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Florence: Siena & San Gimignano Day Trip with Winery Lunch

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Free cancellationTravelers' pick

1/20

Duration10h

GroupUp to 25

LanguagesEN

Mobile ticketAccepted

Siena's Cathedral and a Tuscan Lunch That Stays With You

You depart Florence in a small group of no more than a dozen people, guided through Siena's cathedral and main piazza, pause at the fortified village of Monteriggioni, then sit down to a seasonal Tuscan lunch with wine pairing at a working estate. The afternoon is yours to explore San Gimignano's medieval towers and streets before returning to Florence around 6pm. Transport, guide, and lunch are included; the Siena Cathedral entrance (€15) is optional and paid on the day.

10h

Step-by-step itinerary

Depart from Florence
Visit Piazza del Campo in Siena
Tour Siena Cathedral
Pass by Monteriggioni
Visit winery estate and old cellars
Enjoy light Tuscan lunch with wine
Explore San Gimignano medieval town
Free time for shops, church, or gelato

The Experience

So you're standing in Piazza del Campo, and your guide is pointing out the Palazzo Pubblico, and suddenly the whole medieval thing clicks—the way the piazza slopes, the brick, the light hitting it at a certain angle. That's the Siena part of the day, and it happens early, before the crowds thicken. You get a guided walk through the highlights, then free time to wander into the Siena Cathedral if you want (the entrance fee is €15, paid to the guide on the day—it's optional, and honestly, the interior mosaics are worth it). The group stays small, which means you're not herding through with forty other people, and the pace is real: you move, you stop, you breathe.

Then comes the drive through the Tuscan landscape—actual rolling hills, cypress trees, the whole thing—and you stop at Monteriggioni, this fortified village that looks like it fell out of a medieval painting. It's a quick pause, but it's the kind of moment that makes you understand why people come to Tuscany in the first place. After that, you head to a working winery estate where lunch happens. Seasonal Tuscan food—fresh, not fancy—paired with their red wines. You sit down, you eat, you drink something good, and the whole afternoon slows down. No rushing. The minibus has air conditioning and Wi-Fi if you need it, but mostly you just sit there.

San Gimignano is the last stop, and it's the one everyone photographs. The medieval towers are real—fourteen of them still standing—and the town is small enough that you can actually get lost in it without stress. Free time means you choose: walk the main street, look at the Collegiata church, grab a gelato, sit on a stone wall and watch the light change. The driver picks you up around 6pm and you're back in Florence by early evening. It's one day, but it covers four different places, and you're not the one navigating or worrying about parking.

What’s included

Roundtrip transport by air-conditioned minibus (Mercedes or similar) with free Wi-Fi, professional English-speaking guide and driver, guided walking tour of Siena's highlights including Piazza del Campo and the cathedral area, lunch at a Tuscan winery with seasonal local dishes paired with the estate's red wines, free time to explore San Gimignano's medieval town, and luggage storage on the bus. The Siena Cathedral entrance fee (€15 per person) is optional and paid to the guide on the day.

Good to know

Easy physical levelStroller friendlyPublic transport nearby

Operated by Prestige Rent

Is this one for you?Book this if you want to see Siena, San Gimignano, and a working winery in one day without arranging your own transport or timing—the small-group format and fixed schedule handle the logistics, leaving you to focus on the places themselves.