Private Tour: Toledo Night Tour Wine & Tapas from Madrid
Step beneath the surface of Toledo: myths, mysteries, and flavors await
Uncover Toledo’s secrets hidden beneath its ancient streets
Explore the Jewish Quarter, hear legends and ghost stories, and descend into Toledo’s hidden underground. A unique journey through history, ending with typical tapas and Castilla-La Mancha wine.
Highlights
Discover the Jewish Quarter and lesser-known convent areas
Hear stories of love, revenge, mysticism, and miracles
Visit underground spaces like the Inquisition prison dungeons
Learn about Toledo’s Imperial, Conventual, and 19th-century eras
End with a Castilian tapas tasting and two drinks, including local wine
What To Expect
Dare to dive deep into Toledo’s hidden soul on this unforgettable walking tour through its lesser-known streets and underground spaces. Led by an official English-speaking guide, this experience goes beyond history — it's about the legends, emotions, and mysteries that shaped the city.
We begin in the Jewish Quarter and the area of the convents, where narrow alleys whisper tales from before the Muslim conquest. As you walk through emblematic streets, your guide will share myths and stories of love and heartbreak, revenge, tragedy, and miracles, passed down through generations.
Next, venture underground — into dungeons and secret chambers that once formed part of a prison from the Inquisition. These rarely visited locations offer a powerful glimpse into Toledo’s underworld, rich in unusual and surprising details.
The walking tour is designed to help you experience three essential periods in the city’s history: the Imperial era, the Conventual era, and the transformative 19th century.
We wrap up the journey with a tasting session of regional tapas, including delicious products from Castilla-La Mancha, paired with two drinks — one of which can be a local wine. This Premium Small Group experience guarantees a personal, engaging, and delicious farewell.
Included
Air-conditioned minibus transportation
Official English-speaking guide
Entry to the Inquisition dungeons
Tasting session of Castilian tapas
Two drinks (one wine option included)
Extras
Hotel pickup or drop-off
Additional food or beverages (unless specified)
Gratuities (optional)
Cancellations
Customers will receive a full refund or credit with 48 hours notice of cancellation except entrance tickets to monuments/tourist attractions. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. No-shows will be charged the full price.