Madrid
Day trip to Toledo - the ancient ‘city of three cultures’
Day Trips & Local Escapes • 8 hours
5
(43)
Day trip to Toledo - the ancient ‘city of three cultures’
Fairytale turrets, El Greco art and a feast at Mercado San Agustin.
What makes this experience special
Key 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
What to know before you go
Here’s everything you need to know before your day unfolds.
8 hours
Fully tailored to your preferences
English Other languages may be requested
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
Meeting point
Your hotel/apartment or any other central locationCancellation
Free cancellation up to 24 hours before the experienceWhat to bring
- We recommend wearing comfortable shoes and carrying a light bag for your essentials.
- Public transport may be used during the experience - please bring a travel card or small amount of cash for fares.
How your day could unfold
A flexible, unscripted experience designed entirely around your interests. Your host will adapt the day based on what excites you mostWhat 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.
1. Select a date
2. Select start time
3. Tailor your experience
Answer a few quick questions to help your host craft the perfect day tailored to you.
1. What’s your preferred hosting style?
2. How would you like the pace of your day?
3. What’s your walking comfort level?
4. Are you celebrating something special?
Real Stories, Real Connections
See our hosts and guests creating memories
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What travelers think of our Spain experiences
Deborah
May 2025
Cloti is an excellent tour guide. She made my husband and I feel very welcomed to Seville. We had a wonderful walking tour full of interesting and unexpected bits of history and culture. We love the personal touch and being able to have a conversation instead of listening to a rote script. It was very special to be introduced to Seville this way - we highly recommend!
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Paul
Apr 2025
Cristian
Aug 2024
Excelente Me encontré con Lisa en Barajas y tomamos el Metro a la ciudad Lisa muy atenta, con un saludo genuino Fuimos a desayunar y después le dimos al recorrido de casi 5 horas a pie por el centro de Madrid Buen ritmo y me dio datos que ningún guía anteriormente Me había dado 100% recomendable Excellent I met Lisa in Barajas and we took the Metro to the city Lisa very attentive, with a genuine greeting We went to have breakfast and then we started the almost 5-hour walking tour through the center of Madrid Good pace and gave me information that no guide had previously given me 100% recommended
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Cindy
Oct 2019
My mother and I toured with Silvia on our first day in Madrid. She is very friendly, full of energy and provided us with her inside view of 3 neighborhoods (Salamanca, Malasaña and Centro). She took us off the touristy streets and it made the tour more personable. She also took us to one of her favorite lunch spots...La Pescaderia. It was delicious and very reasonable. If you’re looking for an overview of the city, I highly suggest requesting Silvia!
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Francisco
Jul 2019
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!
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Amy
Jul 2018
Joanna asked me what my favorite experiences were and then created a fabulous personalized walking adventure in Madrid. We spent eight hours seeing gardens, markets, shopping, eating, and taking pictures in all the historical districts. We walked a lot, but the conversation and historical information shared made the day be totally pleasurable. We toured multiple art museums together and her expertise in Art History was obvious. She prides herself in her guests having a great experience. Wonderful day with a wonderful person.
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