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Florence: Tuscany Wine Tour Siena & San Gimignano Lunch

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Free cancellationTravelers' pick

1/24

Duration9h

GroupUp to 40

LanguagesEN

Mobile ticketAccepted

Three Tuscan towns and a winery lunch, all in one coach ride from Florence

You travel by coach from Florence through Siena's medieval center, stop at a family-run Chianti winery for a guided cellar tour and six-wine tasting paired with a three-course Tuscan lunch, then finish in the hilltop town of San Gimignano with free time to explore. Round-trip transport, an English-speaking guide, and all meals are included; the full day runs 10+ hours and involves sustained walking on uneven terrain in two towns.

Step-by-step itinerary

Meet tour leader in central Florence
Board air-conditioned coach to Tuscany
Walking tour of Siena's Piazza del Campo
Free time to explore Siena or cathedral
Visit family-run Chianti vineyard estate
Tour vineyard and wine tasting
Enjoy three-course Tuscan lunch
Travel to San Gimignano hilltop town
Free time to explore San Gimignano
Return coach ride to Florence

The Experience

Your coach is already rolling when you settle in—the driver navigates out of Florence's traffic while your guide runs through the day ahead. By the time you reach Siena, about an hour later, you're ready to walk. The medieval city spreads out around Piazza del Campo, the famous square where the Palio horse race tears through twice a year, and your guide points out the Palazzo Salimbeni, the world's oldest bank still operating from its original building. You get free time to wander the cathedral, grab a coffee, or just sit in the piazza and watch the light change on the brick facades. It's the kind of stop that feels unhurried even though the day is full.

Then you're back on the coach heading into Chianti, where the landscape flattens into vineyards and cypress trees. The family-run winery sits quiet until you arrive—no crowds, just the cellar and the tasting room. A staff member walks you through six wines, each one paired with artisanal olive oil, and then lunch arrives: a three-course spread that includes cured meats, cheeses, Lasagne al Tartufo, and ribollita, the Tuscan bread soup that tastes nothing like what you'd expect. Wine is poured again. The meal takes time, which is the point. You're not rushing through a tourist lunch; you're eating what the region eats.

San Gimignano comes last, and it's the visual payoff—a hilltop town so dense with medieval stone towers it earned the nickname Medieval Manhattan. The UNESCO listing is real, but what matters is the cobbled streets are narrow enough that you can touch both walls, and the light at the top of the town hits the towers in a way that makes you stop walking just to look. You have free time to wander, buy gelato, browse the small shops. The walk is sustained and uneven—cobblestones, some hills—so wear shoes you've already broken in. By the time you're back on the coach for the ride home to Florence, you've moved through three different Tuscany moods in a single day, and the guide has probably already given you the names of three restaurants you should try tomorrow.

What’s included

Your day includes round-trip coach transport from central Florence, an expert English-speaking guide, a walking tour of Siena with free time in the medieval center, a guided cellar tour at a family-run Chianti winery, a curated tasting of six wines paired with artisanal olive oil, a traditional three-course Tuscan lunch with cured meats, cheeses, Lasagne al Tartufo, and ribollita, and free time to explore the UNESCO-listed hilltop town of San Gimignano before returning to your Florence drop-off point in the evening.

Good to know

Moderate physical levelInfant seats availablePublic transport nearbyNot for pregnant travelers

Operated by The Tour Guy

Is this one for you?Book this if you want the main Tuscan highlights—wine, medieval towns, and a proper lunch—without arranging transport, timing stops, or figuring out which winery to visit; the fixed itinerary and English guide handle all three, and the coach means you can relax between towns instead of navigating roads yourself.