from
$133
Half-Day Toledo City Tour with Winery Visit from Madrid
From Madrid, explore the City of Three Cultures alongside an expert guide and sample 3 select wines
What's included
Passionate English-speaking guide
Roundtrip transportation
Wine tasting
Toledo
Winery visit
Group size of max 30 people
Guide gratuities
Hotel pick-up and drop-off
Food and beverages
Itinerary
Meeting Point is at Plaza San Miguel, 7. Madrid
After meeting your expert guide and fun group of fellow travelers in the heart of Madrid, hop into your comfortable vehicle for the day!
Mirador del Valle
Take in unparalleled, panoramic views of Toledo as your guide explains more about the historic city’s fascinating past
Plaza Zocodover
Wander through Toledo’s central hub, a lively square which is brimming with vibrant restaurants, bars, and shops
Jewish quarter
Explore the winding streets of Toledo’s Jewish Quarter, which are lined by local shops and historic synagogues
Cathedral of Toledo
Visit the second largest cathedral in Spain, renowned for its intricate, Gothic-style altar and spectacular facade
Winery visit
Drive to a stunning winery in the Spanish countryside, where you’ll enjoy a tasting of three local wines and perfectly paired tapas
Vineyards
Before sipping on the estate’s delicious wines, stroll through the winery’s enchanting vineyards and visit their delightful wine cellar
Learn from a sommelier!
Listen closely as an expert sommelier spills the secrets of how Toledo’s wine is made, and learn about the unique flavors of this region
Finish your tour at calle Bailén, 25
After a scenic drive back to Madrid, you’ll be dropped off in the city center, just in time to experience the city by night!
For Reference Only. Itineraries are subject to change
Select participants and date
Start times are in the product’s local time
Free cancellation up to 24 hours in advance!
Mon, 07 Sep 2026
Meeting and drop-off point
Important Details
Your memorable half-day trip begins in the morning in the centre of Madrid, where you’ll meet your group at Plaza de San Miguel, 7 and hop into a comfortable mini-van bound for Toledo. Upon arrival, learn about the balance of Christian, Muslim, and Jewish influences during a guided walking tour through the Jewish Quarter and to the Cathedral of Toledo.
After free time in Toledo to explore independently, your trip continues with a transfer to a scenic winery tucked in the surrounding rolling hills. Here, an expert sommelier will reveal the region's secrets while leading you through the vineyard and into the cellar for a tasting. Unfortunately, all good things must end, and early in the afternoon, you'll settle in for the hour's transfer back to Madrid.
Half-Day Toledo City Tour with Winery Visit Description
Your 8-hour tour includes:
Guided tour of Toledo with an official guide
Free time to explore Toledo
Visit to a family-run winery in the Toledo Region
Vineyard walk and wine-making insights
Wine tasting of 3 select wines with tapas pairing
Comfortable round-trip transportation from Madrid in a luxury mini-van
Small group experience for a more personalized tour
Departing From Madrid
Your adventure begins in Madrid’s Plaza de San Miguel, where you’ll meet your official expert guide and board a comfortable luxury mini-van along with a few other like-minded travelers. Soon, you’ll be making your way out of the lively city, alongside olive groves, and through quaint towns to the hilltop town of Toledo. Known as the "City of Three Cultures," you’ll immediately swept away by Toledo’s impressive yet diverse architecture, which has been influenced by Christian, Muslim, and Jewish residents.
Explore Toledo
Your time in Toledo starts with a guided walk led by an official expert. Thanks to their local knowledge, you'll be let in on the city's fascinating stories as you meander through the Jewish Quarter's winding streets dotted with synagogues and quaint shops. You'll also be led to the magnificent Toledo Cathedral, a masterpiece of Gothic architecture.
After the guided tour, you'll have time to explore Toledo on your own. Wander through the labyrinthine streets, grab lunch at one of the local taverns offering delectable Spanish dishes, or perhaps find a cozy café to sample Toledo’s famous marzipan. Just keep an eye on your watch, as it’s time to bid well to Toledo.
A Taste of Toledo’s wines
Back in the van, your journey continues through rolling hills to a traditional winery. Here, you’ll meet an expert sommelier who’ll teach you the secrets of Toledo wines as you stroll through a vineyard and head inside a charming wine cellar. Surrounded by aging wine, you’ll sample three different varities, each chosen for its unique flavors that are characteristic of the region. Along with the wine, delight in perfectly paired bites and tapas.
As evening approaches, it’s time for your return to Madrid. Board the comfortable mini-van once again and settle in for an hour's ride, and before you know it, you’ll be back to Calle Bailén, 25, right next to where your adventure all started. Yet, with this carefully curated trip, you’ll be carrying with you many memorable moments and photos to go along with them.