Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

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From $369.43

63 reviews   (4.49)

Price varies by group size

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Pricing Info: Per Person

Duration: 8 hours

Departs: Florence, Florence

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

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Enjoy a day away from Florence as you visit Siena, San Gimignano and the picture-postcard Chianti area. Take your time to appreciate everything Tuscany has to offer. Enjoy the personalized attention of your private driver and breath in the Medieval atmosphere surrounding Siena and San Gimignano, two authentic jewels nestled in the heart of Tuscany. On the way back to your hotel in Florence, enjoy breathtaking views of the gentle hills and vineyards of the Chianti wine region. Hotel pickup and drop-off and a driver is included.

What's Included

Bottled water

Free time in Siena, San Gimignano and Chianti wine region

Hotel pickup and drop-off

Mercedes vehicle

Speaking driver


What's Not Included

Local guides in San Gimignano and Monteriggioni


Wine tasting

Traveler Information

  • ADULT: Age: 0 - 99

Additional Info

  • Infants and small children can ride in a pram or stroller
  • Not recommended for travelers with poor cardiovascular health
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Infants and small children can ride in a pram or stroller
  • Not recommended for travelers with poor cardiovascular health
  • Public transportation options are available nearby
  • Specialized infant seats are available

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.

What To Expect

Prepare for a day of absolute bliss as you discover the best of Tuscany… A private driver will pick you up directly from your accommodation in the comfort of a luxury Mercedes vehicle. Simply relax and enjoy the beautiful rolling hills throughout your journey from Florence to Siena. You will arrive there in about an hour.

60 minutes • Admission Ticket Free

Upon arrival, your driver will drop you off very close to the Siena Cathedral, a major perk of traveling privately! Siena breathes history, and it is the hotspot of medieval glory throughout the Tuscany region. With a rich past of architecture, art, and culture, the city of Siena itself is a UNESCO World Heritage Site! Enjoy two hours of independent exploration throughout the medieval-style buildings, artisanal shops, local restaurants, and picturesque alleyways.

2 hours • Admission Ticket Free

Piazza del Campo
As you follow the picturesque streets of Siena, it is impossible to miss the most famous square in the city - Piazza del Campo. This (very) large, oval shaped piazza is a popular place for locals to gather with family, friends, and classmates. You will find plenty of Sienese locals resting on the wide slopes, which lead to Palazzo Comunale and Torre del Mangia. It is also home to an annual palio horse race, which is an epic competition between the different neighborhoods of Siena! After admiring the panoramic views, re-energize yourself with a cappuccino at one of the many cafes lining Piazza del Campo, experiencing Siena as the locals do.

30 minutes • Admission Ticket Free

Duomo di Siena
After spending some time leisurely exploring the city, it will be time to visit the beating heart of Siena - the Siena Cathedral. The breathtaking facade is decorated in pink, green, white, and black marble. Constructed in the 1200’s, this is a marvelous example of Romanesque-Gothic architecture. After entering, admire the uniquely carved marble floors, which depict biblical stories on 56 different scenes. As you look up, you will see masterpieces throughout the church from Renaissance masters including Donatello, Pisano, Pinturicchio, and Michelangelo. Stroll through the grandiose atmosphere inside, and before exiting, don't miss the hidden gem of the Cathedral - the vividly painted Piccolomini Library!

15 minutes • Admission Ticket Free

San Gimignano
Then, hop back in your luxury, private vehicle, and you will be on your way to the nearby town of San Gimignano. As you get closer to the hilltop town, your driver will gladly point out its unmistakable medieval “skyscrapers.” Sometimes called a medieval Manhattan, there are still thirteen towers intact in this perfectly preserved hilltop town. Your driver will drop you off outside the ancient gate of the city. Here, you can find a famous panoramic viewpoint of the Tuscan countryside and its rolling, green hills filled with olive groves and vineyards. You will have an hour to explore the lovely, Renaissance town of San Gimignano as you please.

60 minutes • Admission Ticket Free

Piazza della Cisterna
As you wander through the characteristic alleyways of San Gimignano, the streets will lead you to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and striking medieval architecture! Indulge in a local a gelato or coffee, and enjoy the lovely views of this ancient city.

30 minutes • Admission Ticket Free

Chianti Road
When you are finished exploring San Gimignano, your driver will be at your service! You will be on your way to the world-renowned Chianti region, with its truly magical landscapes. Admire the marvelous scenery, dotted with tiny villages and magnificent castles dominating the sunny, rolling hills. One of the perks of a private tour is the ability to make stops whenever you see something that catches your eye! Simply ask, and your driver will be more than happy to allow you to take some wonderful photos.
Make the most of your time in the famous Chianti wine region with a local wine tasting! You have the option to make your own reservations at a wine estate, we are happy to do the planning for you, or your driver can even help with recommendations! If our optional wine tasting is added to your itinerary, your driver will take you to a local wine estate in the heart of the Chianti hills.

15 minutes • Admission Ticket Free

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