Madrid
Day trip to Toledo - the ancient ‘city of three cultures’
Day Trips & Local Escapes • 8 hours
5.0
(6)
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 this experience
Paul
Apr 2025
Marjorie
Jun 2025
Lots of great details about the history about the city. Knowledgable and pleasant tour guide, who was very easy to understand. Very much enjoyed our time on the tour.
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Rachael
Jun 2025
Lisa was lovely. Lisa was very communicative over WhatsApp before our tour. The tour was for myself and my young teenage daughter. She met us in our hotel lobby could not have been easier. We were both extremely jetlagged. Lisa took that in stride. Wish we had more time in Madrid, I would book Lisa again when we were feeling better. She will cater to whatever you would like, knew how to take the perfect picture new the secret spots and was very lovely to be around. She told us to WhatsApp her with any questions we had while in town she will be lovely with your teen’s. Kids are even if you’re an older couple all around great guide couldn’t recommend more.
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Laure
Jun 2025
Good overview of the city center of the history of Madrid. Guide was very knowledgeable. Totally recommend!
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Mark
Jun 2025
Marina gave us a great tour of Madrid highlights. She was very knowledgeable and tailored our experience to our interests. Thanks Marina!
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Dencil
May 2025
Best tour guide (Lisa) by far in Madrid. Worth doing it on first day after arrival instead of towards the end!
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