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Premium Chianti Classico: Vineyards, Villages & the Art of Fine Winemaking
Discover the heart of Chianti through its historic towns and renowned wineries

Premium Chianti Classico: Vineyards, Villages & the Art of Fine Winemaking

Begin a fascinating journey through the heart of Chianti, where vine-covered hills reveal the story of centuries-old winemaking traditions. This full-day tour guides you from the historic Fattoria di Vignamaggio to the picturesque towns of Radda and Greve, concluding with a visit to the esteemed Castello di Fonterutoli.

Morning: Discover the Rustic Charm of Greve in Chianti

Your Chianti adventure begins as your private driver collects you from your accomodation and whisks you away to the charming town of Greve in Chianti. Often considered the gateway to Chianti Classico, Greve is surround by rolling vineyards and olive groves. You'll have free time to visit the town’s triangular main square, lined with porticos and artisan boutiques. Discover the Santa Croce Church and  local museums or spend your time exploring the local shops selling a variety traditional Tuscan products, from hand-crafted ceramics to aromatic cheeses and salumi. 

Wine tasting and lunch at Fattoria di Vignamaggio – A Legacy of Excellence​
Next, you'll make your way to the illustrious Fattoria di Vignamaggio, an avant-garde, organic farm and wine cellar more than 600 years old. Immerse yourself in the vineyards, olive groves, vegetable gardens, and luxuriant fruit orchards that cover more than 400 hectares of the Chianti Classico heartland. Not far from the Fattoria, Villa Vignamaggio stands out with a history dating back to the 14th century: it is said to be the birthplace of Lisa Gherardini, better known as the Mona Lisa, Leonardo da Vinci's most famous subject.

Your guided tour of the estate will take you through its cellars and vineyards, where you will learn about the evolution of winemaking techniques from the Renaissance to the present day and how Vignamaggio balances respect for tradition with modern innovation.

The experience culminates in a tasting of Vignamaggio's exceptional wines. From classic Chianti Classico to innovative Super Tuscans, each wine tells a story of the estate's terroir and heritage. Your host will guide you through the tasting, providing historical context and helping you appreciate the complex flavors that centuries of expertise have crafted.

Following the tasting, savor a gourmet lunch at the estate's restaurant. Here, innovative Tuscan cuisine is paired perfectly with Vignamaggio wines, offering a complete sensory experience that celebrates the region's culinary heritage.

Early Afternoon: Exploring Radda in Chianti
After lunch, your journey continues to the heart of Chianti Classico. You'll visit the enchanting town of Radda in Chianti, once the capital of the Chianti League. Use you leisure time to wander through its narrow, medieval streets and take in the stunning views of the surrounding valleys from the town's strategic hilltop position.

Late Afternoon: Castello di Fontrerutoli

Your final destination is the renowned Castello di Fonterutoli. Owned by the Mazzei family for 24 generations, this estate embodies the very essence of Chianti's winemaking heritage.

As you approach, marvel at the picturesque hamlet of Fonterutoli, its stone buildings a testament to centuries past. Your expert guide will lead you through the state-of-the-art winery, blending modern technology with time-honored traditions. You will learn about the Mazzei family's pivotal role in Chianti's history, including their contribution to the original formula for Chianti wine in 1398.

Explore the extensive cellars carved deep into the hillside, where thousands of barrels of wine slowly mature in perfect conditions. Your tour culminates in a tasting of Fonterutoli's exceptional wines, including their acclaimed Chianti Classico and perhaps their top cuvée, Siepi. Each sip tells a story of terroir, tradition, and the family's unwavering commitment to quality.

As the sun begins to set over the Chianti hills, your driver will escort you back to your accomodation.

Tour Information

  • Tour Code : MONTE503.25PREM
  • Type : Private Tour
  • Category : Food & Wine Tours
  • Duration : 9 Hours
  • Departure City : Montepulciano, Italy
  • Departure : Guaranteed Departure
  • Grade/Difficulity : Easy To Moderate
  • Transport Mode : Car/Minivan
  • Children Allowed : Yes
  • Min Group Size : 1
  • Max Group Size : 6
  • Arrangement : Driver-Escort
  • Entrance Fee : No inside visits
  • Hotel Pickup : Yes
  • Language Offered : English
  • Hotel Dropoff : Yes
  • Meeting Time: 08:30 AM
  • Starting/Meeting Point : Your hotel
Availability
From March 2025 To November 2025
English - Every Weekday Except Wednesday
Highlights
  •  Dive into the legacy of centuries of winemaking in the Chianti region and discover how tradition and innovation shape every vintage.
  •  Savor a gourmet lunch paired with exceptional wines at Fattoria di Vignamaggio, a cornerstone of Chianti winemaking.
  •  Wander through lush vineyards and historic cellars as you learn how winemaking has evolved from the Renaissance to today.
  •  Soak in panoramic views, browse artisan shops, and savor the timeless charm of Radda and Greve in Chianti, two of Tuscany’s best-preserved medieval villages.
  •  Experience the legacy of 24 generations of winemaking at Castello di Fonterutoli and enjoy a guided tour and tasting of its iconic Chianti Classico wines.
Tour Includes
  •  Self-guided visit of Radda in Chianti and Greve in Chianti
  •  Wine tasting and tour at Castello di Fonterutoli
  •  Traditional lunch paired with wine
  •  Wine tasting and tour at Fattoria di Vignamaggio
  •  Private Driver Escort with pick-up and drop-off
Notes
  •  The route may change according to traffic conditions and availability of wineries or tickets.
  •  The wineries included in the tour may be substituted with others of a similar level, according to availability.

Pricing

FromToPax 1Pax 2Pax 3Pax 4Pax 5Pax 6
Mar 1, 2025 Nov 30, 2025 € 754 € 429 € 324 € 269 € 236 € 214
Monday,Tuesday,Thursday,Friday,Saturday,Sunday
* Price Per Pax