Day Trip to Toledo - the Ancient ‘City of Three Cultures’

Fairytale turrets, El Greco art and a feast at Mercado San Agustin.

  • Private &

  • 8 hours

  • From
    €119.17  EUR per person based on 2 adults

  • Walking

  • Public transport

  • Multiple languages available (including English)

What you’ll do

You’ll join one of our local Madrid hosts and go back in time 2000 years in our time machine… oh wait sorry, false alarm, you’ll just take the train. You’ll visit the ancient city of Toledo, which is so historic it feels a lot like going back in time.

A UNESCO World Heritage Site, this enchanting enclave was once known as the ‘City of Three Cultures’ thanks to the Christian, Arab and Jewish communities who all lived here, and you can still experience the city’s rich cultural tapestry today.

Wander winding cobbled streets punctuated by whimsical turrets, medieval architecture and El Greco art and feel like you’re in your very own fairytale. Visit the old Jewish Quarter and the El Transito Synagogue and Museum and see the old city walls and the 9th century Puerta de Bisagra, the imposing stone gate which once guarded the entrance to the city when it was under Moorish rule.

When lunch calls, as we find it always does, head to the Mercado San Agustin, a five-story market of gastronomic bliss where you can feast on tapas, indulge at a restaurant or nibble on regional produce as you wander. Delicious, you won’t want to leave.

Experience highlights

  • Take the train with your host who will organize tickets from Madrid to Toledo - no one likes figuring out train timetables whilst on holiday

  • Explore this historic fairytale city which is nearly 2000 years old and is a UNESCO World Heritage Site

  • Discover its most iconic landmarks like the gothic Cathedral, the El Transito Synagogue, and the 9th-century Moorish city walls

  • Wander through its historic streets, soaking up its history and charm

  • Enjoy an authentic tapas lunch at a traditional eatery recommended by your host or visit the incredible Mercado San Agustin where you can sample delicious regional produce and local wines, maybe buying some treats to take back to Madrid (one for the

Good to know

What’s included

  • 100% Private and personalized experience
  • 8 hours with a host who knows the area inside out
  • 3-4 tastings of local specialty tapas (yum!)
  • A glass of wine or soft drink and coffee
  • Train transport to and from Toledo
  • Walking experience ( other transport can be arranged at an additional cost)

What’s not included

  • Additional food and drink
  • Additional transport costs
  • Gratuities

Meet-up point

  • Your hotel/apartment or any other central location

Cancellation policy

  • Cancel 14 days before the experience for a full refund

How it works

  • Tell us your preferences and book

    See an experience you like and book it. We will ask a few questions to build the right experience with you.

  • Just right for you

    We’ll pair you with the right host based on your personality and interests. Trust us, we know all our hosts personally.

  • The fun bit

    Spend time in the city with your carefullyselected host. You have an itinerary but it’s unscripted so it’s up to you and your host where you go and what you do.

Hello curious traveler! If you’re unsure about what experience to book or would like more information on how it all works, just email me with any questions or plans you may have. I or someone from our Customer Experience Team will get in touch so we can suggest the perfect personalized experience for you.

If you prefer to speak to someone, feel free to send us your WhatsApp or cell number and we’ll give you a call back.

Reviews for Madrid


July 2019

Uma Visão Geral de Madri

Minha experiência começou alguns dias antes da data marcada para o tour, sendo que Nicola, que foi responsável por me guiar no tour, me enviou emails me explicando em detalhes como iriamos nos encontrar, e uma sugestão de intinerário. Na hora marcada, começamos o passeio por Madri. Tive a oportunidade de conhecer vários detalhes históricos dos principais edifícios e ruas da cidade. Além disso, Nicola me levou a dois mercados para que eu pudesse experimentar um pouco da culinária local... o sanduiche ramón é imperdível, como também as croquetas!!! Para finalizar, uma passada por alguns dos museus da cidade, com destaque para o Museu do Prado. Bem, foi um dia agradabilíssimo, com o encontro de mais um amigo. se recomendo, claro, com certeza!

Review by Francisco L


May 2019

3 Hour Foodie Tour of Madrid- Eat where the locals eat

Joanna was our guide and she was fantastic! My son and I found her so easy to get along with. She was very friendly, knowledgeable of the history of the various barrios we walked through, and she turned us on to some some fantastic food and drink treats. Her organization, CityUnscripted, has a real gem of a person/tour guide in Joanna.

Review by Glenn C


May 2019

Extraordinary Day in Madrid with Silvia!

Wondering typical neighborhoods, sipping coffee in a local shop, discussing the joys and challenges of today's Spain, sharing life experiences over delicious food in an authentic Spanish restaurant - these were all part of our amazing day with Silvia. Through Silvia we learned so much about life in Spain and its people, one of our primary motivations for travel. This was our first experience with CityUnscripted and it was much more like meeting up with a friend of a friend instead of a tour guide. We signed up for an 8-hour day which I thought may be too long. But the day flew by as we wandered, ducked into neighborhood stores and churches, watched children running through parks, and got to know Silvia, an innovative entrepreneur and journalist with a insatiable curiosity about everything around her and a perpetual twinkle in her eye, and her life. We also did some touristy things but saw them through the eyes of a local. Now back home, when we think of Madrid we do think of the Prado and the Palace and the churros. But we especially think of Silvia and how she lovingly shared with us the city she knows and loves. We will definitely seek out other experiences with CityUnscripted in our future travels. Highly recommended!

Review by Joy N

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