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

143 Reviews 4.91 out of 5 stars Based on 143 traveler reviews collected by Cool Shore Excursions and TripAdvisor |
Recommended by 97% of reviewers
97% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Florence, Italy
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from $119.83 per person

Lowest Price Guarantee
Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region Image 1
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Don't miss out!
On average, this is booked 31 (0) days in advance.
8 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
and 1 more
Spanish
Instant confirmation

Overview

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

  • Air conditioning and USB charger on board
  • Independent Sightseeing in Siena, San Gimignano and Chianti Wine Region
  • Expert Professional Driver at your full disposal
  • Lunch
  • Local guides in San Gimignano and Monteriggioni
See 8 moreSee 8 more

Meeting and Pickup

Pickup point
Pickup details

Your private driver will pick you up directly at your hotel or apartment's lobby

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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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.
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1 hour Admission Ticket Free

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.
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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.
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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!
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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.
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1 hour 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.
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30 minutes Admission Ticket Free

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.
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15 minutes Admission Ticket Free

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!
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15 minutes Admission Ticket Free

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.
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1 hour Admission Ticket Free

Show 8 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-6367P30

Traveler Photos

Reviews

4.91
143 reviews

Average 4.91 out of 5 stars based on 143 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
135
4 stars
4
3 stars
3
2 stars
1
1 star
0
Don't miss out!
On average, this is booked 31 (0) days in advance.
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Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Cool Shore Excursions customers.

Filter by:

Q: What is the cancellation policy for the Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CET).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Air conditioning and USB charger on board.
  • Independent Sightseeing in Siena, San Gimignano and Chianti Wine Region.
  • Expert Professional Driver at your full disposal.
  • Commentary on board.
  • Tailor made Itinerary.
  • Wine Tasting Experience in a quaint Chianti Winery - if option selected1.
  • Photo Stops along the Way to portray the most beautiful landscapes of Tuscany.
  • Door to Door Hotel pickup and drop-off.
  • Dedicated office support available before, during, and after the tour to customize the experience.
  • Fully-fitted Mercedes vehicle with Free Wifi on board.
  • Direct access to the historic centre of UNESCO Listed Art Cities.
The following is NOT included:
  • Lunch.
  • Local guides in San Gimignano and Monteriggioni.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Air conditioning and USB charger on board
  • Independent Sightseeing in Siena, San Gimignano and Chianti Wine Region
  • Expert Professional Driver at your full disposal
  • Commentary on board
  • Tailor made Itinerary
  • Wine Tasting Experience in a quaint Chianti Winery - if option selected1
  • Photo Stops along the Way to portray the most beautiful landscapes of Tuscany
  • Door to Door Hotel pickup and drop-off
  • Dedicated office support available before, during, and after the tour to customize the experience
  • Fully-fitted Mercedes vehicle with Free Wifi on board
  • Direct access to the historic centre of UNESCO Listed Art Cities
  • Lunch
  • Local guides in San Gimignano and Monteriggioni

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • Please advise any specific dietary requirements at time of booking
  • A maximum of 8 people per booking

Report Product Issue

Activity name