Florence: Chianti Wine & Olive Oil Tour with Tuscan Lunch

Three wineries, one unforgettable afternoon in Chianti

You spend the day in a Mercedes minivan with an expert guide, moving between three estates in the Chianti Classico region. You taste olive oil at a historic mill, learn to evaluate wine in a boutique winery's cellars, wander a medieval village, and eat a three-course Tuscan lunch paired with estate wines. Transport from Florence, all tastings, and the meal are included. The semi-private upgrade (max 8 guests) adds deeper cellar access and a focus on Supertuscan wines if you want it.

Step-by-step itinerary

Tuscany wine, oil, and village tour

• Meet guide in Florence
• Drive to Tuscany in Mercedes minivan
• Visit historic olive oil mill
• Olive oil tasting session
• Tour boutique Chianti winery
• Wine tasting and vineyard walk
• Explore medieval Tuscan village
• Enjoy 3-course Tuscan lunch with wine
• Return to Florence and relax

The experience

The Mercedes pulls out of Florence while you're still settling in, and soon the city noise has given way to the sound of gravel under tires and vineyards rolling past both windows. Your guide is already talking you through what's ahead: three estates, two tastings, one lunch, and the kind of afternoon where you stop trying to take photos and just watch the light change on the hills. This is the Chianti Classico region, and it looks exactly like the postcards, except you're driving through it instead of looking at it.

The first stop is an olive oil mill set into a hillside, surrounded by silver-leafed groves and cypress trees that seem planted by someone with a very specific idea of beauty. Inside, the guide walks you through the whole thing: how the olives move from branch to press, what the smell tells you about quality, why the color matters. Then you taste. Real tasting, not just "here's some oil." You learn to notice the peppery finish, the grass notes, how it coats your mouth differently depending on when the olives were picked. It's the kind of detail that sounds small until you taste the difference yourself. After that, you drive deeper into the region to a boutique winery where the cellars are cool and old and the vines outside stretch toward the horizon. The sommelier pours a flight of Chianti and Chianti Classico, and this is where the day shifts. You're not just drinking wine, you're learning to read it. Structure, acidity, tannin weight, how the high acid in these wines is actually what makes them sing with food. You walk through the vineyards while you're still thinking about what you just tasted.

There's a medieval village somewhere in the middle of all this: cobblestone streets, a church, the kind of quiet that makes you realize how loud everywhere else is. You get free time to wander, and your guide shares a few local stories about the region's past before stepping back. Then lunch happens at a second estate, and this is where everything clicks into place. Three courses of actual Tuscan food, not restaurant interpretations, but the kind of thing people eat when they're not trying to impress anyone. Regional dishes built on seasonal, local ingredients, made the way they've been made here for decades. The sommelier sits down with you and talks through how the wine you tasted this morning is supposed to work with what's on your plate. The acidity cuts through the richness. The tannins grip the salt. It's not magic, but it feels like it until someone explains it.

On the drive back to Florence, the light is doing that thing it does in late afternoon. Everything gold and long-shadowed. You're quiet, mostly. Your guide answers questions if you have them, but there's no pressure. You've got the afternoon in your head and the kind of tired that comes from paying attention to things all day. The Mercedes pulls back into Florence, and the city feels different somehow: smaller, or maybe you're just bigger now.

What’s included

Your day includes round-trip transport from Florence in a comfortable Mercedes minivan, guided visits to three award-winning estates (two wineries and one olive oil mill), professional tastings at each estate, a 3-course Tuscan lunch with wine pairings at a boutique estate, free time in a medieval village, an English-speaking guide, and free WiFi on board. If you choose the semi-private upgrade, your group is capped at 8 guests and your guide is a certified wine expert with deeper cellar access and a focus on Supertuscan wines.

Options for this experience

3 options

Wine tour and tasting, half dayGuide in English · 17:00A five-hour half-day trip from Florence to Chianti, including a local food tasting and a wine escape.

Small-group wine and olive oil tourGuide in English · 09:00Minibus or minivan with air conditioning for groups of up to 20 people, with tastings at 3 wineries and 1 olive oil mill, a typical Tuscan lunch, and a visit to a medieval village.

Semi-private Supertuscan WineGuide in English · Available from 26 Mar 2027Upgraded wine experience for groups of up to 8 people, visiting top-quality wineries with your own dedicated wine expert, with a 3-course Tuscan lunch included.

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesEvery dayDepartures at 09:00 and 17:00

Book up toStart time

AgesAdult (13 and older) · Child (4 to 12 years) · Infant (under 4)

GroupUp to 20

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

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

Prices and times updated today

Good to know

Low physical effortInfant seats availablePublic transport nearby

Operated by Towns of Italy

Is this one for you?Right for travelers who want to understand Chianti wine and Tuscan food culture in one day without arranging their own transport or timing: the fixed schedule and expert guide handle both.

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Top questions

Can children come?

Yes. Ticket types: Child (4 to 12 years); Infant (under 4).

What's included in the price?

Mercedes minivan transport from Florence, guided visits to three wineries and an olive oil mill, all tastings, a 3-course Tuscan lunch with wine pairings, and an expert guide.

Can I upgrade to a smaller group?

Yes. The semi-private upgrade limits the group to 8 guests maximum, includes a certified expert sommelier, premium tastings, and a special focus on Supertuscan wines with in-depth cellar visits.

Is lunch included?

Yes. A 3-course gourmet Tuscan meal at a boutique estate, with wine pairings chosen by your sommelier.

Do I need wine experience to join?

No. The guide teaches you how to taste and evaluate wine as you go. You become a sommelier for the day, starting from scratch.

Is there free time in the medieval village?

Yes. You get unscheduled time to explore the cobblestone streets, shops, and views on your own before moving to lunch.

What happens if it rains?

The tour runs rain or shine. You'll still visit the estates and enjoy the tastings and lunch.

Do I need to be fit or able to walk a lot?

The tour is suitable for all fitness levels. There is walking through vineyards and village streets, but nothing strenuous. Your pace is your own.