Chianti’s Best – Private tour

From Siena to San Gimignano, passing through Monteriggioni, and stopping at a winery: a tour designed to let you capture the essence of the Chianti wine region

The Chianti’s Best tour is for those who really want to learn more about Italy’s rich culture, ancient history, customs, and habits. And, of course, want to know more about the famous Tuscan cuisine. Come with us to experience the most authentic Tuscany!

Make a booking


Starting from € 127 / Person
Tour duration

09:00 hours - full day

Private tour - Max 8 people in the VAN
Level: easy

Most travelers can participate
The towers of San Gimignano, second stop of this tour to the best of Chianti

Let us take you to San Gimignano, Monteriggioni, Siena, and a wine estate during this full day Chianti tour.

A landscape showing the Siena skyline in a beautiful Sunny Day. Siena is the second stop of this tour of Chianti for small groups

Leave the crowded streets of Florence behind for a day trip in the Chianti region. The first stop will take us to San Gimignano, known for its fascinating Medieval architecture. Afterwards you will visit Siena, one of Italy’s best preserved Medieval cities, a definite must see when visiting Tuscany. Our third stop will take you to the walled Medieval castle of Monteriggioni – a real hidden gem of Tuscany. We will finish off the day in style by visiting a local winery.

Tour Itinerary



Your tour starts from Florence: we will pick you up at your accommodation if located downtown



Enjoy 60 minutes of free time to visit San Gimignano. Don’t forget to eat some of the best ice-cream Italy has to offer!



90/100 minutes to stroll through the Medieval streets of Siena. Visit a museum, do some shopping or have some food. The choice is yours



30 minutes of time to explore the walled medieval castle of Monteriggioni



Finish off the day in style by visiting a local winery. Learn more about Chianti’s wine history and experience some typical wines of the region



Back to Florence in time for dinner. But before we will have one last stop at Piazzale Michelangelo to enjoy the most celebrated view of Florence


The city center of San Gimignano, first stop of this tour to Siena and San Gimignano


Our first stop will lead us to San Gimignano, famous for its many towers and its astonishing Medieval architecture. Recognized as UNESCO World Heritage Site since 1990, this city is a must see when visiting Tuscany. Step back in time and let your breath be taken away. Take pictures of this stunning city and savour some of the best Italian ice-cream.


Located in the heart of Tuscany, Siena is known to be one of Italy’s best preserved Medieval cities. During the Middle Ages it was one of the wealthiest independent states, after which it has experienced a few hundred years of poverty after its defeat by Florence in 1555. Being the home of one of the oldest universities of Europe, Siena has a vibrant, bustling atmosphere.

Interiors of Cappella Piccolomini, a masterpiece of Medieval art inside the Siena Cathedral
The walled Medieval city of Monteriggioni will surprise you with its architecture


Our third stop will take us to the beautiful castle of Monteriggioni. This completely walled Medieval town was built in the 13th century by the lords of Siena to control the Cassia Road, a major road that still runs just outside Monteriggioni. When there, take a step back and imagine living in this magical place during Middle Ages.


When in Tuscany, eat and drink like Italians do. The fourth stop of this tour will take us to a winery in the heart of Chianti. You will learn a lot about the history of Chianti’s famous wine, take a tour through the cellars and, of course, try some of the best wines of the region. The wine will be, obviously, accompanied with typical food for the most authentic Italian experience. Salami, prosciutto, cheese, olive oil… go and try them all!

A couple enjoying a visit to a vineyard during one of our Chianti wine tours

What's included

Private tour with personal service

Private tour with personal service


Free Wi-Fi on-board

Hotel pickup

Free pickup and drop-off (if located downtown)

Air conditioning

Transportation in air-conditioned Mercedes coach


All travel taxes and fees included

English speaking driver

Local English-speaking driver/guide with excellent knowledge of the destination

Champagne and prosecco wine

A bottle of prosecco wine and bottled water in each car


iPad mini with pre-marked points of interest, Wi-Fi and mobile data to bring with you during visits


Access to restricted traffic areas in all the towns

Prosecco Wine

Wine tour including wine and olive oil tasting with bruschetta and typical italian cured meat

Book Now