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A guide to private tours from FlorenceTwo days in the Tuscan hills.

How long each one takes, what is included, and which to pick if you only have one day.

Florence is the reason most people come to Tuscany, but the hill towns and vineyards around it are what they remember. Both of our Florence days head south, into the country between Florence and Siena.

If you want the wine: Chianti. If you want the towns: Siena and San Gimignano, which still comes home through Chianti.

The two, side by side

TripLengthLeavesPrice
Chianti Wine Tour from Florence8h07:00from €610
Siena and San Gimignano Day Trip from Florence10h07:00from €470

Prices are starting prices and depend on the size of your group.

How to choose

You want the wine

The Chianti wine tour. Eight hours on the old road between Florence and Siena: the market town of Greve, two family wineries with different styles, a long lunch in Panzano, and the walled village of Castellina. The villages are worth the day even if you do not drink.

You want the medieval towns

Siena and San Gimignano. Ten hours: the fourteen surviving towers of San Gimignano early in the day, lunch at a winery below the town, the Piazza del Campo and the striped marble cathedral in Siena, and home through Chianti. The walled village of Monteriggioni can be added on the way.

Four things worth knowing before you book

Someone else drives

That is the point of a wine day. Your driver takes the car, and nobody in your group has to stay sober for the road home.

Tastings and lunch are paid on the day

Wine tastings are paid at the estate and depend on the wines you choose. Lunch is not included on either tour, but both days are built around time for it.

Private costs less than you think for a group

A coach seat is cheap for one person and stops being cheap at four. Our prices are by group size, not per seat: up to four of you share one car at one price, and the price only steps up when you need a van. And you are not waiting for forty strangers at every stop.

You can change your mind

Free cancellation up to 24 hours before pick-up, refunded in full. If the date stops working, message us and we will do our best to move you to another day.

Start with one of these

See all our private tours in Italy