guest Support
Latest reviews
The tour only got better and better. We started visiting the jewish neighborhood in Toledo and the historic center. Lola our tour guide told us about the rich history and cultural mix that happened here. we visited a Sinagoge and the Cathedral. we said good bye to Toledo by having a cheese and wine tasting. Then we headed to a small lovely town to visit a vineyard ( that was my favorite part). this is a family owned business where we tried different wines. We were lucky as we were able to see the different grapes as its vendimia time and see the winery.
Tripadvisor customer · Sep 15, 2023
Amazing historic city. Knowledgeable and affable guide. Delectable nibbles and sips with artisans whose joy in their products was infectious.
Tripadvisor customer · Sep 14, 2023
I had an excellent time and enjoyed every moment. I feel like I got the full Toledo experience, something that would never have happened had I gone without a proper itinerary. Bear in mind it is a long day (about 9 hours in total) - so you do get your money's worth in that respect. And you'll get your steps in for the week. The first stop overlooking the city was a great way to begin as you could some of the locations you were to visit, such as the Synagogue of Santa María la Blanca and the impressive gothic Primada Cathedral. The little windy streets and old buildings were both quaint and impressive, although watch out for the cars as they don't seem to care much for pedestrians. Lola was a great tour guide - knowledgeable, warm, friendly, and experienced. I liked the mix of different activities and how they flowed together. For example, the cheese and wine tasting slotted nicely after the walking tour of the landmarks. Likewise, the winery was a nice touch after a 30-minute break, so we had just enough time to recuperate. Highly recommended.
Tripadvisor customer · Sep 14, 2023
This tour was fantastic! The guide could not have been more friendly and insightful, and really took time and care to engage the group, make sure we were happy and comfortable. It was great to get to know Toledo early in the morning before the crowds came in, and to experience several different activites throughout the day. The highlight was definetly the winery visit where the owner was so friendly, and the wines were delicious! One other final detail: being summer in Madrid, it was very hot, but having private transport w/ AC made all the difference. It was overall a great experience that I recommend to others.
Tripadvisor customer · Jul 24, 2023
This experience was an amazing deep-dive into such a fascinating city! I loved that we started our day that bit earlier to avoid the crowds (and the summer heat!) and the historic walk through the city gave us a chance to not just learn about the complex history of Toledo, but see it represented in the architecture and landmarks too. The winery was the cherry on top - local, family-run, small production, everything I look for in a winery experience - would absolutely recommend!
Tripadvisor customer · Jul 11, 2023

Meeting Point

Meeting Point Map ⟶

Meeting point

Plaza del Emperador Carlos V, 9, 28012 Madrid. We will meet outside the coffee shop called Rodilla, which is next to El Brillante bar. Your guide will be holding a green Walks sign.

Please meet 15 minutes prior to the tour start time.  


Is this tour accessible for wheelchairs, strollers or for those with mobility impairments?
Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments, or for wheelchairs or strollers. Please contact the Guest Experience team at [email protected] or call +39 068-596-0143 (Italy) or 888-683-8670 (USA) to make alternative arrangements.

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