Florence to Chianti: Small-Group Tuscany Wine & Oil Tour

Summary

Chianti hills, boutique wineries and olive oil tastings with local stories

You’ll sip Chianti wines straight from local cellars, taste fresh-pressed olive oil at a historic mill, share stories with winemakers, and enjoy a three-course Tuscan meal overlooking the vineyards. With pickup from Florence and a friendly local guide leading the way, you’ll feel like part of the countryside — not just passing through.

What’s the experience like?

We’d barely stepped out of the minivan when the first thing I noticed was the smell — kind of earthy, a little sweet, like sun-warmed vines and crushed leaves. Our guide, Paolo, waved us over to meet Signora Lucia at her family’s winery just outside Florence. She handed me a glass before I could even get my bearings. “Try this,” she said in Italian, grinning. I probably looked nervous swirling it (I’m not exactly a sommelier), but she just nodded approvingly. There was something about the way she talked about her olive trees — like they were old friends. I tried to say “grazie” properly; Paolo laughed and corrected me gently.

The drive through Chianti Classico felt almost unreal — castles peeking out between rows of vines, stone farmhouses half-hidden by olive groves. At one point we stopped for photos and I swear you could hear nothing but cicadas and someone’s laughter drifting from a vineyard below. The second winery had these cool underground cellars that smelled faintly of musty barrels and peppery wine. Our group was small enough that it never felt rushed; we asked too many questions about Supertuscans and nobody minded. Lunch was at this boutique estate — pasta with wild boar ragù (I still think about that sauce), crusty bread soaked in their own olive oil, and more wine than seemed strictly necessary for midday.

I wandered off for a minute after lunch while everyone else shopped for bottles. The village of Greve in Chianti isn’t big but there’s something quietly lively about it — old men arguing over cards under faded umbrellas, shop windows full of cheese wheels bigger than my head. The sunlight made everything look softer somehow. Heading back to Florence later, Paolo pointed out the Castello di Vicchiomaggio on the hilltop and told us a story about its ghost (he swears it’s true). I don’t know if it was the wine or just the day itself, but leaving felt oddly bittersweet.

Step-by-step itinerary

Day 1 — Tuscany wine tour and lunch

• Travel from Florence to Chianti region
• Visit first winery cellar and wine tasting
• Visit second winery cellar, tasting, and shop
• Explore Via Chiantigiana and castles
• Enjoy typical Tuscan lunch

Top questions

How long is the Tuscany wine & oil tour from Florence?

The tour is a full-day trip departing from Florence and includes visits to three wineries plus lunch.

Is transportation included in this Chianti wine tour?

Yes, round-trip transportation from Florence is provided by comfortable Mercedes minibus.

Do you visit actual working wineries on this tour?

Yes, you visit three award-winning wineries in the Chianti Classico region with guided cellar tours.

Is lunch included during the day trip to Chianti?

A three-course typical Tuscan meal with wine tasting is included at a boutique estate.

Can children join this Tuscany wine tour?

The tour is suitable for all fitness levels but alcohol is only served to guests 18 or older.

Are olive oil tastings part of this experience?

Yes, you’ll visit an olive oil mill for guided tasting at a historic property.

How many people are in each group?

The standard group size varies; upgrade options allow semi-private groups with max 8 guests.

Is free time available in any villages?

You have free time to explore Greve in Chianti village during the tour.

What’s included

Your day includes pickup and return transport from Florence by Mercedes minibus, guided visits at three wineries in Chianti Classico with cellar tours and tastings, an olive oil mill visit with tasting session, plus a three-course Tuscan lunch paired with local wines — all led by an English-speaking driver or certified wine expert if you choose the semi-private option.