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Siena, San Gimignano & Chianti Wine Tour from Florence

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Free cancellationTravelers' pick

1/40

Duration10h 30m

GroupUp to 50

LanguagesEN · PT +3

Mobile ticketAccepted

Three Medieval Towns & a Chianti Winery in One Day from Florence

You travel by luxury coach from Florence to three medieval towns—Monteriggioni, Siena, and San Gimignano—with free time to explore each one. A professional guide leads a one-hour walking tour in Siena (Classic option) or you roam for 2.5 hours on your own (Semi-Independent). The day ends with Chianti wine tasting and regional snacks at a local estate before returning to Florence in the evening.

10h 30m

Step-by-step itinerary

Meet guide at Piazzale Montelungo
Travel to Monteriggioni by coach
Listen to guide's introduction of Monteriggioni
Free time to explore Monteriggioni village
Optional walk on Monteriggioni fortress walls
Travel to Siena
Guided walking tour of Siena highlights
Admire Piazza del Campo exterior
View Palazzo Pubblico and Torre del Mangia
See Siena Cathedral from outside
Travel to San Gimignano after lunch
Free time to explore San Gimignano streets
Optional visit to Collegiata church
Optional gelato at Gelateria Dondoli
Return to Florence by coach

The Experience

What if you could see three of Tuscany's most famous towns without renting a car or figuring out the drive yourself? You meet your guide at Piazzale Montelungo Bus Terminal early in the morning—it's just a 5-10 minute walk from Santa Maria Novella train station—and climb aboard a Gran Turismo luxury coach with WiFi. The drive to Monteriggioni takes about an hour, and your guide fills the time with stories about the hills rolling past the windows, the towns you're heading toward, and how Tuscany actually works. By the time you arrive, you're not just dropped off; you already know what you're looking at.

Monteriggioni comes first—a medieval fortress perched on a hilltop that looks like it was built yesterday and then left alone for 500 years. You get 45 minutes to walk the village squares, climb the fortress walls if you want (that costs extra), and just sit with the view. Then it's on to Siena, and here's where the tour splits: if you book the Classic option, a professional guide walks you through the city for an hour, pointing out Piazza del Campo from the outside—that shell-shaped square where the Palio horse race happens—and the Gothic facade of the Siena Cathedral. If you choose the Semi-Independent option, you get 2.5 hours on your own to go inside the cathedral, eat lunch wherever you want, or just wander. After Siena, San Gimignano is next: the medieval town famous for its towers, cobblestone streets, and the award-winning Gelateria Dondoli in the main square (gelato not included, but worth the detour).

The day ends at a Chianti wine estate in the evening, where you taste 2–3 local wines with regional snacks before the drive back to Florence. The whole thing is about eight hours door-to-door, and you're not managing logistics—the guide handles timing, the coach handles the drive, and you handle deciding whether to walk the fortress walls or sit in a Siena square with a coffee. The bus has WiFi, so you can send photos home while you're still in the hills.

What’s included

Your day includes hotel or train station pickup coordination, Gran Turismo luxury coach transport with WiFi, a multilingual tour leader, 45 minutes in Monteriggioni with optional fortress wall access, either a one-hour guided walking tour of Siena's main sights (Classic option) or 2.5 hours of free time to explore on your own (Semi-Independent option), free time in San Gimignano to browse shops and visit the award-winning gelato shop, and an evening visit to a Chianti wine estate with tastings of 2–3 local wines and regional snacks before returning to Florence.

Good to know

Moderate physical levelStroller friendlyInfant seats availablePublic transport nearbyNot for heart conditionsInfants must sit on laps

Operated by Ciao Florence Tours Srl

Is this one for you?Book this if you want to see three of Tuscany's most famous medieval towns and taste Chianti wine in a single day without driving yourself or piecing together separate tickets and transport—the fixed schedule and included coach handle all the logistics, leaving you free to walk, explore, and eat at your own pace.