An Overnight Journey from Madrid

Destination
Madrid, Spain
Duration
36 hours
Tour size
Max 10
Language
English
Most people try to cram Toledo, Segovia, and Ávila into one frantic day trip, and end up with a selfie at the aqueduct and not much else. This Madrid to Toledo tour gives the three cities two days instead, with a night inside Toledo's walls so you're there after the buses leave and the streets go quiet.
You'll leave Madrid by private minibus and head south into Castilla-La Mancha, where the plains open out under a huge sky. Your first stop is a 16th-century windmill, the kind that inspired Cervantes, and you'll step inside to see how it worked and why a broke, idealistic knight decided to fight it. It's the moment the novel and the landscape line up.
Next is Bodegas Martúe, a family winery holding a Pago designation shared by only 13 estates in Spain. You'll taste the estate wines, bolder and more modern than the region's reputation, then sit down in the vineyard for a long lunch of homemade regional dishes. This is a proper countryside meal, not a few crackers beside a barrel.
"People always try to do all three cities in one day. It doesn't work. The whole reason we built the Overnight was to give Toledo its evening back."
Kate,
WalksDevour Overnights designer
"My favorite moment is after the day buses leave Toledo. The stone goes gold, the streets empty, and the guests realize they've got the city to themselves."
Elena,
WalksDevour Madrid guide

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