Chianti Private Wine Tour from Florence

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

Tour Overview

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.

Best for
Chianti Classico, Sangiovese, Tuscan cooking and medieval villages
Tour style
Full-day private wine tour
Suggested duration
One day from Florence or Siena

Signature journey

Signature Chianti Wine Tour Itinerary

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

  1. Day 1Florence - Chianti Classico - Florence

    Felsina winery

    Private Chianti Wine Tour

    Felsina winery

    • None
    • Lunch with wines
    • Private Chauffeured Mercedes

    Morning: You can begin this tour in Florence. Your private chauffeur will collect you from your hotel, and you will enjoy a very scenic drive through the delightful Tuscan wine country. Your first winery appointment will be one of the prestigious producers in the whole Chianti Classico region, including Castello di Volpaia or Fontodi. The visit is arranged privately for your party, and the family owners will greet you. 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 chauffeur-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. Dishes in this meal include fettunta, bruschette, and other seasonal Tuscan antipasti, pappardelle al ragù di Lepre (long, flat pasta with wild hare), rosticciana alla griglia (grilled pork ribs), and various regional specialties. Lunch is accompanied by a selection of regional wines, which includes Chianti Classico Gran Selezione. 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 walled 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. Also, we suggest you take in the fantastic walled village of Monteriggioni, a gorgeous little town, another “must-see.” Your chauffeur-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.

What's Included?

Hotel pickup and return in a privately chauffeured Mercedes

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

Read our private wine tour planning guide

Frequently Asked Questions

What is included in a private wine tour?

This private day tour includes transportation with a chauffeur-guide, two pre-arranged winery appointments and tastings, a leisurely Tuscan lunch with regional wines, itinerary planning and support from Cellar Tours.

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?

All itineraries are private and pre-arranged for your party.

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 Access wineries, traditions, and places not open to all.

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