Half-Day Toledo City Tour with Winery Visit from Madrid

From Madrid, explore the City of Three Cultures alongside an expert guide and sample 3 select wines

Travel Flexibly · 8.00h · Madrid, Spain

Did you know just an hour from Madrid sits the vineyard-surrounded city of Toledo? And that with an insider's help, you can experience its hidden wonders for yourself on a half-day trip? This tour, featuring a guided exploration of Toledo’s Jewish Quarter and a wine-tasting session at a family-run winery, ensures a well-rounded introduction to the region. With every detail planned and comfortable transportation, you can look forward to a stress-free excursion filled with memorable moments

  • Meeting Point is at Plaza San Miguel, 7. Madrid
  • Mirador del Valle
  • Plaza Zocodover​
  • Jewish quarter​
  • Cathedral of Toledo​
  • Winery visit
  • Vineyards
  • Learn from a sommelier!​
  • Finish your tour at calle Bailén, 25

Your memorable half-day trip begins in the morning in the centre of Madrid, where you’ll meet your group at Plaza de San Miguel, 7 and hop into a comfortable mini-van bound for Toledo. Upon arrival, learn about the balance of Christian, Muslim, and Jewish influences during a guided walking tour through the Jewish Quarter and to the Cathedral of Toledo.

After free time in Toledo to explore independently, your trip continues with a transfer to a scenic winery tucked in the surrounding rolling hills. Here, an expert sommelier will reveal the region's secrets while leading you through the vineyard and into the cellar for a tasting. Unfortunately, all good things must end, and early in the afternoon, you'll settle in for the hour's transfer back to Madrid.

Half-Day Toledo City Tour with Winery Visit Description

Your 8-hour tour includes:

  • Guided tour of Toledo with an official guide

  • Free time to explore Toledo

  • Visit to a family-run winery in the Toledo Region

  • Vineyard walk and wine-making insights

  • Wine tasting of 3 select wines with tapas pairing

  • Comfortable round-trip transportation from Madrid in a luxury mini-van

  • Small group experience for a more personalized tour

  • Departing From Madrid

Your adventure begins in Madrid’s Plaza de San Miguel, where you’ll meet your official expert guide and board a comfortable luxury mini-van along with a few other like-minded travelers. Soon, you’ll be making your way out of the lively city, alongside olive groves, and through quaint towns to the hilltop town of Toledo. Known as the "City of Three Cultures," you’ll immediately swept away by Toledo’s impressive yet diverse architecture, which has been influenced by Christian, Muslim, and Jewish residents.

Explore Toledo

Your time in Toledo starts with a guided walk led by an official expert. Thanks to their local knowledge, you'll be let in on the city's fascinating stories as you meander through the Jewish Quarter's winding streets dotted with synagogues and quaint shops. You'll also be led to the magnificent Toledo Cathedral, a masterpiece of Gothic architecture.

After the guided tour, you'll have time to explore Toledo on your own. Wander through the labyrinthine streets, grab lunch at one of the local taverns offering delectable Spanish dishes, or perhaps find a cozy café to sample Toledo’s famous marzipan. Just keep an eye on your watch, as it’s time to bid well to Toledo.

A Taste of Toledo’s Wines

Back in the van, your journey continues through rolling hills to a traditional winery. Here, you’ll meet an expert sommelier who’ll teach you the secrets of Toledo wines as you stroll through a vineyard and head inside a charming wine cellar. Surrounded by aging wine, you’ll sample three different varities, each chosen for its unique flavors that are characteristic of the region. Along with the wine, delight in perfectly paired bites and tapas.

As evening approaches, it’s time for your return to Madrid. Board the comfortable mini-van once again and settle in for an hour's ride, and before you know it, you’ll be back to Calle Bailén, 25, right next to where your adventure all started. Yet, with this carefully curated trip, you’ll be carrying with you many memorable moments and photos to go along with them.

What you get with this tour
Explore Toledo City
Cathedral of Toledo
Gothic Quarter
Visit 200-year-old winery
Taste 3 select wines
Expert guide and sommelier
Return transport from Madrid
Small group size of max 30 people
Ticket for entry
Access to the 1st level glass floor
Elevator access the Summit Level
World class views of the Paris skyline
Passionate English-speaking guide
Roundtrip transportation
Wine tasting
Winery visit
Group size of max 30 people
Guide gratuities
Hotel pick-up and drop-off
Food and beverages
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Frequently Asked Questions

What to bring?

We suggest wearing comfortable shoes, and dressing according to the season. Please also bring a valid ID and a thirst for wine knowledge!

Where to meet?

You will meet your guide and group in Plaza San Miguel, 7 Madrid. Ending point is in Calle Bailén, 25. Madrid

What to bring?

We suggest wearing comfortable shoes, and dressing according to the season. Please also bring a valid ID and a thirst for wine knowledge!

Is this tour run by The Tour Guy?

This tour is operated by one of our trusted and vetted partners in Madrid

What if I have concerns about my mobility on this tour?

If you have any doubts about your mobility, please let us know beforehand and we will do our best to accommodate you. The tour includes walking on uneven terrain and navigating steep staircases

What happens if it rains?

We run our Toledo City and Winery tour rain or shine. If the weather is extremely bad and we cannot proceed with the tour, we’ll inform you as soon as possible

Is there any chance my tour might be canceled?

On the rare occasion the tour is canceled, we'll inform you as soon as possible. We will work with you to reschedule your tour when possible or provide a full refund

Is there a dress code to join this Toledo City and Winery tour?

While there is no specific dress code, we recommend wearing comfortable, casual, and respectful clothing

How much walking is involved in this tour?

This tour includes walking around Toledo and through a vineyard. While the pace is gentle, you will have to navigate uneven terrain and narrow passages

Is lunch or dinner included in the price of the tour?

As a light snack, various tapas will be served with your wine tasting. You'll also have time for a lunch of your choosing in Toledo

What if I have food allergies, intolerances, or other dietary requirements?

Please contact us in advance so we can do our best to accommodate your needs. We will work with our tour partners to provide you with an alternative when possible

Are drinks included in the price of the tour?

Yes! Wine tasting of 3 different varieties are included in the price of this Toledo City and Winery tour. However, any additional drinks are not included in the price of the tour

Can I bring my kids?

Yes, everyone is welcome on our Toledo City and Winery tour. Infants 0-4 years old are free, and we offer a reduced rate for children 4-8 years old. Please choose accordingly when booking

Does this tour include hotel pickup?

No, hotel pickup is not included on this tour. Please meet your guide at the Plaza de San Miguel in Madrid 15 minutes before departure time

Start From: $112.99

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$112.99 / per person
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