Florence: Siena & San Gimignano Private Tour with Chianti

Medieval Towers & Wine: A Private Tuscany Loop from Florence

You're picked up at your hotel and driven through Chianti vineyards to three medieval towns: Siena (with its famous shell-shaped square and cathedral), the fortified village of Monteriggioni, and San Gimignano (known for its towers). You get free time in each place to explore, eat, and shop. Optional winery lunch with wine pairings is available for an extra fee. Hotel drop-off happens in the evening after 8–9 hours.

Step-by-step itinerary

Explore Siena, Monteriggioni, and San Gimignano

• Travel from Florence to Siena
• Explore Piazza del Campo
• Visit Siena Cathedral
• Walk historic streets and shop
• Stop at Monteriggioni village
• Optional lunch at organic winery
• Visit medieval towers of San Gimignano
• Try award-winning Dondoli ice cream
• Return to Florence

The Experience

Your driver picks you up at your Florence hotel around 9am and heads south into the Chianti region. The landscape shifts almost immediately: vineyards and cypress trees replace the city, and you're moving through the kind of Tuscan countryside that looks the same in every photograph, except you're actually in it. The van fits up to six people, so it's intimate without feeling cramped, and your English-speaking driver knows the roads and the stops well enough that the day doesn't feel rushed.

Siena comes first, and you'll spend a couple of hours there. Piazza del Campo is the obvious draw (that seashell-shaped square where the Palio horse race happens twice a year), but the real pull is just walking the medieval streets, ducking into the Siena Cathedral (built in Italian Gothic style, striped marble and all), and finding a café where you can sit and actually absorb it instead of moving through it. Local shops line the streets, so if you want to grab something to eat or pick up a gift, there's time for that. Your driver doesn't rush you. The schedule is flexible enough that you're not watching the clock.

After Siena, you stop briefly in Monteriggioni, a small fortified village still wrapped in its original medieval walls. It's a short walk and a good place to stretch. Then comes San Gimignano, the one everyone photographs. It's famous for its towers (the nickname is "Manhattan of the Middle Ages," which is a bit much, but the towers are genuinely there and genuinely medieval), and there's a celebrated ice cream shop called Dondoli if you want to try it. You've got free time to wander, and the UNESCO designation means the whole place is preserved in a way that feels less like a museum and more like a town that just happens to be very, very old.

The optional lunch at a local organic winery is worth considering if you're into wine and food. It's an extra €55–65 per person, and it includes several courses paired with Chianti, Super Tuscan, and Vernaccia wines: fresh pasta, cured meats, seasonal vegetables, cheeses, a dessert. If you book the lunch, you'll skip Monteriggioni and have less time in the cities, so it's a trade-off, but it's a good one if that's what you came for. If you skip it, you're back in Florence by evening. The whole thing is private to your group, so the pace and stops are yours to shape.

What’s included

• Your day includes hotel or private address pickup and drop-off in downtown Florence, private air-conditioned minivan transportation, English-speaking driver, on-board WiFi, and unlimited cold mineral water. You get free time to explore Siena (including Piazza del Campo and Siena Cathedral), Monteriggioni, and San Gimignano. Optional traditional lunch at an organic winery with wine pairings is available for €55–65 per person if booked in advance.
• the winery can accommodate allergies and special diets upon request.

Days and timesMon–Fri · 09:00, 09:30 and 10:00

AgesAges 14+ · 7 to 13 years — Free · 2 to 6 years — Free · Under 2 — Free

Meeting point and pickupHotel pickup

Cancellation and refundsFree cancellation up to 24h before the start. After that, no refund.

Prices and times updated today

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by UNIQUETUSCANY private tours

Is this one for you?Best for small groups and families who want to see three medieval Tuscan towns in one day without arranging their own transport or timing: the private van and fixed itinerary mean you're not coordinating logistics, just showing up at your hotel at 9am.

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Top questions

What languages is the guide in?

Live guide in English and Italian.

Can children come?

7 to 13 years, free; 2 to 6 years, free; under 2, free.

What time does the tour start?

Pickup is suggested at 9am, but you can choose a different time during booking.

Is lunch included?

No, lunch is optional. A traditional meal at an organic winery costs €55–65 per person and includes wine pairings. If you skip it, you have free time to eat in the towns instead.

How many people can go?

The tour is private to your group, with a maximum of 6 travelers.

What's included in the price?

Hotel pickup and drop-off in Florence, private air-conditioned minivan, English-speaking driver, on-board WiFi, and unlimited cold water. Entry fees to attractions are not included.

What if it rains?

Your driver provides umbrellas.

Do I need to book the winery lunch in advance?

Yes, you arrange it during reservation. It's not available on the day itself.

Is a professional tour guide included?

No. Your driver is English-speaking and knowledgeable, but an authorized guide is not included.