Deep Wine Chianti and San Gimignano - Small Group Tour


€198.00 PP
Instead of €209.00 PP

Begin your exclusive journey with a dedicated 5% discount on all our Tours!

By scanning the QR Code, you’ve unlocked our exclusive discounted prices, the best available across all our platforms. So, congratulations! Let’s embark on a journey filled with countless memorable experiences with Truescany!

Join a scenic tour of the Chianti region and taste a selection of some of the best wines that Italy has to offer.

Come explore the Chianti wine region with us on a small group tour from Florence! You'll get to see some amazing landscapes and experience famous flavors while you're here.

We'll also have some leisure time to explore the charming medieval town of San Gimignano - famous for its city of towers, and of course, the best ice cream in the world! Your guide will be more than happy to give you some helpful pointers along the way.

We'll also visit two local wineries for tours, followed by a tasting of renowned Chianti varietals. And of course, no Tuscan experience would be complete without a traditional Tuscan lunch!


Piazzale Michelangelo: You won't believe the view you get from the top of this square in Florence.

San Gimignano: Explore the walled city for a memorable experience full of history, culture and charm

San Casciano in Val di Pesa: Enjoy a delicious lunch with the best wines of Italy

Local Food: Savor locally made products like cheese, salami and olive oil

San Michele a Torri: You will visit a family-run organic wine estate where you can try other excellent Chianti wines

FROM €209.00

Price per person

Full day TOUR

9 Hours (approx)

small group

Max 8 in a Mercedes van


From selected hotels

Why You’ll love this tour

This tour is the perfect way to experience all that the Tuscan region has to offer in just one day. You'll be able to admire stunning panoramas of vineyards and olive groves, and sample some of the best Chianti wines in the world. And what could be more delicious than fresh, local Mediterranean cuisine?


We loved the little towns we visited. The owner of the winery was very generous and hospitable. We could see his passion in his work. He was casual, and this created a fun, relaxing environment. To us the prices of the wine and shipping was very reasonable. I believe one of the main highlights for us was the driver Andrea. We enjoyed his stories and his charisma. Totally would recommend him!

by Frank_M


Piazzale Michelangelo

We start from the pick-up point at 8:00 am and then drive for 15 minutes towards Piazzale Michelangelo, a stunning panoramic view spot in Florence. From this elevated terrace, you can see all of Florence’s top attractions without any of the city’s traffic. This is a must-see spot for tourists and locals alike who want to take in the beauty of Florence. From here, you can really appreciate all that the city has to offer. The large square is home to a replica of Michelangelo’s David in bronze.

Duration: 15 minutes
San Gimignano

We’ll drive to reach San Gimignano, a beautiful walled city. The drive will take approximately one hour and we’ll arrive at 9:30 am. 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.

Duration: 1 hour 25 minutes
San Casciano in Val di Pesa

We’ll drive for 50 minutes towards a typical Tuscan farmhouse in the Chianti area. We’ll take you on a trip to the stunning Tuscan wine country, where you’ll get to experience delicious wine tasting and lunch amidst the incredible views of the Tuscany countryside. You’ll visit a beautiful farmhouse with amazing cellar, and enjoy some of the most famous wines in Italy while indulging in a delicious lunch made with local ingredients. It’s time for you to sit back, relax, and enjoy the view—we can’t wait to show it all off!

Duration: 2 hours 30 minutes
San Michele a Torri

We’ll drive for 25 minutes towards San Michele a Torri where we’ll arrive at 3:00 pm. We’ll cap off our journey at a family-run organic wine estate in the province of Florence, where you’ll get to try some other superb Chianti wines. After all, you can’t really say you know Chianti until you’ve tried at least 5 or 6 different types of wine from the area.

Duration: 75 minutes

We’ll drive back for 40 minutes to reach the initial pick-up point at 5:00 pm and you’ll have plenty of time to enjoy the rest of your afternoon in Florence.

Duration: 40 minutes

What’s Included and what's not

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)
4 Wine tasting and olive oil tasting
Wine tasting and olive oil tasting
Wine tour with cellar visits
Entrances to museums, castles and villas

Meeting point

You can head directly to the meeting point, or request pickup. Meeting point Hotel Boccaccio in Via della Scala, 59, 50123 Firenze FI, Italy.

The tour starts at 08:00 am. Please show up at the meeting point 15 minutes in advance.

Pickup details

We offer free pick up at hotels, not Airbnb nor apartments, located in AREA A of the traffic limited zone.

If your hotel is outside that area or falls in the category of Apartments/Airbnb, you can choose to receive free pick up in front of:

Hotel Boccaccio (Via della Scala 59) at 08:00 am
Hotel Davanzati (Via Porta Rossa 5) at 07:50 am


Please click here to check if your hotel is located within Area A.


If your accommodation is situated beyond Area A of the restricted traffic zone, we kindly ask that you inform us upon booking your tour. This will allow us to provide you with a tailored quotation to best suit your needs.


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

It’s important to note that regardless of age, the full price of a small group tour must be paid by all participants, including young children.


  • For a full refund, you must cancel at least 24 hours before the experience’s start time. 
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded. 
  • Any changes made less than 24 hours 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.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Top benefits of booking directly with us

what they say about us

We loved the little towns we visited. The owner of the winery was very generous and hospitable. We could see his passion in his work. He was casual, and this created a fun, relaxing environment. To us the prices of the wine and shipping was very reasonable. I believe one of the main highlights for us was the driver Andrea. We enjoyed his stories and his charisma. Totally would recommend him!

by Frank_M

Fabio was a fantastic guide with lots of knowledge. A great tour for people who want to see Tuscany. Beautiful towns, incredible countryside and ended with a brilliant wine tasting. Highly recommend

by Tom_E

This was a wonderful tour, a lot more than we expected. Our driver Daniel was very knowledgeable of sights, history, and wines that went with certain foods. His recommendation if it was on our to do list was Chianti Classico with a steak ❤️❤️ We highly recommend this tour and Daniel.

by debihair13

Our tour guide was personable, knowledgeable and entertaining. We were part of very small group and felt that all got very personal attention. The wine tasting and tour of the winery was great. And the wine, snacks more like a small meal were wonderful as was the hostess at the winery. Would recommend it to friends and family and will when any of them visit Florence

by Douglas R

We could not have enjoyed our day more! Our driver was knowledgeable and friendly. The three stops were perfect, broke up the ride so we never felt we were in the car too long. We were lucky to be joined by a nice couple as well. The winery was lovely. It was a beautiful day!

by Marie M

Our guide Amiiano was excellent. He was extremely knowledgeable about the area and its history. He was down to earth and friendly. It felt like we were spending a nice day with friends (4 tourists + Amiliano). At every stop, he gave us iPads that had pre=programmed areas of interest on the map so we can be efficient with our exploration. At the end of our tour, Amiliano even busted out a bottle of Prosecco for us to share and toast to a great day.

by bhwang111

book this tour


Begin your exclusive journey with a dedicated 5% discount on all our Tours!

*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.


Thinking of leaving?

Get an exclusive 10% discount on all tours by joining our newsletter now! Stay updated and save big!

Add Your Heading Text Here

Choose your car
CARD year *