Italy · City Tours

9-Hour Siena San Gimignano and Chianti Tour from Florence

9 Hours Round trip from Piazza del Campo Easy pace

The journey

Trip highlights

01 Explore Siena's famous Piazza del Campo and outstanding Cathedral
02 Travel the scenic Chiantigiana road through castles, vineyards, and hill towns
03 Discover San Gimignano's medieval towers, the "Manhattan of the Middle Ages"
04 Optional lunch at a farm or winery with traditional Tuscan wines and specialties

Discover a unique part of Tuscany on a private day trip from Florence, exploring Siena, San Gimignano, and the renowned Chianti wine region. Visit historic landmarks such as Siena's famous Piazza del Campo and the outstanding Siena Cathedral, then continue through Chianti's scenic roads, castles, vineyards, and hill towns. In San Gimignano, admire its medieval towers and remarkably preserved historic center. You can also add an optional lunch at an organic farm or winery to savor traditional Tuscan wines and specialties.

Admire its Italian Gothic architecture in one of the most significant and spectacular churches built in Italy.

From the itinerary

At a glance

What this trip includes

Duration 9 Hours

Tour type Private

Activity level Easy

Accommodation Not included

Transport Included

Wheelchair access Not applicable

Cities Florence, Siena, Chianti, San Gimignano

Languages English

Day by day

The itinerary

Day 01

Siena's Historic Center and Cathedral

Meet your local tour guide and begin in Siena, one of the most popular and visited places in Tuscany.
Upon arrival, explore its rich history and art through notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral.
See the many local shops that fill Siena's historic streets, offering an excellent opportunity to taste local food or buy souvenirs.
Visit the Cathedral of Santa Maria Assunta, the main location of Catholic worship in Tuscany and the diocese of Siena. The building stands in a square of the same name in the center of the city.
Admire its Italian Gothic architecture in one of the most significant and spectacular churches built in Italy.

Duration: 3 hours

Day 02

Monteriggioni and the Chianti Countryside

Make a lovely stop in the small fortified village of Castello di Monteriggioni, still surrounded by its original medieval walls.
Pass along the SS222 road, better known as the Chiantigiana, one of the most beautiful roads in Italy, stretching through the entire Chianti region from Florence to Siena.
Take this scenic route north from Siena to Castellina in Chianti, through an area rich with castles and villages.
Stop at the Castle of Fonterutoli to admire the small medieval village surrounded by endless vineyards, centuries-old woods, and green hills.
Proceed to Castellina in Chianti for an optional lunch at a farm or winery. This optional activity may take around 2 hours.

Duration: 1 hour 30 minutes

Day 03

San Gimignano's Medieval Towers

See the beautiful stronghold of San Gimignano, one of the most popular tourist attractions in Tuscany.
Explore this treasure of medieval architecture, seemingly frozen in time since 1300 AD.
Visit the ancient towers that still define its skyline, earning the town the nickname "Manhattan of the Middle Ages."
Stop by the famous Dondoli ice cream shop, winner of many awards for the best ice cream in the world.
At the end of the tour, you will be dropped off back at your accommodation in Florence.

Duration: 1 hour

The route

Where you'll travel

Tour route map — Round trip from Piazza del Campo 4 cities · 9 Hours

The fine print

Trip details

What's Included

Pick-up and drop-off at your selected hotel/location in downtown Florence
Private transportation by Mercedes minivan
English-speaking licensed driver
Unlimited packaged drinking water
On-board WiFi

What's Not Included

Lunch on a farm or at a winery, available at an extra cost
Private local tour guide
Tips and gratuities
Any personal expenses

Know before you go

Departure is at 9:30 am.
Pick-up time can be changed upon request.
A confirmation is appreciated the day before the appointment.
Not wheelchair accessible.
Not suitable for pets.
Infants must not sit on laps.
In case of rain, umbrellas are provided by your driver.
This tour/experience is for a maximum of 8 travelers (your private party). Should your group exceed this size, you can make two reservations.
You will be picked up directly at your hotel or address provided at the time of booking at the exact start time of the tour.
Upon request during reservation, lunch in wine cellars or on farms can be organized. This is a highly recommended experience, especially for wine lovers. Vegetarian and gluten-free lunches are also available and can accommodate allergies if requested 24 hours before the tour.
Our drivers are extremely familiar with Tuscany and its main destinations. They will gladly share information, curiosities, and traditions about the area being toured and more, and they are open to any questions and requests.