Siena to Florence tour: San Gimignano, Chianti, Monteriggioni

Four medieval and wine-country stops between Siena and Florence in one morning and afternoon.

A private transfer tour from Siena to Florence that stops at four Tuscan landmarks: the 13th-century fortress of Monteriggioni, the UNESCO-protected hill-town of San Gimignano with its surviving towers, the Chianti wine town of Greve in Chianti, and the hamlet of Montefioralle. Your driver-guide provides live commentary in English, Spanish, Italian or French, and hotel pickup and drop-off are included. The full route takes about seven hours.

Step-by-step itinerary

Siena to Florence via Chianti and San Gimignano

• Pick up from accommodation at 9:30am
• Visit medieval fortress of Monteriggioni
• Explore San Gimignano hill-town
• Lunch in San Gimignano (not included)
• Drive through Chianti Classico region
• Visit Greve in Chianti town
• Free time to sample wines and shop
• Walk in picturesque hamlet Montefioralle
• Continue to Florence destination

The experience

You're arriving in Siena or leaving from there toward Florence, and you want to see the countryside and medieval towns in between without renting a car or joining a group. Your driver picks you up from your Siena hotel at 9:30am and heads first to Monteriggioni, a walled fortress the Sienese built in the 13th century as a stronghold against Florence. The complete ring of walls still stands. The town held out against Florentine and Bishop of Volterra forces until the Medicean era, when its captain handed over the keys. You walk the cobbled streets and take in the layout before continuing on.

San Gimignano comes next, the UNESCO-protected hill-town famous for the austere towers that have survived centuries intact. The town sits among vine-covered hills and fills with artisanal shops selling local crafts and saffron, the region's "red gold", alongside restaurants where you can eat on your own. You have leisure time here to browse, eat lunch (your choice of restaurant), and soak in the medieval architecture. After lunch, your driver takes you into the Chianti Classico region on panoramic roads to Greve in Chianti, known for its oval plaza lined with artisan shops and wine stores and as the birthplace of the explorer Verrazzano. You have free time to sample wines and browse. Before reaching Florence, you make one final stop in Montefioralle, a small picturesque hamlet where you walk the cobbled streets and take in the landscape. The full journey ends at your Florence hotel after roughly seven hours.

Your driver provides live commentary throughout the route in your choice of English, Spanish, Italian or French. The minivan is air-conditioned, and hotel pickup in Siena and drop-off in Florence are both included. Specialized infant seats are available if you're traveling with small children.

What’s included

• Hotel pickup in Siena at 9:30am and hotel drop-off in Florence.
• private air-conditioned minivan transportation.
• driver-guide with live commentary.
• stops at Monteriggioni, San Gimignano, Greve in Chianti, and Montefioralle.

Before you book

Days and timesEvery dayDeparts at 09:30

Book up to12h before

GroupPrivate

Live guideEnglish, Spanish, French, German and Italian

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends at a different place from where it starts.You can choose from 7 pickup points.

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

ConfirmationConfirmation within 48 h

Prices and times updated 13 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availableNot recommended with heart problems

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?The seven-hour route means a full morning and afternoon of travel and stops, so book this if you're moving between Siena and Florence anyway and want to see the countryside and medieval towns without driving yourself or joining a larger group.

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Top questions

What languages is the tour guided in?

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

What is Monteriggioni and why does it matter?

Monteriggioni is a 13th-century fortress built by Siena as a defensive stronghold against Florence. Its complete ring of walls survives intact, and you walk through the medieval village to see how it was constructed and laid out as a military bastion.

Can I eat in San Gimignano, and is it included?

Yes, San Gimignano has many restaurants where you can eat lunch on your own. Meals are not included in the tour price, so you choose where and what to eat during your leisure time there.

How much free time do I have in each town?

San Gimignano gives you leisure time in the morning and early afternoon to browse shops and eat lunch. Greve in Chianti offers free time to sample wines and visit artisan shops. Montefioralle is a brief stop for a walk through the hamlet before you continue to Florence.

Does the tour include wine tastings in Chianti?

The tour stops in Greve in Chianti, where you have free time to visit wine stores and sample wines at your own expense. Wine tastings are not arranged or included as part of the tour.