Florence to Chianti & Siena: Wine Tasting & Medieval Towns

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Free cancellationTravelers' pick

1/24

Duration9h

GroupUp to 14

LanguagesEN

Mobile ticketAccepted

Tuscan hills, medieval streets, and a farmhouse lunch that changes how you taste wine

You get picked up in Florence, driven through the Chianti hills to a family farm for a wine-paired lunch, then have free time in the medieval villages of San Gimignano and Siena before returning to the city. Transport, the farm experience, and lunch are all included; groups stay under 15 people, and the minivans let you skip the parking lots and walk straight into the old towns.

Step-by-step itinerary

Tuscan countryside tour and sightseeing

Pick up in central Florence
Drive through Tuscan hills
Stop for panoramic Florence photos
Explore San Gimignano streets freely
Tour family farm vineyards and winery
Enjoy lunch with Chianti wine
Visit medieval town of Siena
See Palio horse race square
Optional visit to Siena Cathedral
Return to Florence by coach

The Experience

You start in the city and end in vineyards—that's the rhythm of this day. Your driver picks you up in central Florence in an air-conditioned minivan, and within an hour you're climbing into the Tuscan hills, past the panoramic viewpoint where Florence shrinks behind you. The contrast hits fast: stone towers rising from nowhere, cypress trees marking the ridgelines, and then San Gimignano appears, a UNESCO village so perfectly preserved it barely feels real. You get free time to walk the narrow streets on your own, no guide narrating—just you, the medieval architecture, and the kind of quiet that makes you understand why people move to Tuscany.

Then comes the farm. Your tour leader takes you behind the scenes at a family-run Chianti vineyard—through the cellars, past the vines, and into a room where lunch is waiting. It's not a restaurant; it's a table with local, seasonal ingredients paired with wines they've selected to match each course. You taste how the wine changes with the food, which is the whole point of wine tasting that actually sticks with you. The meal is included, and so is the wine—no separate bill, no upselling. If you have dietary restrictions, you need to contact them after booking, but they'll work with you (though they note vegans and those with celiac disease are difficult to accommodate here).

Siena comes next, and it's the kind of medieval town that survived World War II almost untouched. You have free time to wander—the Palazzo Pubblico overlooks the Piazza del Campo, where the Palio horse race happens twice a year, and the Siena Cathedral sits nearby if you want to go inside (tickets aren't included, but your tour leader can help you buy them; it's closed Sundays and certain holy days). The streets are steep and narrow, and you're walking at a moderate pace, so this isn't a tour for anyone with mobility challenges or wheelchairs. After you've had your fill, the minivan brings you back to Florence as the light changes over the hills.

Groups stay small—capped at 14 people—which means the minivans can slip into the city centers instead of parking outside and walking in. If your group is larger than eight, your guide splits time between vehicles, but that's the trade for avoiding the parking lot shuffle. The whole day is handled: pickup, transport, the farm visit, lunch, wine, and the drive back. You just show up and move through Tuscany.

What’s included

Your day includes hotel pickup and drop-off in central Florence, professional English-speaking tour leader, designated driver, air-conditioned minivan transport through Tuscany, a stop at the Piazzale Michelangelo panoramic viewpoint, free time to explore San Gimignano and Siena on your own, a behind-the-scenes tour of a Chianti family vineyard and wine cellars, and a gourmet lunch with seasonal local ingredients paired with selected Chianti wines at the farm. The Siena Cathedral exterior is visible during your free time, though interior entry is not included and tickets must be purchased separately.

Good to know

Easy physical levelInfant seats availablePublic transport nearby

Operated by Walks - Italy & Spain

Is this one for you?Right for travelers based in Florence who want a full Tuscan day without arranging transport, vineyard access, or lunch logistics themselves. Plan for moderate walking through medieval towns with steep streets—that's what gives you the authentic village experience instead of a bus-window view.