Private Guided Day Trip Siena, San Gimignano and Chianti

5.0

Reviews

5.0 (6)

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5.0

Reviews

5.0 (6)

Earliest Date Available: September 24, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

Why book with byFood?

Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Earliest Date Available: September 24, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

Why book with byFood?

Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Location

Florence

Duration

8 hours

Group size

Max 6 guests

Accessibility

Stroller Accessible

Language

English, Italian

Location

Florence

Duration

8 hours

Group size

Max 6 guests

Accessibility

Stroller Accessible

Language

English, Italian

Why travelers loved this

5.0

•6 reviews

US$961.03 per guest

Instant Confirmation

Guest

Adult x1

Date

Add dates

Select Options

Earliest Date Available: September 24, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

Why book with byFood?

Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Earliest Date Available: September 24, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

Why book with byFood?

Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Description

Good to Know

• ESPERIENZA PER IL TUO GRUPPO PRIVATO • This GUIDED tour will take you in the morning to visit the city of Siena accompanied by an expert official guide. The afternoon will be dedicated to the discovery of the historical wine territory of Chianti. You will have the opportunity to visit some of the most famous vineyards, or small family-owned businesses, see their cellars and taste their excellent food and wines. Lastly, explore the wonderful medieval city of San Gimignano, considered one of the most beautiful historic Italian villages. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 9hr Full-Day private tour of Tuscany from Florence • Licensed TOUR GUIDE in Siena included • Visit the medieval cities of Siena, Monteriggioni, San Gimignano and Fonterutoli • Craft Chianti Classico wine at a local vineyard • Private transportation by Mercedes Minivan air-conditioned

Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
Departure is at 9:00am. Pick-up time can be changed upon request.
In case of rain, umbrellas will be provided by your driver.
A confirmation is appreciated the day before the appointment by e-mailing or via iMessage or WhatsApp.
This tour/experience is for a maximum of 7 travelers (your private party).
You will be picked up directly at your hotel or address (Florence down Town) provided at the time of booking at the exact time of the start of the tour.
Upon request, during the reservation we can organize lunch in winery, this is a highly recommended experience, especially for wine lovers. We also offer vegetarian and gluten-free lunches, and accommodate allergies. **Lunch in farm or winery (to be paid on-site from 55€pp to 65€pp)
*OPTIONAL FARM LUNCH (This option will exclude the possibility to visit the fortress of Monteriggioni).
Our drivers will happily assist with any questions or requests. They are vastly familiar with Tuscany and will share curiosities and facts, or offer suggestions about the area being toured, and more.

Panorama view photo stop

English-speaking licensed driver

On-board WiFi

WiFi on board

Private transportation by Mercedes Minivan Air-Conditioned

A licensed TOUR GUIDE in Siena 2/3hrs

Unlimited cold mineral water

Pick-up and drop off at your selected hotel/ location (Florence Down Town)

3 hours · Admission Ticket Free

Siena

Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore with your guide Siena’s rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts!

Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is on…

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Duomo di Siena

The Cathedral of Santa Maria Assunta is the main location of Catholic worship in Tuscany, and the diocese of Siena. The building is located in the square of the same name in the center of the city. Built in Italian Gothic style, it is one of the most significant and spectacular churches built in Italy.

The Cathedral of Santa Maria Assunta is the main location of Catholic worship in Tuscany, and the di…

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Piazza del Campo

Piazza del Campo (or simply, il Campo) is the main square of the city of Siena. Unique for its particular and original seashell shape, it is renowned all over the world for its beauty and architectural integrity, as well as for being the place where the Palio di Siena takes place twice a year.

Piazza del Campo (or simply, il Campo) is the main square of the city of Siena. Unique for its parti…

2 hours · Admission Ticket Free

Monteriggioni

Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants.

Make a lovely stop in the small, fortified village, which is still surrounded by its original mediev…

2 hours · Admission Ticket Not Included

Podere La Marronaia- Le Colonne Biodynamic Winery & Farm

*OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the way. Each of the four main courses and desserts will be paired with a different and distinctive glass of wine. We will conclude with ice cream and balsamic vinegar or other desserts.

*OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will…

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Strada Statale 222 Chiantigiana

The SS222 road, better known as Chiantigiana, is one of the most beautiful roads in Italy. It passes along the entire Chianti region, from Florence to Siena. Driving on it is a great way to discover the area. You will take this scenic road going north, starting from Siena and reaching Castellina in Chianti. The area is rich with castles and villages. One example is the Castle of Fonterutoli, where you will stop to admire the small medieval village surrounded by endless vineyards, centuries-old woods, and green hills.

The SS222 road, better known as Chiantigiana, is one of the most beautiful roads in Italy. It passes…

1 hour · Admission Ticket Free

San Gimignano

The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. Don't forget to stop by the famous Dondoli ice cream shop, winner of many awards for the best ice cream in the world. This is the last destination of the day, before returning to Florence

The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany.…

Pickup Point

Select a pickup point

Pickup Details

You will be picked up directly at your hotel or address communicated at the time of booking at the exact time of the start of the tour. Departure and pickup time is schedule at 9:00am. Upon request, you can change your pickup time (24hours before)

Free cancellation

Cancel up to 1 day before for a full refund.

No refund within 1 day of the experience or no-shows.

5.0

6 reviews

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6 reviews

Destination613702March 2026 • TripAdvisor

Tuscany tour at its best!

Remarkable Tuscany day trip! Alessandro is an amazing guide. Friendly, knowledgable and an excellent driver. The Tuscan countryside enroute to Siena was stunning. Rolling hills, olive trees and vineyards. Our first stop after leaving Florence was Siena. Siena cathedral is a stunning example of Gothic architecture. Built primarily in the 12th and 13th centuries, the cathedral is laden with black-and-white marble façade. Interior sculptures and paintings are everywhere. After a refreshing affogato...read more

sirwmoslerOctober 2024 • TripAdvisor

Superb Tour!

Our family of 6 adults took this day trip/tour with Alessandro in late October 2024. Everything about it was superb! Alex communicated with us after booking and as needed prior to our trip. Door to door service from our hotel, the tour was the right mix of necessary driving with plenty of time in Siena (including a terrific guided walking tour with an excellent local guide from Siena), San Gimignano, and we also chose the optional lunch at the winery which was great. Alex was passionate, knowl...read more

goofyk854June 2024 • TripAdvisor

Beautiful, peaceful and totally relaxing day.

This was a full day tour to the Tuscan countryside, including the towns of Siena and San Gimignano. Our guide, Alessandro Mascherini, is the best. He is knowledgeable, patient and soon seems like an old friend. He picked us up at the place we were staying and dropped us there at the end of the day. He arranged a wonderful lunch at a winery with lots of wine, olive oil and vinegar tasting. I reviewed that wonderful experience separately.

Lisa_KMay 2023 • Viator

Alessandro was super...

Alessandro was super helpful and informative. Made sure all our needs were taken care of and was a great guide for the day.

Zaid856August 2021 • TripAdvisor

Absolutely Amazing! Highly Recommended!

We did a private tour in Tuscany last week with Alessandro which was one of the highlights of our trip to Italy. At around 9:30 am, Alessandro picked us up from our Florence hotel in an air-conditioned Mercedes Benz Minivan. We then then proceeded to visit Siena which is lovely small town in Tuscany, then went on to Chianti on a spectacular drive through the many vineyards and olive farms. Chianti is the main wine region in Tuscany with beautiful landscapes. Alessandro was very knowledgeable abo...read more

Response from ViatorAugust 09, 2021

Hi Zaid! your review is really a pleasure to read, we spent a wonderful day, really a day spent with friends .. Hope to see you both again soon, again a big hug, we will see you soon in Dubai !! Alessandro

5.0 (3)

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Private Chianti Classico Wine Tour 8 hours from Florence

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Private Guided Day Trip Siena, San Gimignano and Chianti

Why travelers loved this

Experience details

Description

Good to Know

What's included

Itinerary

Siena

Duomo di Siena

Piazza del Campo

Monteriggioni

Podere La Marronaia- Le Colonne Biodynamic Winery & Farm

Strada Statale 222 Chiantigiana

San Gimignano

Meeting and pickup

Cancellation policy

All reviews

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