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
Bill
Apr 2025
Patricia did a fantastic job. We enjoyed the tour. She was communicative ahead of time and easy to work with. It was an extremely informative tour. She was very knowledgeable about the city.
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Donald
Apr 2025
Lisa was warm, upbeat and easy to be with. It felt like we were touring the city with a friend of a friend, she tailored the experience for our enjoyment.
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Quentin
Apr 2025
Lisa was a wonderful host and a great person with whom to spend time.
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Paul
Apr 2025
We had a great tour with Lisa. She was a knowledgeable and helpful guide. We all enjoyed seeing the city and spending time with her.
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Traci
Apr 2025
We had scheduled a small group tour but at the last minute we decided we really wanted a private one-on-one experience to truly learn about Madrid. We are so glad we did and that Patricia was our guide. She had so much knowledge and was filled with fun facts that you only get with a true local. With a bubbly personality and lots of information, we learned so much. She also introduced us to the oldest cocktail bar in Madrid and the Lhardy (the first true restaurant in the world with menus, proper service, etc) and we were lucky enough to dine there the next evening. Her knowledge on the Spanish civil war was exceptional too. Definitely book this early on your trip while in Madrid. You will walk away with a list of places to come back to - ways to navigate the city and a better appreciation for beautiful city of Madrid.
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