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

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Florence, Italy

From $320.09

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Safety measures
icon8 hours  (Approx.)
Hotel pickup offered
Mobile ticket
iconOffered in: English and 3 more
Good for avoiding crowds


Venture to the notable wine regions of Tuscany on this private day trip, departing from your Florence hotel. Your personal guide shows you around the medieval atmosphere of Siena and San Gimignano. Then, head to Chianti for an overview of this popular wine region. Pricing is per group, based on a maximum of eight people.
  • Tuscany tour from Florence
  • Visit Siena, San Gimignano, and Chianti, and enjoy free time at each stop
  • Private tour is operated with just your party and a driver
  • Hotel pickup and drop-off included
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Hotel pickup and drop-off
Mercedes vehicle
Speaking driver
Free time in Siena, San Gimignano and Chianti wine region
Bottled water
Local guides in San Gimignano and Monteriggioni
Wine tasting
Depart Florence in the morning with pickup from your centrally located hotel, and then settle in the comfort of your private vehicle during the drive to Tuscany. 

On arrival in Siena, spend some free time wandering the city's historical center. See the Piazza del Campo and the Italian Gothic cathedral at the Palazzo Pubblico. 

Leaving Siena behind for San Gimignano, you'll notice the pretty town's 13 towers from a distance. Relax as you amble past the weathered stone buildings and discover the town's hidden gems—it's an ideal place to purchase a meal accompanied by a glass of wine (own expense). 

Then set off for Chianti for more free time. If you choose, you can your a local winery and get a sense of traditional Tuscan life (own expense), and learn how wine is processed and produced.

Afterward, you're dropped off at your hotel in Florence.
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
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.
Duration: 2 hours 
Admission Ticket Free
Stop At:  
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.
Duration: 30 minutes
Admission Ticket Free
Stop At:  
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!
Duration: 15 minutes
Admission Ticket Free
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
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.
Duration: 30 minutes
Admission Ticket Free
Stop At:  
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.
Duration: 15 minutes
Admission Ticket Free
Stop At:  
Chianti Road
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!
Duration: 15 minutes
Admission Ticket Not Included
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Please advise any specific dietary requirements at time of booking
  • A maximum of 8 people per booking
  • Stroller accessible
  • Service animals allowed
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • No heart problems or other serious medical conditions
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate
  • OPERATED BY Ciaoflorence Tours & Travels Srl

For a full refund, cancel at least 24 hours in advance of the start date of the experience. Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on face masks and attendee health during Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
See all safety measures taken by Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region.
What is the policy on sanitization during Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region.
What measures are being taken to ensure staff health & safety during Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?
A:The policy on staff health & safety is:

  • Regular temperature checks for staff
See all safety measures taken by Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region.
What is the maximum group size during Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?
A:This activity will have a maximum of 8 travelers.

See all safety measures taken by Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region.

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42 Reviews

Reviews by Viator travelers

Showing 1-4 of 42 reviews
Awesome tour of sienna, San Gimignano & winerys
, Jun 2019
Our tour guide Christian was very knowledgeable about the sites & the wine! The private tour allowed us to customize our schedule. Would highly recommend spending a little extra $$ for this type of tour.
Best tour in Italy
, Jun 2018
We have taken many fabulous private tours in Italy but this was our favorite. Julian, our driver was full of history and knowledge. Siena and San Gimignano were wonderful but the real highlight of our trip was the visit the St Agnes Tuscany Winery which Julian arranged. Some of the best food and wine of the trip and we learned much about wine tasting.
The pros: Tuscany is beautiful and...
Teresa L
, Jun 2017
The pros: Tuscany is beautiful and the weather was amazing. The van was clean and we felt safe throughout the entire tour. We were traveling with my older father who uses a walker, and our driver was very accommodating in helping us load/unload and to drive him to the tops of hills/etc to limit walking. The short walking tour in Siena was great and we learned the most during this short walking tour which was led by someone in affiliation with our booked Viator tour. She was fantastic!!! The cons: There is a lot of ground to cover on this tour. Probably too much, especially when your driver takes you to two wineries without us asking to do so versus the published one expectation. I know... it sounds like we shouldn't be complaining - right? But, we rushed from place to place and were disappointed that we had such little time in Monteriggioni and San Gimignano. After returning home that evening, we re-read the tour description and learned why we were so rushed throughout the day - our driver had added a stop at an additional winery earlier in the day. When we arrived at this winery, we had no idea that is wasn't the one that was included in our package. He didn't tell us. The package says that a wine tour, tasting, and light food would be included in our winery stop. We assumed this was it. It wasn't. We certainly had sticker shock when we received our wine tasting and lunch bill that was 200e. We knew that lunch was not included in this tour, but we were ushered into this winery and assumed it was our included snack and tasting. We didn't order any food, it was simply brought out to us. Our stops in Monteriggioni and San Gimignano included 30-45 minutes of free time at each place. That's not even enough time to walk through the squares/etc. Very rushed. When we asked to just stay at San Gimignano for more time, we were told that we had already paid for the winery stop on the way home. So... this winery stop was the one we paid for. It did include the wine tasting and light food. We purposely picked this tour and it wasn't cheap so that we could see the area and enjoy the towns. If we wanted a multiple winery tour, we would have booked that. We spent about 3 hours total within Monteriggioni, Siena, and San Gimignano and the rest of the day was driving fast and rushed or spent at wineries. Minimal discussion about what we were seeing and the historical significance as we went from place to place. This was my parents first and most likely only trip to Tuscany so we were disappointed at the rushed experience throughout the day.
Wonderful tour, our driver Placido...
, Mar 2017
Wonderful tour, our driver Placido was great and gave us so much info along the way. We loved Sienna and San Gimignano. The wine tasting was so much fun!

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