Chianti Classico Private Wine Tour from Florence

Private winery appointments, a leisurely Tuscan lunch and a hill town in the heart of Chianti Classico.

Chianti Classico
Monteriggioni
Radda In Chianti
Sangiovese
Tuscany

Private Chianti Classico Wine Tour from Florence

Introducing Our Private Chianti Classico Wine Tour from Florence

This full-day private Chianti Classico tour begins at your Florence or Siena hotel and includes two privately arranged winery visits, a leisurely Tuscan lunch with regional wines, private Mercedes transport with a driver-guide, and time in a hill town selected to suit the day’s route.

The ancient wine country of Chianti is a “must-do” for wine lovers. Chianti Classico lies between Florence and Siena, in a familiar Tuscan landscape of castles, hilltop villages and vine-covered valleys. Its finest wines are Sangiovese-led reds, ranging from the freshness of Chianti Classico Annata to the greater depth and maturity of Riserva and Gran Selezione. Many estates have occupied the same land for centuries, with atmospheric cellars, vaulted barrel rooms and tasting rooms overlooking the vineyards.

This itinerary draws on Cellar Tours’ first-hand experience arranging private wine travel in Tuscany. Our team selects the estates, route and lunch around your wine interests, travel dates and preferred pace.

Best for: Chianti Classico, Sangiovese, Tuscan cooking and medieval villages
Tour style: Full-day private wine tour
Suggested duration: Approximately 8 hours from Florence or Siena
Price & availability: Pricing is tailored to your travel dates and party size. Inquire for confirmed availability and a complete quote.

As featured in

View our press coverage

Signature journey

Sample Private Chianti Classico Wine Tour Itinerary

Highlights include a private day through Chianti Classico with your driver-guide, two pre-arranged winery visits, a leisurely Tuscan lunch and time in a hill town selected to suit the day’s route.

Day 1Florence - Chianti Classico - Florence

Private Chianti Classico Wine Tour Itinerary
Felsina winery
- No Overnight Stay
- Lunch with wines
- Private Mercedes with Driver-Guide
Morning: Start your tour in Florence. Your private driver-guide will collect you from your hotel, and you will enjoy a scenic drive through the delightful Tuscan wine country. Your first winery appointment will be with one of the prestigious producers in the Chianti Classico region, including Castello di Volpaia or Fontodi. The visit is arranged privately for your party, with the estate team hosting your visit and tasting. You will begin in the vineyards and receive an explanation of the terroir- the combination of local climate, soils, and grape varieties that are the components that make wines so unique from region to region. A tasting of their prestigious wines will follow.

Lunch: After all this hard work, you will be ready for lunch. Your driver-guide will take you to a fantastic local Trattoria for a leisurely Tuscan lunch, beginning with a glass of Vernaccia di San Gimignano as an aperitif. A typical lunch might include fettunta, bruschetta and seasonal Tuscan antipasti, followed by handmade pasta or a traditional meat dish and other regional specialties. Lunch is paired with a selection of regional wines, chosen to complement the menu. To finish, enjoy cantucci served with Vin Santo.

Afternoon: After lunch, continue to a second distinguished Chianti Classico estate. Depending on the route and timings, this may be Fèlsina or San Giusto a Rentennano. You will enjoy a walk through the vines and a full tour of the vinification rooms and barrel chambers, followed by a superb tasting of wines. We have a special treat for olive oil lovers: a guided tasting of the estate’s virgin olive oils.

Late Afternoon: If time permits, you can take a short detour to a charming Tuscan village before returning to your hotel. If staying in Florence, you can visit the medieval hill town of Radda in Chianti on your return journey. Radda is lovely and has plenty of gourmet shops, should you want to pick up some nice bottles or decanters on your gourmet day out. We also suggest you take in the fantastic walled village of Monteriggioni, a gorgeous little town. Your driver-guide will show you around the town, and you can relax at a wine bar, go gourmet shopping, or enjoy the atmosphere.

Return transfer to Florence or Siena.

Personal planning

Meet Your Tour Planner

Simona Piccinelli Sales Director

Born in Brescia, in the heart of Franciacorta wine country, Simona brings first-hand knowledge of Italy and its wine culture to every journey she plans. She regularly travels through Italy’s wine regions, visiting wineries and hotels, meeting local guides and restaurant partners, scouting new destinations and experiences, and reviewing feedback from Cellar Tours guests. Fluent in Italian, English and French, Simona uses her local knowledge and wine-industry experience to help travelers choose the region, itinerary style and pace that best match their interests.

What's Included?

Hotel pickup and return in a private Mercedes with your driver-guide
Two pre-arranged Chianti Classico winery visits and tastings
A leisurely Tuscan lunch with regional wines
Route and appointment planning based on your wine interests
Support from Cellar Tours before and during the tour

Frequently Asked Questions

How far is Chianti from Florence, and is it suitable for a day trip?

Chianti Classico lies between Florence and Siena and is particularly well suited to a private day trip from Florence. We plan the route as a full-day itinerary, allowing time for two winery visits, a leisurely Tuscan lunch and, where timings permit, a stop in one of the region's hill towns.

How many wineries can we visit in one day?

This itinerary includes two pre-arranged Chianti Classico winery visits and tastings. We find that two estates allow enough time to enjoy the visits properly, have a relaxed lunch and travel through the countryside without rushing the day.

Does the Chianti wine tour include hotel pickup in Florence?

Yes. Your private driver-guide collects you from your Florence hotel and returns you there at the end of the day in a private Mercedes. The itinerary can also begin in Siena.

Can the Chianti itinerary be tailored to particular wineries or wine interests?

Yes. We select the estates, route and lunch around your wine interests, travel dates and preferred pace, with the final arrangements confirmed in your personal proposal.

Can the tour begin in Siena?

Yes. Although this itinerary is particularly convenient from Florence, it can also be adapted for guests staying in Siena or elsewhere in the Chianti countryside.

Are the winery visits private?

Yes. Winery visits and tastings are privately arranged in advance for your party and confirmed in your personal proposal.

Can the itinerary be adjusted for mobility or dietary needs?

Yes. Share mobility considerations, allergies, dietary preferences and pacing needs early so that we can adapt the transport, restaurants and visits wherever possible.

Trusted local partners Handpicked for quality and authenticity.
Flexible by design Itineraries tailored to your interests.
Support every step Before, during, and after your journey.
Authentic experiences Privately arranged winery visits and local experiences selected around your interests.