Chianti Wonders: Pisa, Siena and San Gimignano – Small group tour

A day trip to Pisa, Siena and San Gimignano with wine tasting: you will learn a lot about Tuscany’s rich history and art of wine.

Chianti Wonders are the towns San Gimignano, Pisa, Siena, and the Chianti wines such as the Chianti Classico. This day trip is perfect for those wanting to discover the Chianti region in a small group of max 8 people. A great way to explore Tuscany’s countryside.

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Starting from € 169 / Person
Tour duration

11:00 hours - Full day

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

Most travelers can participate
Mom with daughter caressing a baby board

A day trip from Florence for a small group. We will visit Pisa with its leaning tower, San Gimignano and its Medieval architecture, Siena with its narrow roads and a wine estate to experience some Chianti flavors. See new cities, explore new places while enjoying good food and fine wine.

Baby boar running in the countryside

Our first stop will be Pisa with its famous leaning tower. Then to San Gimignano, famous for its amazing Medieval towers and Italian ice-cream. Afterwards we will go to Siena, which is a definite must see when visiting the Chianti region. We will finish off the day in style by visiting a local winery where you will have the chance of taking pictures of Chianti wild life including wild boars. And remember: Italians never let their guests go home on a hungry stomach, so be prepared!

Tour Itinerary



Pick you up at your accommodation (hotel only, no Airbnb) if located in ZTL Zone A. Otherwise the meeting point will be Boccaccio Hotel, Via della Scala 59, Firenze (get directions)



First stop of 40 minutes to admire the amazing leaning tower of Pisa and take some pictures



Enjoy 50 minutes of free time to visit San Gimignano. Don’t forget to eat some of the best ice-cream Italy has to offer!



You will have 2 hours time in Siena to stroll through this Medieval city. Visit a museum, do some shopping, or have some food. The choice is yours!



We will finish off the day in style by visiting a local winery. You will enjoy a glass of wine and walk in their their estate with wild boars running all around and amazing nature.



We will be back to Florence before dinner time. But first we will have one last stop at Piazzale Michelangelo!


The Cathedral and Leaning Tower of Pisa


A stop of 40 minutes to appreciate the Leaning Tower of Pisa, which is a freestanding bell tower located in the city of Pisa in Italy. Like its name suggest, it actually does lean to one side. The tower started to lean during construction because the foundation was built on soft ground that had difficulty supporting the weight.


San Gimignano is characterized by the many towers that fill up the horizon, many Italians themselves visit this city as a day-trip due to its beauty. It lies just 56 km south of Florence and thus it is the perfect starting point for this full day Chianti tour.

San Gimignano skyline at dusk
Piazza del Campo in Siena


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!


The last stop of the day will take you to a winery: what better way to end the day with a glass of wine? Sit back, relax, and have some of the best flavors of Chianti. There you will learn all about Chianti’s rich wine history and also have a chance to take a walk into the Chianti wildlife and see wild boars, for some amazing pictures and memories. 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.

Grapes in a Chianti vineyard

What's included

Private tour with personal service

Small group tour with 8 people max


Free Wi-Fi on-board

Hotel pickup

Free pickup and drop-off (only hotel, if located in ZTL Zone A, no Airbnb)

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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