Pisa, San Gimignano, Siena & Chianti: Tuscany day trip

Four Tuscan towns, one day: from marble towers to wine country to UNESCO medieval squares.

A full-day minivan tour from Florence through Tuscany's most famous towns (Pisa, San Gimignano, Siena and the Chianti region) with stops at the Leaning Tower, a working wine estate for lunch and tasting, and the medieval heart of Siena. Groups stay under eight, and an English-speaking driver provides introductory information at each stop while you navigate the towns on your own pace.

Step-by-step itinerary

Explore Pisa, Chianti, San Gimignano, Siena

• Visit Piazza dei Miracoli in Pisa
• See Leaning Tower and Baptistery
• Drive to country estate for lunch
• Enjoy guided Chianti and Vernaccia tasting
• Explore San Gimignano town center
• Drive past Monteriggioni fortified hamlet
• Visit Siena's Piazza del Campo and landmarks
• Free time to explore Siena Cathedral and streets

The experience

The day starts in Pisa at Piazza dei Miracoli, where the Leaning Tower rises alongside the Baptistery, Cathedral and Monumental Graveyard: all twelfth and thirteenth-century marble structures that UNESCO protects as a single site. You have time to walk the square, photograph the tower and step inside the buildings at your own pace. The driver offers context but does not lead a formal tour. From there, a panoramic drive through Chianti vineyards and olive groves takes you to a country estate where lunch arrives with a guided tasting of Chianti and Vernaccia wines, managed by the farm owner. This is the meal and the wine education built into the day, not an add-on.

After lunch, San Gimignano sits a short distance away: a medieval town still ringed by its original walls and famous for the towers that earned it the nickname "Manhattan of the Middle Ages." Vernaccia wine is produced here, and the town centre holds Piazza della Cisterna, the Cathedral, Palazzo del Podestà and the Church of Sant'Agostino. You explore on foot with free time to wander. The route then crosses back through Chianti to Monteriggioni, a fortified hamlet from the thirteenth century perched on a hilltop, before the final stop in Siena: a UNESCO World Heritage city where Piazza del Campo's shell-shaped plaza holds the Palazzo Comunale and the Torre del Mangia. The Cathedral sits nearby, and narrow streets branch off in all directions. Again, the time is yours to spend.

The minivan is air-conditioned with wi-fi on board, and the driver speaks English. Groups max out at eight people, which keeps the vehicle intimate and the stops unhurried. Hotel pickup from central Florence is included depending on which option you book. The alternative is to meet the group at a central location. The full day runs ten hours from start to return.

What’s included

• Hotel pickup and drop-off from centrally located Florence hotels (depending on the option you select).
• transport by air-conditioned minivan with wi-fi.
• lunch with Tuscan wines including Chianti and Vernaccia.
• guided wine tasting at a country estate.
• English-speaking driver throughout the day.

Options for this experience

2 options

Tuscany Day TripGuide in English · 08:30Small-group Tuscany day trip covering Pisa, Siena, San Gimignano, Chianti and Monteriggioni, departing from Republic Square

Day trip with pick-up from your hotelGuide in English · 08:30Pick-up from hotels in the city center

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

Information

Lasts 10h, runs Monday, Wednesday, Friday and Saturday at 08:30, from € 270 per person, with a live guide in English, in groups of up to 8 and with free cancellation up to 24 h before.

Days and timesMonday, Wednesday, Friday and SaturdayDeparts at 08:30Another day? ›

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to1d before

AgesAdult (9 and older) · Child (3 to 8 years) · Infant (under 3)

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by CAF Tour and Travel - Gray Line Florence

Is this one for you?Choose this tour if you want to see four major Tuscan towns in a single day without driving yourself: the minivan and fixed itinerary pack Pisa, Chianti, San Gimignano and Siena into ten hours. The small group size (up to eight) and included lunch with wine tasting mean you're not stopping for meals on your own or navigating between towns. The trade-off is that you move at the group's pace rather than lingering as long as you might in one place alone.

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Top questions

Can children come?

Yes. Ticket types: Child (3 to 8 years); Infant (under 3).

What exactly happens at the wine estate? Is it a formal tasting or more casual?

The tasting is guided by the estate owner, who manages it with expertise and passion. You're served lunch of typical Chianti products alongside the wines, so it's structured but not rushed. The owner walks you through the selection of Chianti and Vernaccia.

Do I have to climb the Leaning Tower, or can I just see it from outside?

You decide. The Leaning Tower is part of Piazza dei Miracoli, and you have time to explore the square and enter any of the four monuments (the tower, Baptistery, Cathedral or Monumental Graveyard), or simply photograph them from the lawn. The choice is yours.

Is the driver a guide who explains the history and art inside the towns?

The English-speaking driver provides introductory information at each stop and during the drive, but is not permitted to lead formal guided visits inside city centres or provide historical and artistic commentary inside museums or churches. You navigate the towns independently, and the driver is there for context and logistics.

What if I have dietary requirements for the lunch?

Note any specific dietary needs in the Special Requirements field when you book. The lunch is served at the estate with typical Chianti products, so advance notice helps the farm prepare accordingly.