Chianti’s Best – Small group tour

Siena, San Gimignano, Monteriggioni: the itinerary of this tour takes us to experience the many faces of the Chianti wine region

This Chianti tour is perfect for those wanting to discover the wine region at their own pace in a small group setting. You will learn more about the habits of locals, about Chianti’s long history. Eventually, you will come back home with a better understanding of Italy’s strong culture and history. And, of course, you will explore Tuscany’s famous cuisine and wine making traditions. Come with us to have a real taste of Chianti.

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Starting from € 149 / Person
Tour duration

09:00 hours - Full-day tour

Small group tour - Max 8 people in the VAN
Level: easy

Most travelers can participate
A girl is having a talk with a cat in San Gimignano: an encounter you can have while walking through the streets of San Gimignano

Siena, San Gimignano, Monteriggioni will be impressed in your memory with their magic Italian atmosphere. Visit them all with this tour and grab the essence of the Chianti wine region.

Piazza del Campo in Siena on a sunny day: its red bricks will be impressed in your memory

Leave the crowded streets of Florence behind you for a day trip in the Chianti region. San Gimignano will be our first stop. Known for its fascinating Medieval architecture, this small town will fascinate you with its relaxed atmosphere. Afterwards we will go to Siena, Italy’s best preserved Medieval city. With its narrow streets crowded with locals going about their daily business, Siena is definitely a must-see when visiting Tuscany. The third stop of this tour of Chianti will take us to the walled Medieval town of Monteriggioni, with its towers and walls, remnants of a stormy past. We will finish off the day in style by visiting a local winery where we will taste some wine and learn about the Chianti wine making process.

Tour Itinerary



Pick up at your accommodation (hotel only) if located in ZTL Zone A. Otherwise the meeting point is at the Boccaccio Hotel, Via della Scala 59, Florence (get directions) – Free cancellation up to 24 hours before the experience’s start time.



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



90/100 minutes to wander through the streets of Siena. You can visit a museum, do some shopping or have some food



30 minutes of time to explore the walled Medieval castle of Monteriggioni and imagine its turbulent past



Finish off the day in style by visiting a local winery. You will learn more about Chianti’s wine history and taste 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 first stop will lead you to San Gimignano, famous for its Vernaccia wine. This city summarizes the characteristics of the Chianti region. The many towers that fill up its horizon bear witness to the wealth of its ancient inhabitants. Italians themselves visit this city as a day-trip due to its beauty. San Gimignano lies just 56 km south of Florence, and thus makes it the perfect starting point for this full day Chianti tour.


Your driver will most likely advise you to go straight into the city center of Siena to see the Piazza del Campo. Due to its shell shape this square truly is one of a kind. From here you can also admire the Fonte Gaia, the largest fountain of the city made out of Carrara marble. You can also decide to climb to the top of the Torre del Mangia, or if you want to get really active: go for some shopping ;). It’s up to you.

A landscape showing the Siena skyline in a beautiful Sunny Day. Siena is the second stop of this tour of Chianti for small groups
The walled Medieval city of Monteriggioni will surprise you with its architecture


Can you really say you’ve visited the Chianti region without having visited Monteriggioni? This completely walled village in the Siena Province of Tuscany was built in the 13th century, and has even been cited by the famous poet Dante Alighieri in his most famous work “The Divine Comedy”. Every July the town helds one of the most well-known and beautiful events in the region: The Medieval Festival of Monteriggioni.


What better way to end the day with a glass of wine? Sit back, relax, and have some of the best flavors of Chianti. The last stop of the day will take you to a winery, where you will learn all about Chianti’s rich wine history. The knowledgeable staff of this wine estate will lead you around the property, explain you about the fermentation processes, show you the cellars, and let you taste some of the best wines out there.

At the winery you will attend a wine testing session of Chianti wines

What's included

Private tour with personal service

Small group tour with 8 people max This experience requires a minimum number of travelers.


Free Wi-Fi on-board

Hotel pickup

Free hotel pickup and drop-off (if located in ZTL Zone A)

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

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