Florence: Tuscany Wine Tour Siena & San Gimignano Lunch

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Guide in English09:30 and 14:45

Guide in English08:45

Guide in English08:00, 09:00, 13:15 and 14:15

Guide in EnglishFrom 30 Oct · 08:45 and 09:45

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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

Tuscany day trip from Florence

• 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.

Days and timesDaily · 8 departure times, from 08:00 to 14:45

AgesAges 18+ · 7 to 17 years · Under 7

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “Please arrive 15 minutes early to check in for your tour. From Santa Maria Novella Train Station, follow the signs toward Piazzale Montelungo (bus terminal area…”

Cancellation and refundsFree cancellation up to 24h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

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.

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Top questions

Can children come?

7 to 17 years; under 7.

How long is the full-day Tuscany wine tour from Florence?

The full day is 10+ hours, including round-trip coach time and stops in Siena, Chianti, and San Gimignano.

What's included in the winery lunch?

A three-course traditional Tuscan meal with cured meats, cheeses, Lasagne al Tartufo, and ribollita, plus a tasting of six wines paired with artisanal olive oil.

Is there a half-day option?

Yes. The half-day tour focuses on Chianti wineries and lunch only, without Siena or San Gimignano.

Do I need to arrange my own transport from Florence?

No. Round-trip coach transport from central Florence is included. You meet at the point listed on your booking voucher.

Is the guide English-speaking?

Yes, the guide is an expert English speaker.

What's the walking like in Siena and San Gimignano?

Both towns have cobblestone streets, some hills, and uneven terrain. Sustained walking is required, so moderate fitness and broken-in shoes are recommended.

Do I need to be a certain age for the wine tasting?

Yes, participants consuming alcohol must be 18 or older, the legal drinking age in Italy.

Can dietary needs be accommodated?

Contact the operator in advance with any allergies or dietary restrictions, and they will do their best to accommodate.

Is this tour recommended for pregnant travelers?

No, it is not recommended for pregnant travelers due to the sustained walking and uneven terrain.