San Gimignano & Siena Day Trip: Private Driver & Wine Tasting

Medieval towers, vineyard lunch, and two UNESCO towns in one Tuscan morning and afternoon

A private day trip from Florence to the medieval hill towns of San Gimignano and Siena, with a winery lunch and wine tasting in between. Your driver picks you up at your hotel, shares stories about the Tuscan estates along the way, gives you free time to walk each town, and returns you to Florence by evening. You can add a private guide for the full day if you want deeper history at each stop.

Step-by-step itinerary

Tuscany day trip from Florence

• Meet private driver at Florence hotel
• Drive 90 minutes to San Gimignano
• Explore San Gimignano town freely
• Drive to Tuscan winery
• Enjoy wine tasting and light lunch
• Tour the winery
• Drive to Siena
• Explore Siena with driver stories
• Visit Piazza del Campo
• Return to Florence hotel

The experience

The day starts with a 90-minute private drive from your Florence hotel through the Tuscan countryside. Your driver shares stories and anecdotes about the villas and estates you pass, setting the scene before you arrive at San Gimignano. The town sits on the UNESCO world heritage list and is known as the "Town of Towers": a medieval hilltop settlement with a skyline of stone towers that rise above the fortified walls. You get free time to walk the village on your own, exploring the narrow streets and the architecture your driver has already introduced.

After San Gimignano, your driver takes you across the valley to a Tuscan winery built inside a converted ancient convent. Lunch there includes a selection of locally produced wines, non-alcoholic beverages, and traditional food. You then tour the vineyard and winery grounds before heading to Siena, the day's final stop. Siena is also a UNESCO heritage site, and your driver guides you from site to site while sharing the city's history and giving you time to explore on your own. The tour includes a stop at Piazza del Campo, the famous shell-shaped square where the horse race Il Palio takes place twice a year.

The full day runs about eight hours, ending with a return drive to your hotel in Florence. If you want more in-depth knowledge of the towns and their history, you can choose the option with a private guide who stays with you throughout the day instead of just your driver. Either way, the car is private and the route is the same. The difference is whether you get a guide's detailed commentary or your driver's lighter stories and anecdotes.

What’s included

• Round-trip private hotel pickup and all-day private luxury car through the Tuscan hills.
• free time to explore San Gimignano and Siena on your own.
• lunch with locally produced wines and non-alcoholic beverages at a Tuscan winery.
• a personal tour of the winery and vineyard grounds.
• your driver's stories and anecdotes about the estates and history along the way (or a private guide's deeper commentary if you choose that option).

Options for this experience

2 options

Option Without GuideGuide in English · 09:00Private driver only, with no guide: this option includes a private driver but does NOT include a full-day private tour guide. Pickup is included.

Option with a private guideGuide in English or Italian · 09:00Full-day private guide: this option includes a private tour guide on board who stays with you for the whole day. Pickup is included.

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

Information

Lasts 8h, runs every day at 09:00, from € 550 per person, with a live guide in English and Italian, as a private tour and with free cancellation up to 24 h before.

Days and timesEvery dayDeparts at 09:00

GroupPrivate

Live guideEnglish and Italian

Meeting point and pickupHotel pickup included.

Book up to1d before

AgesAdult (18 and older) · Child (3 to 17 years) · Infant (under 3): free

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

Prices and times updated today

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by LivTours

Is this one for you?Book with just the driver if you prefer to set your own pace and hear lighter stories about the landscape and towns as you go. Add the private guide option if you want detailed historical knowledge of San Gimignano and Siena woven through the day.

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Top questions

What languages is the tour guided in?

Live guide in English and Italian.

Can children come?

Yes. Ticket types: Child (3 to 17 years); Infant (under 3): free.

What is Piazza del Campo, and why does the tour stop there?

Piazza del Campo is a world-famous square in Siena shaped like a shell. It is the site of Il Palio, a horse race held twice a year that draws crowds from across the region. The tour stops there so you can see the square itself and imagine the spectacle of the race, even if you are visiting outside race season.

Do I need to book the private guide option, or can I do the tour with just the driver?

You choose at checkout: the tour works with just your private driver, who shares stories and anecdotes about the estates and towns, or you can upgrade to a private guide who stays with you all day for deeper historical knowledge of San Gimignano and Siena. Both options include the same stops and free time to explore.

Does the tour include pickup from my hotel in Florence?

Yes, your private driver picks you up at your hotel in Florence in the morning and returns you there at the end of the day. The round-trip hotel pickup is included in the tour.