Private Tuscany Tour from Florence: Siena, San Gimignano, Chianti

Your own driver, your own pace through three Tuscan towns and vineyard hills

A private guided tour from Florence visiting Siena, San Gimignano and the Chianti wine region with hotel pickup and drop-off in a luxury Mercedes. You spend two hours exploring medieval Siena on your own, an hour wandering San Gimignano's hilltop streets and towers, then drive through Chianti's rolling vineyards with photo stops whenever something catches your eye. Wine tasting at a local estate is optional. The driver stays at your service the whole day, commentary included, and you can customize the itinerary as you go.

Step-by-step itinerary

Stops and time spent at each

1. Pubblico Palace30m
2. Siena Cathedral15m

Explore Siena, San Gimignano and Chianti

• Pickup from Florence accommodation
• Drive to Siena through rolling hills
• Explore Siena independently for two hours
• Visit Piazza del Campo and enjoy cappuccino
• Tour Siena Cathedral and Piccolomini Library
• Drive to San Gimignano and view medieval towers
• Explore San Gimignano for one hour
• Visit Piazza della Cisterna and enjoy gelato or coffee
• Drive through Chianti region with photo stops
• Optional wine tasting at local Chianti estate
• Return to Florence accommodation

The experience

You're picked up from your Florence hotel in a private Mercedes and driven an hour through rolling Tuscan hills to Siena, a UNESCO World Heritage city built on medieval glory. Your driver drops you near the Cathedral and leaves you free to wander for two hours: no group, no set pace, no schedule beyond when the car returns. You'll find Piazza del Campo, the famous oval square where locals rest on the slopes and the annual palio horse race tears through the neighborhoods, and the Cathedral itself, its facade striped in pink, green, white and black marble, its interior floor carved with 56 biblical scenes in marble and its walls hung with Renaissance masterpieces by Donatello, Michelangelo and Pinturicchio.

From Siena, your driver takes you to San Gimignano, a hilltop town still ringed by thirteen medieval towers: sometimes called a medieval Manhattan. You get an hour to explore the characteristic alleyways, find Piazza della Cisterna at the center, grab a gelato, and stand at the panoramic viewpoint looking out over olive groves and vineyards. The driver waits. You move at your own rhythm through both towns.

The drive back to Florence runs through the Chianti wine region, and here the private format changes everything: you can ask the driver to stop whenever the landscape pulls you in. The rolling hills, tiny villages and castles dotting the slopes are yours to photograph without a group moving on. If you've chosen the wine tasting option, the driver takes you to a local wine estate in the heart of Chianti, where a producer walks you through the vineyards and you taste Chianti Classico with fresh local products. Without it, you simply drive through, stopping where you like. Either way, your driver brings you back to your Florence hotel at the end of the day.

What’s included

• Hotel pickup and drop-off in Florence.
• private Mercedes with air conditioning and USB chargers.
• expert driver speaking your chosen language (English or Spanish).
• eight hours of independent exploration in Siena, San Gimignano and the Chianti wine region.
• photo stops along the way.
• optional wine tasting at a local Chianti estate with vineyard walk and Chianti Classico tasting (if selected at checkout).
• commentary on board.
• dedicated office support to customize the experience before and after the tour.

Options for this experience

4 options

Private tour conducted in English08:30, 09:00, 09:30 and 10:00Pickup is included

Private tour conducted in Spanish08:30, 09:00, 09:30 and 10:00Pickup is included

Private Spanish tour with wine tasting08:30, 09:00, 09:30 and 10:00Spanish-language tour with wine tasting: enhance your private outing with a wine tasting at a charming winery in Chianti, pickup is included

Private English tour with wine tasting08:30, 09:00, 09:30 and 10:00Enhance your private experience with a wine tasting at a charming winery in Chianti, pickup is included

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

Before you book

Days and timesEvery dayDepartures at 08:30, 09:00, 09:30 and 10:00

Book up to2d before

GroupPrivate

Live guideEnglish and Spanish

Meeting point and pickupHotel pickup included.

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

Prices and times updated 9 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePets welcomePublic transport nearbyNot recommended with heart problemsInfants must sit on laps

Operated by Ciao Florence Tours Srl

Is this one for you?Choose this if you want a private driver for the day so you can stop freely in Chianti or explore Siena and San Gimignano at your own pace, rather than moving with a group on a fixed schedule.

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Top questions

What languages is the tour guided in?

Live guide in English and Spanish.

What's the difference between the tour with and without wine tasting?

The wine tasting option adds a stop at a local Chianti estate where a producer guides you through the vineyards and you taste Chianti Classico with local food. Without it, you drive through the wine region with photo stops but no estate visit. Both options include the same Siena and San Gimignano exploration.

How much time do I actually spend in each town?

You have two hours to explore Siena on your own, an hour in San Gimignano, and the rest of the eight-hour day is spent driving between towns, through Chianti, and at the optional wine tasting if you add it. The driver stays with the car and is ready whenever you return.

What happens if I want to stop somewhere along the way?

One of the perks of a private tour is flexibility: simply ask your driver and they'll pull over whenever you see something worth photographing or exploring. The itinerary can be tailored as you go.

Is lunch included?

Lunch is not included in the tour price. You'll have time to eat at cafes and restaurants in Siena and San Gimignano, and your driver can recommend local spots.

What's the vehicle like?

You travel in a fully-fitted luxury Mercedes with air conditioning, USB chargers on board, and free WiFi. The vehicle is sized for up to eight people per booking.