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Chianti Charm: Siena to Florence via Tuscany’s Wine Country
Historic villages, vineyard views & fine wines in the heart of Chianti

Chianti Charm: Siena to Florence via Tuscany’s Wine Country

Embark on a captivating transfer from the medieval charm of Siena to the Renaissance splendor of Florence, with two enchanting stops in the heart of the Chianti region. This journey offers scenic drives, historic exploration, and the renowned flavors of Tuscany's most famous wine country. Along the way, you'll visit one charming medieval village and sample local wines in a renowned vineyard nestled among rolling hills and cypress-lined roads.

Wine Tasting and Lunch at Castello di Fonterutoli
Your driver will guide you to Castello di Fonterutoli, a historic wine estate where tradition meets elegance. Enjoy a guided tour of the cellars and learn about the centuries-old tradition of Chianti wine production. Your visit will culminate in a commented wine tasting session, where you will sample a variety of Chianti wines, including the prestigious Chianti Classico and Riserva. Your hosts will guide you through each tasting, helping you appreciate the unique characteristics of these world-famous wines.

Following the wine tasting, you will enjoy a traditional Tuscan lunch overlooking the vineyards. This meal, included in your tour, will feature authentic local cuisine prepared with fresh, seasonal ingredients paired with signature wines.

Afternoon in a Charming Chianti Town
After lunch, you'll journey through the rolling hills, vineyards, and olive groves that characterize the Chianti region. You'll get the chance to choose your destination from some of the most picturesque villages of Chianti. You will have time to visit one rustic town so you might opt to visit Greve in Chianti, known for its unique triangular piazza, or Castellina in Chianti, which has an imposing fortress and panoramic views. Alternatively, you could explore Radda in Chianti, a town encircled by massive stone walls offering stunning vistas of the surrounding countryside. 

Whichever village you choose to visit, you will have free time to stroll through charming streets, admire historic churches, and browse artisan shops offering a taste of authentic local life. Each town offers fine wines, panoramic views, and unique glimpse into the authentic Tuscan way of life, far from the tourist crowds.

Scenic Drive to Florence
Settle back into your comfortable vehicle for the final leg of your journey to Florence. As you travel, you will be treated to more stunning views of the Chianti landscape. Your driver will be happy to make photo stops along the way, allowing you to capture the beauty of the Tuscan countryside.

You will arrive in Florence by 5 PM, enriched by the flavors, scenery, and soul of Chianti, and your driver will drop you off at your hotel.

Tour Information

  • Tour Code : SIEFLO01.25
  • Type : Private Tour
  • Category : Art & History
  • Duration : 6 Hours
  • Departure City : Siena, Italy
  • Ending City : Florence, Italy
  • Departure : Guaranteed Departure
  • Grade/Difficulity : Moderate
  • Transport Mode : Walking + 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: 11:00 AM
  • Starting/Meeting Point : Your hotel
Availability
From January 2025 To December 2025
English - Every Weekday
Blackout Dates
25 December 2025
Highlights
  •  Tour the cellars at Castello di Fonterutoli and taste award-winning Chianti wines guided by expert hosts.
  •  Savor a traditional multi-course meal made from fresh, regional ingredients in a stunning vineyard setting.
  •  Choose to visit either Greve in Chianti, Castellina in Chianti or Radda in Chianti.
  •  Enjoy panoramic drives and photo stops through one of Italy’s most iconic landscapes.
Tour Includes
  •  Private Driver Escort
  •  Pickup from your hotel in Siena
  •  Guided winery tour and tasting of 4 wines at Fonterutoli
  •  4-course Tuscan lunch paired with wine at Fonterutoli
  •  Visit one Chianti village and enjoy free time for exploration
  •  Drop off at your hotel in Florence
Tour Excludes
  •  Expert Local Guide
  •  Personal expenses
  •  Any items not specifically mentioned in the inclusions
Notes
  •  Winery included in the tour may be substituted with a similar one according to availability.

Pricing

FromToPax 1Pax 2Pax 3Pax 4Pax 5Pax 6
Jan 2, 2025 Dec 31, 2025 € 858 € 473 € 345 € 281 € 242 € 217
Monday,Tuesday,Wednesday,Thursday,Friday,Saturday,Sunday
* Price Per Pax