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
Julia,
Jan 2025
Lisa was fantastic-very flexible and accommodating; she adjusted the itinerary on the fly and customized the experience according to our interests. All in all, a wonderful day in Madrid!
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Ann,
Dec 2024
Spending this time with Lisa as our guide through the neighborhoods of Madrid was fantastic! We loved the opportunity to customize where we went and what we saw all throughout the day! We learned about the history and culture of Madrid, as well as stopped at some local spots to see shops and cafes that had an interesting history. Exploring with Lisa was like spending time with a friend. She was informative and funny, checking if we were enjoying our time, and giving us a perspective to what it is like to live in Madrid. We also loved hearing her stories about her journey to Madrid from Venezuela and the US, and we are so impressed with her entrepreneurial spirit of starting her own company. Fantastic day! Highly recommend! Thank you Lisa for highlighting the wonderful city of Madrid for our family!
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Kim,
Dec 2024
Let me tell you about the incredible time I had with my tour guide, Lisa, in Madrid! From the very moment we met, it was like reconnecting with an old friend who was very knowledgeable about this amazing city. Lisa was a lot of fun and brought the energy I was looking for in a guide. I wanted a flexible agenda for our 6 hours together since I was only in Madrid for part of a day. The tour was a masterclass in personalization. It wasn’t about a script or a schedule—it was about me. What I wanted to see, feel, and experience. And somehow, Lisa just knew exactly how to craft the perfect day. We had an amazing connection and by the end, I wasn’t just saying goodbye to a guide—I was saying goodbye to a new friend. If you’re thinking about exploring Madrid, Lisa is the guide you need.
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Danny,
Dec 2024
Lisa took us on a historic old town tour. We enjoyed our 2 hour walking tour and found the history provided by Lisa created a great picture of old town Madrid through the centuries. Thank you Lisa!
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Alina,
Nov 2024
It was a nice experience, on our fist day to Madrid. Really enjoyed our private tour. Lisa was great, highly recommended her tours!
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Abigail,
Nov 2024
The tour was great, Lisa has a lot of knowledge about the city and its history, and shared information which I would not have known if I had gone on my own. She was friendly and helpful too, and walked me to the Prado museum as she wanted to make sure I reached there safely, even though our tour had ended Definitely engage her for walking tours!
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