Florence: Siena & Chianti Wine Tasting Private Day Trip

Rolling vineyards, a winery cellar, and Siena's brick-paved square in one day from Florence

You're picked up at your Florence hotel and driven through Chianti wine country in a private Mercedes with an English-speaking driver who customizes the route to your interests. The day includes a stop in Greve in Chianti, a guided winery tour with wine and olive oil tasting, and a late-afternoon visit to Siena's cathedral and famous Piazza del Campo. You return to Florence in the evening, having seen the landscape and tasted the wine without arranging transport, tickets, or timing yourself.

Step-by-step itinerary

Explore Chianti and Siena highlights

• Meet driver at Florence accommodation
• Drive 45 minutes to Greve in Chianti
• Visit Piazza Matteotti and local shops
• Drive 30 minutes through Chianti wine road
• Admire Panzano in Chianti village
• Tour winery and learn wine making
• Taste Chianti wines and olive oil
• Optional lunch at La Locanda di Pietracupa
• Visit Siena Cathedral and Piazza del Duomo
• Walk to Piazza del Campo and explore
• Drive 1 hour back to Florence accommodation

The experience

The driver arrives at your Florence hotel in the morning, and you settle into a Mercedes for the 45-minute drive south into Chianti Classico. The landscape shifts almost immediately. The city grid gives way to hills, and the hills fill with vineyards that roll toward the horizon in waves. Your driver knows this route and the villages on it, and he'll talk through what you want to see and taste before you arrive anywhere, so the day stays yours to shape. That flexibility is the whole point of a private day trip: no fixed stops, no group pace, no schedule that doesn't fit what you actually want to do.

Greve in Chianti comes first, a village built around a sloping square where locals have shopped for wine and food for centuries. You walk past the Enoteca Le Cantine, one of Tuscany's largest wine shops, and the butcher Falorni, which has been there since 1806. The square itself, Piazza Matteotti, is the kind of place where you can sit for twenty minutes and feel the rhythm of a small town that has no reason to hurry. From here, the drive to the winery takes another 30 minutes through the heart of the Chianti wine road, past Panzano in Chianti, a hilltop village with a castle tower and a church that sits exactly halfway between Florence and Siena. The road itself is the experience: vineyards, olive groves, stone farmhouses, and light that changes every few kilometers.

At the winery (typically Fattoria Montecchio, or another estate in the same area if that one is booked). You get a tour of the cellars and an explanation of how Chianti Classico is made, followed by a tasting of several wines (Chianti Classico, Riserva, Super Tuscan) and local olive oil. It's not a rushed tasting. You sit, you taste, you ask questions. If you want lunch, your driver can take you to La Locanda di Pietracupa, a family-run restaurant five minutes away that serves genuine Tuscan food with local wine pairings, though that's at your own cost and entirely optional. Many people skip the restaurant stop and save their appetite for Siena.

Siena arrives in the late afternoon. Your driver drops you at Piazza del Duomo, in front of the cathedral and its bell tower, then you walk five minutes downhill to Piazza del Campo, the brick-paved square where the Palio horserace happens twice a year and where the Town Hall's Mangia Tower rises above the surrounding palaces. It's one of the most recognizable squares in Italy, and seeing it in person after hours of driving through wine country feels like arriving at the end of a story that makes sense. You have time to walk it, sit in it, photograph it, or just stand there. The drive back to Florence takes about an hour, and by then the day has the weight of something complete.

What’s included

• Your day includes hotel pickup and drop-off in Florence, private transportation in a Mercedes with an English-speaking driver, a briefing with the driver to customize your itinerary, a guided visit to a Tuscan winery with a tour of the cellars and explanation of wine-making, and a tasting of Chianti Classico, Riserva, Super Tuscan wines, and local olive oil. Stops in Greve in Chianti and Siena are included.
• lunch is optional and at your own expense.

Before you book

Days and timesEvery day5 departure times: the first at 08:00, the last at 10:00

Book up toStart time

GroupPrivate

Live guideEnglish

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 3 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by Prestige Rent

Is this one for you?This suits travelers who want to see Chianti and Siena in one day without renting a car or coordinating their own transport and winery bookings. The driver handles the route and timing, which is what makes a full inland day possible from Florence.

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Top questions

How long is the full day trip?

Around 10 hours total, including pickup from your Florence hotel, the drive to Chianti, the winery visit, time in Siena, and the return drive.

Is the itinerary fixed or can I change it?

It's customizable. Your driver discusses options during the drive to Greve and adjusts the day to suit what you want to see and do.

What's included in the winery tasting?

A tour of the wine cellars, explanation of the wine-making process, and a tasting of Chianti Classico, Riserva, Super Tuscan wines, and local olive oil.

Is lunch included?

No. Lunch is optional and at your own expense. Your driver can recommend La Locanda di Pietracupa or other restaurants, or you can eat in Siena instead.

How many people can go on this tour?

It's a private tour for you and your party: no group size limit is specified, but it's designed for small groups traveling together.

What if the winery I want isn't available?

If Fattoria Montecchio is booked, you'll visit another winery in the same Chianti area with the same experience.

Is the vehicle air-conditioned?

Yes, the Mercedes is fully equipped and air-conditioned.

Can I bring a baby or small child?

Yes. Infants can travel in a pram or stroller, and specialized infant seats are available.