Chianti's Best - Tour by night


€170.00 PP

Take in the rolling hills and beautiful sunsets of Tuscany and end your day with a wine tasting and dinner at a local winery.

Uncover the secrets of the Tuscan countryside on this private tour! In the afternoon, you'll explore the rolling hills and beautiful sunsets of Chianti region. As you drive through wine country, your expert guide will share fascinating insights about Italy's culture. You'll visit world-famous landmarks in San Gimignano, Monteriggioni, and Siena—and end your day with an unforgettable winery tour, tasting session with gourmet lunch, and a traditional Tuscan dinner.

FROM €170.00

Price per person

Full day TOUR

9 Hours

Private Tour

Max 8 per Mercedes van


From selected hotels

Winery: Enjoy a wine tasting at one of the best wineries in town

San Gimignano: Explore the city famous for its many towers, astonishing Medieval architecture and taste the best ice cream in the world!

Monteriggioni: Visit a walled Medieval village built during the 13th century

Siena: Discover Italy's Historic Gem

Restaurant: Have Dinner in a Typical Tuscan Restaurant

A day full of food, wine, and amazing scenery sounds like the perfect way to spend a day in Tuscany. The Chianti's Best by Night full day tour is designed for those who want to truly experience all that Tuscany has to offer. You will visit San Gimignano, Monteriggioni, Siena, a winery and our Italian restaurant while your private driver gives you interesting information about the region and tips on where to go and what to avoid while visiting the cities.


Highest average rating based on over 2.000 reviews


Highest average rating based on over 2.000 reviews

I booked I Just Drive through the Hotel Davanzati and selected the Tuscan Countryside package which included a drive to several cities. We visited Piazzale Michelangelo, San Gimignano, Siena, Monteriggioni and a stop at Montespertoli Vineyard for a wine tour. Our driver was Fabio and he was an excellent guide – he was very knowledgeable of the towns, shared the history of the towns along with “legends” of the towns. If you are thinking about booking a trip through I Just Drive (Now Truescany), I urge you to do so – you won’t be disappointed. Thanks for making the trip to the Tuscan countryside memorable, Fabio!

Mason M



We start from your pick up point at 02:00 pm and then drive for 50 minutes to reach the winery.

Duration: 45 minutes

It’s 3:00 pm and it’s hard to imagine a better way to start off the afternoon than by trying some fine wines and typical Italian side dishes. Also try some of the best olive oil and vinegar of the region. The knowledgeable staff of this family-owned winery will give you a private tour of the wine estate and explain all about how they produce their amazing wine.

Duration: 1 hour

At 05:00 pm you will arrive in San Gimignano ready to explore the beautiful walled city. San Gimignano is a town that is oozing with history and charm. It’s well-known for its delicious ice cream and impressive stone towers. These towers were built during medieval times and served as a form of defense. Of the 72 towers that once stood, 14 remain today – a testament to their strength and durability. In 1990, the town’s center was declared a UNESCO World Heritage site. Forget about all of your worries for a moment and savor a delicious ice cream when visiting San Gimignano. This city is known for having some of the best ice cream in Italy, so you’ll be sure to enjoy your sweet treat. Let the creamy goodness Melt in your mouth and transport you to a world of pure bliss.

Duration: 30 minutes

At 6:00 pm you will be visiting the picturesque town of Monteriggioni in all its splendor. Monteriggioni is one of the oldest, most memorable and recognizable villages in all of Italy, and it seems that it has been inhabited since the eighth century BC. It’s a true jewel for anyone who wants to dive into the Middle Ages. Monteriggioni Castle is a fascinating place with a rich history. It was founded in the 1220s by the Republic of Siena to protect against Florence. Today, it remains much as it was in the 13th century, with famous city walls and 14 towers. From the top of the hill, you can enjoy a beautiful panorama of Siena.

Duration: 20 minutes

At 6:45 pm we’ll visit Siena. With its harmonious medieval architecture and idyllic backdrop of arable fields and rolling hills, it’s no wonder that Siena has been able to maintain its unique charm for centuries. When you visit Siena, you feel as though you are stepping back in time to a place where the only thing that matters is the present moment. Siena is a city rich in art and history, with many treasures to be found both in its museums and on its streets. Piazza del Campo is one of the most famous and beautiful squares in Italy, and every year it plays host to the Palio delle Contrade, a spectacular horse race.

Duration: 1 hour 25 minutes

At 8:30 pm we are ready to have dinner in a typical tuscan restaurant. After this day full of new experiences, you will finish off the day with an explosion of flavors at our traditional Italian restaurant. Enjoy a selection of fresh cuts, typical Tuscan cheeses and prosciutto. You’ll have plenty to talk about after this day full of new experiences.

Duration: 1 hour and 30 minutes circa

11.00 pm we’re back in Florence

Local English-speaking driver/guide with excellent knowledge of the destination
Free Hotel pickup and drop-off (in selected hotels)
Pickup and drop-off from designated meeting points
Luxury Mercedes Vehicle
WiFi on board
Air-conditioned vehicle
Bottled water
1 Bottle of Prosecco White Wine per group
Wireless audio system to better hear the driver even from the last rows
1 iPad each couple (with unlimited mobile data connection)
Tuscan dinner in a typical restaurant
Entrances to museums, castles and villas

As part of our commitment to providing a stress-free and comfortable experience for our guests, we offer pick-up at your location within the downtown area of Florence for our private tours. If you are unsure whether your location falls within this area, please let us know in the dedicated section at the time of booking and we will be happy to assist you. Our goal is to ensure that your tour with us is seamless and enjoyable from start to finish.

Stroller accessible

Infant seats available

Confirmation will be received at time of booking
A maximum of 8 people per Mercedes van
The driver/guide will thoroughly introduce the places being visited, from a cultural, historical and artistic viewpoint while driving to and from them, but is not licensed to give explanations at sights or guide inside churches, or museums.You will have free time in the villages
  • For a full refund, you must cancel at least 8 days before the experience’s start time. 
  • If you cancel less than 8 days before the experience’s start time, the amount you paid will not be refunded. 
  • Any changes made less than 8 days before the experience’s start time will not be accepted.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Wonderful way to see San Gimignano, Monteriggioni, Sienna and a wine tasting all in one afternoon. Our driver Fabio was excellent !!! Beautiful views from a comfortable Mercedes sedan. This company is very well run and easy to navigate the informative website.


I visited Florence with my parents and sister to celebrate my folks 50th wedding anniversary. My father’s mobility can be challenged, and going with I Just Drive to see the countryside was a perfect solution for us. We booked two tours, the communication was excellent, the drivers extremely punctual and professional while being fun, and the cars were very luxurious and comfortable. I highly recommend this company. We did the Deep Chianti tour, along with a gentleman from Japan, hosted by Daniel. It was a great time! Daniel was informative and fun, and the wineries we visited were excellent. Both offered excellent tours, information, wine and olive oil, charcuterie and cheese (and one was on an amazing property with a “summer house”). You definitely won’t be hungry so don’t eat a lot at lunch! Day two we did the Best of Tuscany with four other people from New Zealand, hosted by Fulvio. He also was very knowledgeable and fun. We saw San Gimignano, Monteriggioni, and Siena which were all very beautiful. Unfortunately, it was raining on and off all day, but we had umbrellas and made the best of it – it was still beautiful! We also visited a winery that was very good and informative with good prices as well. It was a good day.


This was our first trip to Italy and we truly enjoyed our day trip from Florence out to see parts of Tuscany including San Gimignano, Monteriggioni, Siena and a winery. Our driver, Fulvio, was super-friendly, fun and full of information about the places we were visiting. It was a nice change of pace from the museums and monuments we had seen thus far on our trip and a chance to experience the countryside and some smaller, slower-paced and very beautiful towns.

Joanna R

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*Best discount negotiated on certain dates, calculated according to the supplier reference price.


From Monday to Sunday from 8:00 a.m. to 8:00 p.m. Local call charges may apply.


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