Private Tuscany Tour: Siena, San Gimignano & Chianti
About this activity
Highlights
- Explore Siena's historic center
- Visit San Gimignano's medieval towers
- Enjoy Chianti wine tasting
- Discover Tuscan countryside landscapes
- Experience authentic Italian culture
Full description
Included / Excluded
- Private transportation from Florence
- Guided tours of Siena and San Gimignano
- Wine tasting in the Chianti region
- Meals and beverages not specified
Itinerary
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.
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.
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.
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!
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.
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.
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.
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!
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.
Important information
Know before you book
- Confirm the tour date and time at least 24 hours in advance.
- Provide any dietary restrictions or preferences when booking.
- Be aware that some sites may have entry fees not included in the tour.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture scenic views and historic sites.
- Check the weather forecast and dress accordingly.
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Service Animals Allowed
- Easy Public Transport
- Infants Required On Laps
- Infant Seats Available
Good to know
- Please advise any specific dietary requirements at time of booking
- A maximum of 8 people per booking
Traveler reviews
Fantastic day trip!
Fantastic day trip! Our driver Valentin was the best! He arrived at our hotel in a beautiful Mercedes Benz. As he drove us to each city, he provided a brief history about where we were going to visit. At each city we had plenty of free time to roam around and enjoy. Our last stop was the winery. We had a wonderful time sipping the various wines. However, when we were given the last wine to taste, the waitress didn’t even allow us 5 minutes to enjoy it. She said “let me guide downstairs as your hour is up”. To be honest, we would never do the wine tasting again. We felt they cared more about selling wine than allowing the guest to have a nice experience. Overall, we give it 5 stars because of Valentin and the beautiful cities we visited but not the wine tasting.
Tuscany highlights
Our tour with guide, Cristian, exceeded our expectations. Not only was the scenery wonderful, Cristian was enthusiastic, knowledgeable and tailored the private trip to our needs. We enjoyed the experience to such a degree that we had Cristian again for another tour two days later. Bruce S and Ann H, Vancouver, Canada
We were on a 2-1/2 week...
We were on a 2-1/2 week vacation and this was by far one of the best experiences we had. The countrysides are beautiful and mostly breathtaking. Our drive (Valetine) was awesome - friendly, knowledgeable and informative. The cities we visited (Siena and San Gimignano), as well as the ChiantiWinery were all fantastic! I would definitely recommend this tour!
The Chianti Experience
Cristian was a fantastic tour guide. A lot of information and great recommendations for the group. He picked out a great spot for lunch at a small family winery. Totally worth the experience and would recommend to anyone visiting the Florence/Tuscany region. We had so much wine and food! 10/10!
Wow
Was absolutely stunning Milko was our driver . Such a lovely person We enjoy all the ride with him I surely recommended to do this tour