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

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
8 hours
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Number of Guests
1 - 8 guests
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Language
English, Spanish
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Other
Private Experience
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Digital Ticket
Mobile or paper ticket accepted

Explore Tuscany with a private tour from Florence. Visit Siena and San Gimignano, savor Chianti's scenic vineyards. Enjoy a personalized journey with hotel pickup and driver included.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

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 You Get

Wine Tasting Experience in a quaint Chianti Winery - if option selected
Air conditioning and USB charger on board
Independent Sightseeing in Siena, San Gimignano and Chianti Wine Region
Lunch
Local guides in San Gimignano and Monteriggioni

Good To Know

  • Please advise any specific dietary requirements at time of booking
  • Not recommended for travelers with poor cardiovascular health
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels

What You’ll Experience

1

Florence

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.
1 hourAdmission Ticket Free
2

Siena

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 hoursAdmission Ticket Free
3

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 minutesAdmission Ticket Free
4

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 minutesAdmission Ticket Free
5

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.
1 hourAdmission Ticket Free
6

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 minutesAdmission Ticket Free
7

Strada Statale 222 Chiantigiana

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 minutesAdmission Ticket Free
8

Strada Statale 222 Chiantigiana

Enjoy a personalized experience as a local producer guides you through the vineyards (not included in the tour price). You can discover the Chianti production secrets and ancient traditions which make this red wine so fantastic! After, there is no better way to finish your day than with an unforgettable Chianti Classico wine tasting accompanied by fresh, local products. Cheers!
15 minutesAdmission Ticket Not Included
9

Florence

Grab some bottles of Chianti Classico wine as souvenirs, take some final few photos of the spellbinding scenery, and then, your private driver will be ready to take you directly back to your accommodation in Florence.
1 hourAdmission Ticket Free

Meeting & Pickup

Pickup Point
Select a pickup point
Pickup Details
Your private driver will pick you up directly at your hotel or apartment's lobby

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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(114)
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Great views
July 01, 2025
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(TripAdvisor)

Great views! Amazing tour guide. Our bus driver on the other hand, coughed for the entire tour. Did not cover his mouth. Unlucky for me who sat right behind him, 3 days later got sick with the flu ...read more

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Beautiful view
June 30, 2025
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(TripAdvisor)

The views were spectacular and it was interesting to learn about the wine vineyards history. Our tour guide Cristian was very informative and did a great job of explaining the history of all the sq...read more

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A day in Tuscany
June 20, 2025
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(TripAdvisor)

Our guide Valentine was so nice and courteous and explained everything to us. He answered all of our questions too! He also recommended a beautiful winery to have lunch in. The views were incredibl...read more

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Absolutely Fantastic Tuscany Tour with Cristian!
June 16, 2025
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(TripAdvisor)

Our private tour to a Tuscany winery, Siena, and San Gimignano with Cristian was an absolute highlight of our trip! From start to finish, Cristian was incredibly knowledgeable, engaging, and genuin...read more

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Wondered experience touring with Ciaoflorence Tours
June 15, 2025
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(TripAdvisor)

Cristian was our tour guide and he was so enjoyable!! He explained everything so well and knew so much of the history. We listened to try to remember all of the info. He made our tour!!

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from  $906.54 
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Please note: The price varies based on group size. The time is in Central European Time.
Free cancellation (24 hours notice)
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INSTANT CONFIRMATION
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Earliest available date: July 14, 2025
from  $906.54  per guest
Book Now
Please note: The price varies based on group size. The time is in Central European Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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