Siena, San Gimignano & Chianti Wine Tour from Florence

Options for this experience

4 options

Guide in French or Italian08:45

Guide in English, Spanish or Portuguese08:45

Guide in English or Spanish08:45

Guide in French, Italian or Portuguese08:45

You pick the guide language when booking.

You see the exact price of each option when you check availability.See dates & prices

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.

Step-by-step itinerary

Stops and time at each

1. Pubblico Palace30m
2. Siena Cathedral30m

Explore Tuscany: Monteriggioni, Siena, San Gimignano

• 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.

Days and timesDaily · 08:45

AgesAges 13+ · 4 to 12 years · Under 4 — Free

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff weari…”

Cancellation and refundsFree cancellation up to 24h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated today

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.

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Top questions

What languages is the guide in?

Live guide in English, Spanish, French, Italian and Portuguese.

Can children come?

4 to 12 years; under 4, free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24h before the start.

How long is the full day tour?

The tour runs from early morning until evening, approximately eight hours total including travel time and all stops.

What's included in the tour price?

Coach transport with WiFi, a multilingual tour leader, free time in Monteriggioni and San Gimignano, a guided or semi-independent Siena visit depending on your option, and Chianti wine tasting with regional snacks at a winery.

Do I have to take the guided tour in Siena or can I explore on my own?

You can choose: the Classic option includes a one-hour guided walking tour with a professional guide, or the Semi-Independent option gives you 2.5 hours of free time to explore Siena at your own pace.

Where do I meet the tour?

Meet your guide at Piazzale Montelungo Bus Terminal, a 5–10 minute walk from Santa Maria Novella train station in Florence.

Is lunch included?

Lunch is not included in the tour price, but you have free time in Siena and San Gimignano to eat at restaurants or cafés of your choice.

Can I visit the inside of the Siena Cathedral or other churches?

The guided tour in Siena shows the Cathedral from the outside. If you choose the Semi-Independent option, you can enter on your own during your free time (entry fees not included).

Is the Chianti wine tasting included?

Yes, the tour includes tastings of 2–3 Chianti wines and regional snacks at a local wine estate in the evening.

Can I walk the fortress walls in Monteriggioni?

Yes, but it costs extra and is optional. You have 45 minutes of free time in the village to decide.