Florence to Siena & Chianti: Private Wine Tour with Pickup

Summary

Private day trip from Florence with wine tasting in Chianti

You’ll travel from Florence to Siena and Chianti with a local driver who helps shape your perfect day—village stops, private winery tour with tastings, time for Tuscan food if you want it, then wandering Siena’s famous squares before heading back as the sun dips low over those hills you’ll remember long after the trip.

What’s the experience like?

Hands gripping the edge of my seat, I watched the cypress trees flick past as our driver—Marco, who greeted us like old friends—navigated those winding roads out of Florence. He asked if we’d ever tried real Chianti before, and when I hesitated, he just grinned and said, “You will today.” The air outside smelled faintly of earth and something sweet—maybe wildflowers? Greve in Chianti was our first stop, and honestly, I didn’t expect the square to feel so lived-in. Locals chatting over espresso, a butcher shop window full of things I couldn’t name (Marco insisted we try finocchiona; I still can’t pronounce it right).

The drive through Chianti’s hills was quieter than I thought it’d be. Just us, vineyards rolling out on both sides, sunlight flickering through olive branches. Marco pointed out Panzano’s church tower in the distance—he said it’s halfway between Florence and Siena, which made me laugh because it felt like we were in the middle of nowhere (in a good way). At the winery, the cellars were cool and smelled like old wood and grapes. Our guide there explained how they make Chianti Classico—she even let us taste olive oil straight from the estate. It was peppery and green; totally different from what I buy at home.

If you’re into food (who isn’t?), there’s this family-run spot nearby called La Locanda di Pietracupa. We almost skipped lunch but ended up sharing pasta with wild boar ragù that I’m still thinking about. Siena came after—a quick walk from where Marco dropped us off by the cathedral. The marble stripes on the Duomo looked unreal in the late afternoon light. Piazza del Campo was busier than I expected; kids chasing pigeons, someone strumming a guitar off to one side. We wandered without much of a plan—sometimes that’s better anyway.

The drive back to Florence was quiet again. Maybe it was all that wine or maybe just tired in a good way. There’s something about seeing Tuscany this way—with someone local showing you around—that makes everything feel less like a checklist and more like you’re actually part of it for a day.

Step-by-step itinerary

Day 1 — Siena and Chianti Wine Tour

• Drive to Greve in Chianti and explore village
• Drive through Chianti wine road
• Pass by Panzano in Chianti village
• Visit winery and wine tasting
• Optional lunch at La Locanda di Pietracupa
• Visit Siena Cathedral and Piazza del Campo
• Drive back to Florence

Top questions

How long is the drive from Florence to Greve in Chianti?

About 45 minutes by private vehicle with your driver.

Is pickup included for this private wine tour?

Yes, hotel pickup in Florence is included.

Do we visit more than one winery on this day trip?

The tour includes a guided visit and tasting at one Tuscan winery.

Can we customize our itinerary during the tour?

Yes, your driver discusses options so you can tailor your day.

Is lunch included on this private day trip?

No, lunch is not included but there are recommended local restaurants nearby.

Are infants or small children allowed on this tour?

Yes, infants and small children can join; specialized seats are available.

What villages do we stop at besides Siena?

You’ll stop at Greve in Chianti and pass through Panzano in Chianti en route.

Is an English-speaking guide provided at the winery?

The winery visit includes an English-speaking guide for the tour and tastings.

What’s included

Your day includes private transportation with hotel pickup in Florence, an initial briefing with your English-speaking driver to help shape your itinerary, a guided visit of one Tuscan winery with wine and olive oil tastings, plus time to explore villages like Greve in Chianti and Siena before returning comfortably in the evening.