Tours in Tuscany

Chianti Castle wine tour, San Gimignano and Siena

Tuscany Wine Tours

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Embark on a Unique and Authentic Journey Through the Enchanting Tuscan Countryside

We will explore a scenic and authentic part of the Chianti region—still untouched by mass tourism.

Let us guide you on a truly unforgettable experience through the breathtaking landscapes of the Tuscan countryside, surrounded by rolling hills dotted with olive trees, vineyards, and cypress trees.

Our journey will lead us to a stunning, authentic Medieval tuscan castle—one of the few in the region that still allows guided tours inside. Here, you'll be immersed in the Renaissance atmosphere as you explore the beautifully preserved interior, wander through the gardens, and climb the ancient tower to admire a spectacular view.

The tour continues with a visit to the castle’s historic wine cellars and the “Vinsantaia”—where the prized and traditional Vin Santo, made from Malvasia grapes, slowly matures in ancient chestnut and oak barrels after the grapes have dried on racks.

After the visit, you’ll enjoy a wine tasting paired with a light Tuscan lunch of crostini, local cured meats, cheeses, and typical regional delicacies. To finish, you’ll sweeten your palate with traditional Tuscan biscuits dipped in Vin Santo—a beloved local custom.

After lunch,  we will arrive at the UNESCO World Heritage site of San Gimignano, celebrated for its original medieval towers. Stroll through the historic city, where each step reveals tales of a bygone era. Capture the essence of this unique destination, where history and architectural marvels coalesce seamlessly. In San Gimignano you can taste the world champion ice cream “Dondoli”.

After we will drive you to Siena, a jewel in the heart of Tuscany, is renowned for its iconic "Piazza del Campo" and medieval charm. The city's narrow streets, vibrant markets, and stunning Cathedral of Santa Maria Assunta create an enchanting atmosphere. Siena invites you to immerse yourself in its rich history, art, and authentic Italian.

Our drivers know a lot about the places they take you to. They can offer insightful explanations about the history and local traditions of the areas you'll explore. However, in adherence to Italian law, your driver is unable to leave the vehicle unattended, accompany you, or enter museums or other sights with you.

GENERAL INFORMATION

  • Available: All year round. Rain or shine - from monday to friday 
  • Duration: 10 hours

 

INCLUDED IN THE TOUR

  • Luxury air conditioned vehicle
  • Pick up and drop off at your accommodation
  • English speaking Driver  for the day at disposal
  • All local Taxes, gasoline, driver's meal
  • wine tour and light lunch at Castle in Chianti 

 

NOT INCLUDED

  • Anything not mentioned in the program

 


Q&A




  • Question: What makes this Exclusive Chianti Castle visit with wine tasting + San Gimignano & Siena one of the best chianti wine tours from florence?

    Answer: It’s a complete chianti day tour from florence that combines an authentic chianti castle experience with curated chianti wine tasting, plus the iconic medieval atmosphere of san gimignano and the timeless beauty of chianti siena. You get countryside scenery, history, and top-quality tastings in one seamless day—ideal if you’re looking for the best chianti wine tour without wasting time on logistics.



  • Question: Is this a true chianti castle tour, and what happens at the chianti castle winery?

    Answer: Yes—this is a real chianti castle tour where you visit a working chianti castle winery in the heart of chianti classico. You’ll enjoy guided tastings focused on best chianti wine styles, learn about local production, and experience the atmosphere that makes chianti castles so special—historic walls, vineyard views, and an authentic Tuscan setting.



  • Question: I’m staying in Florence—can I do a chianti afternoon wine tour from florence or is it a full chianti tour from florence?

    Answer: This itinerary is designed as a full chianti tour from florence so you can include the chianti and san gimignano guided tour experience and still reach Siena comfortably. If you only have limited time, we can also structure it like a chianti half day wine tour focused on the castle and tastings—perfect if your priority is a chianti wine tasting tour from florence with maximum quality in fewer hours.



  • Question: Why combine chianti san gimignano and Siena in one day—what’s the benefit versus separate day trips?

    Answer: Pairing chianti to san gimignano and Siena creates a balanced day: vineyards and tastings first, then two of Tuscany’s most famous medieval towns. It’s one of the smartest chianti day tours because you get a true chianti tuscany wine tour feel, plus landmark sights and free time to explore—ideal for travelers searching chianti and san gimignano guided tour options that don’t feel rushed.



  • Question: Can this be a private chianti wine tour with a driver, and is it suitable for families or travelers who want flexibility?

    Answer: Absolutely—this can be a chianti wine tour private experience with chianti drivers private tours style service, meaning flexible timing, photo stops on the countryside roads, and an itinerary adapted to your pace. It also works well as a chianti wine tour with kids because we can adjust breaks, walking time, and the balance between tastings and sightseeing in san gimignano and Siena.


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