In short
Chianti Classico Wine Tour from Florence at a Glance
Our Chianti Classico wine tour from Florence is a 6-hour day, pick-up and drop-off included, in the Chianti Classico DOCG, the historic wine zone between Florence and Siena. You visit 2 organic and/or biodynamic family-run wineries, taste Chianti Classico DOCG wines (around 10 across both estates) and 2 extra virgin olive oils, and have a traditional Tuscan lunch at the winery.
The semi-private tour costs €196 per person, for a maximum of 8 guests. The private tour is for your group only, from €350 each for 2 people down to €180 per person for 8. All prices include VAT.
Out of the Box Florence is a licensed, locally owned tour operator led by Stefano Mazzantini, a FISAR-certified sommelier. We never take commissions from wineries and never stop at wine shops. Rated 5.0/5 from 180 reviews on Google (September 2026).
Tour at a glance
Chianti Classico Wine Tour: Key Facts
Duration
6 hours
Including pick-up & drop-off
Group size
Max 8 guests
Private or semi-private
Minimum age
18 years
Children welcome on private tours
Languages
English & Italian
Expert guide for the day
Pick-up
Private: Florence hotel / B&B
Semi-private: Piazza della Libertà, 50129, in front of Caffè Lietta, Florence. Also from Siena (+€150, private only)
Wineries
2 organic estates
Organic and/or biodynamic, family-run
Lunch
Included
At the organic family-run winery
Price from
€196 semi-private · €180 private
VAT included · private from €180/person (groups of 8)
Choose your option
Semi-Private or Private Chianti Wine Tour?
Both options follow the same itinerary with the same guide. The difference is who shares the day with you, where you are picked up and how flexible the timing is.
Private tours are recommended for families, couples and anyone who prefers a fully personalised experience.
Your day
How the Chianti Wine Tour Day Works
- Morning pick-up in Florence. At your hotel or B&B on the private tour, in front of Caffè Lietta in Piazza della Libertà on the semi-private tour.
- Scenic drive into Chianti Classico. Rolling hills, vineyards and olive groves, seen from our luxurious, air-conditioned minivan with leather seats.
- Two organic and/or biodynamic wineries. Small, family-run producers explain their winemaking from grape to bottle, and you often meet them in person. You taste Chianti Classico DOCG and other labels that depend on the winery and the season, around 10 wines in total, plus 2 extra virgin olive oils.
- Tuscan lunch at one of the wineries. A full traditional lunch with local, seasonal ingredients and Chianti Classico wine pairing.
- Back to Florence. The whole day lasts 6 hours, pick-up and drop-off included.
On a private tour you can add a 3rd winery and shape the day around your preferences.
Pricing
Tour Pricing: All Options
All prices VAT included. Siena departure: +€150 supplement. Prices may vary by season.
What's included
- Luxury air-conditioned transportation from/to Florence
- Expert guide for the day
- Visits to 2 organic and/or biodynamic wineries
- Chianti Classico DOCG wine tastings
- 2 extra virgin olive oil tastings
- Great Tuscan lunch at the organic family-run winery
- Scenic drives through the Chianti Classico countryside
Not included
- Personal expenses
- Siena departure supplement (approx. €150)
- Anything not listed in "What's included"
- A 3rd winery visit can be added for private groups: the day is fully customisable to your preferences
Where
Where the Tour Takes Place
Location: This tour takes place in the Chianti Classico DOCG, the historic wine zone stretching between Florence and Siena, Tuscany, Italy. Key towns in the area include Greve in Chianti, Panzano in Chianti, Radda in Chianti, and Gaiole in Chianti. The zone is approximately 40 km south of Florence and 40 km north of Siena.
Plan your day
Chianti Guides from Our Sommelier
FAQ
Frequently Asked Questions
How much does the Chianti Classico Wine Tour cost?
The semi-private tour costs €196 per person. Private tours are priced per group: €700 for 2 people (€350 each), scaling down to €180 per person for groups of 8. All prices are VAT included. A supplement of approximately €150 applies for departures from Siena.
What is the difference between semi-private and private?
The semi-private tour (€196/person) is shared with a small group of up to 8 travellers with similar interests. The private tour is reserved exclusively for your group: same itinerary, same guide, but with total flexibility on timing, pace, and stops. Private tours are recommended for families, couples, and anyone who prefers a fully personalised experience.
Is lunch included in the Chianti wine tour?
Yes. A full traditional Tuscan lunch is included, served at one of the organic wineries we visit, with Chianti Classico wine pairing. The lunch is prepared using local, seasonal ingredients.
What wines will I taste?
Each visit is unique. You will taste Chianti Classico DOCG wines at 2 organic and/or biodynamic estates. The wineries will explain their production methods directly, and you will often meet the producers in person. You can expect to taste around 10 wines across both estates. Chianti Classico DOCG is always included; other labels depend on the winery and the season. Two extra virgin olive oil tastings are also included at the estates.
How long is the Chianti Classico wine tour from Florence?
The tour lasts 6 hours, including pick-up and drop-off in Florence. The day starts in the morning with a scenic drive into the Chianti Classico countryside, and includes visits to 2 organic wineries and a Tuscan lunch at one of them.
Where in Chianti does the tour go?
The tour takes place in the Chianti Classico DOCG, the historic wine zone between Florence and Siena, approximately 40 km south of Florence and 40 km north of Siena. Key towns in the area include Greve in Chianti, Panzano in Chianti, Radda in Chianti and Gaiole in Chianti. We visit organic and biodynamic estates, many of them family-run boutique wineries.
Do you pick up from Florence hotels?
It depends on the option you choose. For private tours, yes: we pick you up directly from your Florence hotel or B&B. For the semi-private tour, the meeting point is in front of Caffè Lietta, Piazza della Libertà 50129, Florence. We also offer private tour departures from Siena: a supplement of approximately €150 applies to cover the additional transfer distance.
Can children join the tour?
For the semi-private tour: no. The minimum age is 18 and children are not permitted. For private tours: yes, children are welcome. The tour is exclusively for your group and can be adapted to your family's needs. Please mention this when booking so we can organise accordingly.
How far in advance should I book?
We recommend booking at least 2 weeks in advance, especially April through October. The organic wineries we visit are small, family-run producers who welcome guests by appointment only, so earlier booking ensures access to the best estates. Last-minute requests are welcome subject to availability.
Who leads the Chianti Classico wine tour?
An expert guide leads the day, in English or Italian. Out of the Box Florence was founded by Stefano Mazzantini, a FISAR-certified sommelier and licensed hiking and cycling guide with 20 years of experience in Tuscany. Thanks to our team of certified sommeliers, we have close relationships with the boutique producers we visit.
Do you take commissions from the wineries?
No. We never accept commissions or payments from wineries, and we never stop at wine shops. You will never visit wine merchants or large-scale producers: we take you to passionate winemakers whose vineyards we know personally.
Can I add a third winery?
Yes, on private tours. A 3rd winery visit can be added for private groups, and the day is fully customisable to your preferences. The semi-private tour visits 2 wineries.
What vehicle will we travel in?
You travel in our own luxurious, air-conditioned minivan with leather seats. Transportation from and to Florence is included in the price.
Is the tour wheelchair accessible?
No. The Chianti Classico wine tour is not wheelchair accessible.