Private tour to Siena, San Gimignano & Chianti
See the highlights of Siena, walk through the narrow streets of San Gimignano, admire Chianti wine country and visit a typical Tuscan winery.
from €640≈ $742 · £549Other currencies at today’s rate — you are charged in euro
- Location:
- Florence
- Duration:
- 9 hours
- Language:
- English
- Tour type:
- Private tour
- Group:
- Your party only
- Free cancellation:
- Up to 24 hrs
- Ticket:
- E-ticket on your phone
- Wine tastings included
- We collect you where you are staying
Why you will remember it
- Private is just for you! Top safety, comfort, privacy and flexibility
- Explore the medieval city of Siena
- See the magnificent Cathedral, the shell-shaped Piazza del Campo and much more
- Fall in love with the unique Tuscan landscape, driving through marvelous postcard views
- Visit a Tuscan winery and learn the local wine culture
- Enjoy a wine and olive oil tasting and other genuine products
- Stroll around picturesque San Gimignano famous for its medieval towers
- Enjoy a relaxing ride back to your accommodation
The itinerary
Explore the medieval atmosphere in Siena, San Gimignano and an ancient winery
See the highlights of Siena, walk through the narrow streets of San Gimignano, admire the beautiful Tuscan wine country and visit a typical Tuscan winery. All of this at your own pace and with the maximum comfort you can only get with a private door-to-door service.
SIENA
Start your private day with a scenic one-hour drive through the Tuscan countryside to reach Siena, the birthplace of the beloved Italian Saint Catherine.
Get lost in this beautiful city made of brown Siena-colored bricks (so that’s how they named the color!). A jumble of narrow streets and delightful squares, medieval towers that make such a spectacular skyline, the spectacular cathedral, the tall and trim Torre del Mangia.
All together create an enticing atmosphere almost like stepping back in time.
Piazza del Campo
Siena was built on three hills and is home to one of the most authentic and important Gothic cathedrals south of the Alps. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration having been seen in numerous films and photographs.
Palio horserace
In this brick-covered square twice a year takes place the famous ‘Palio’ horserace. It involves the entire population and is considered one of the most important events in the life of the local people. Almost anything will be done to win this extremely competitive race and bring home the ‘Palio’, a silk banner proudly displayed in the ‘contrada’ or neighborhood it represents.
SAN GIMIGNANO
Your private day trip will continue with a stop in San Gimignano. A small medieval town in Tuscany famous for its splendid skyline made up of 13 towers.
This 11th-century town rises 334 meters above Elsa Valley along the ancient road ‘Via Francigena’ on which traders and pilgrims traveled to Rome.
Ancient palaces and local crafts
Besides its remaining 13 towers, admire the Duomo and its magnificent frescoes, ‘Palazzo del Popolo’, ‘Palazzo Nuovo del Podestà’ today the town hall. See the church dedicated to Saint Augustine, the Museum of Holy Relics and the infamous Museum of Torture with its macabre displays of early torture instruments.
Wander up and down the main street in San Gimignano and enter the numerous specialty shops. The ceramics are beautiful here and there are also places for buying leather goods and linens.
CHIANTI WINE COUNTRY
Continuing the drive through amazing landscapes, reach the heart of Chianti Classico countryside. Stop at a hilltop winery for a visit at the discovery behind excellence then enjoy a tasting of the famous Chianti wine, olive oil and local food. The perfect way to conclude your experience and better understand the Tuscan wine culture.
At the end of your day in Siena, San Gimignano and Chianti, enjoy a comfortable relaxing drive to your accommodation in Florence
Private tour — everything you need to know
Included:
- Private service: your party will be the only one in the vehicle
- Free Cancellation up to 24 hours prior to departure
- Pick up and drop off directly at your accommodation in Florence
- Knowledgeable English-speaking driver to lead you through the experience
- Transport with fully equipped Mercedes vehicle, free Wi-Fi and fresh bottled water
- Free time to visit Siena at your own pace
- Free time to visit San Gimignano at your own pace
- Wine tour/tasting to a typical Tuscan winery
- All taxes, tolls and gasoline
- No hidden costs
Not Included:
- Entrance fees (if applicable)
- Meals
Optional:
- Gratuities
- Private local guide for 2 hours in Siena (Euro 250.00 per party)
- Wine tasting + light lunch at a Tuscan winery (Euro 70.00 per person)
- Extra hours to extend your day (Euro 90.00 per hour, per party)
Prices below are per party (not per person), vary depending on group size and are valid for pick up/drop off in Florence.
- Euro 640.00 – party of 1 person
- Euro 730.00 – party of 2 people
- Euro 820.00 – party of 3 people
- Euro 910.00 – party of 4 people
- Euro 1000.00 – party of 5 people
- Euro 1090.00 – party of 6 people
- Euro 1180.00 – party of 7 people
- Euro 1270.00 – party of 8 people
For different pick up/drop off locations, larger parties (9 or more people) or customized itineraries, please Contact us for alternative options for an estimate.
Tour type: private, your party will be the only one in the vehicle
Language: the driver is English-speaking
Vehicle: Mercedes sedan or van, depending on your party size
Activity level: easy
Accessibility: the experience can accommodate people with reduced mobility and foldable wheelchair/scooters users, if advised at the time of booking
Friendly cancellation policy: full refund for cancellations up to 24 hours prior to the departure time
Book With Confidence & Travel Safe: this tour is covered by our special Book with confidence and travel safe policy
Departure/Return point: your accommodation in Florence
Departure time: Suggested 9:00am but you can customize it to suit your travel needs
Service duration: The price includes up to 9 hours (i.e. 9:00am pick up – 6:00pm drop off). If you’d like to extend your day you can check availability directly with your driver.
Meeting instructions:
Hotel: your driver will look for you in the lobby of your hotel.
Private apartment: meet your driver close to the main door, in the street.
Any different meeting instructions will be notified on your confirmation voucher.
- 9:00am – Depart from your accommodation in Florence
- 10:00am – Arrive in Siena
- 10:00am to 12:00pm – 2 hrs, free time to visit Siena at your own pace
- 12:45pm – Arrive in San Gimignano
- 12:45pm to 2:45pm – 2 hrs, free time to visit San Gimignano at your own pace
- 2:45pm to 3:30pm – Drive through the Tuscan countryside
- 3:30pm to 5:00pm – Visit a Tuscan winery with a wine/olive oil tasting
- 6:00pm – Arrive at your accommodation in Florence
Please note: the schedule is to give an idea about distances, driving and sightseeing time. Being a private experience you can build your itinerary!
At the beginning of the day, your knowledgeable English-speaking driver will tell you all the feasible options to customize your experience and focus on the attractions/activities you are interested in.
If you prefer to plan everything, let us know your requests at the time of booking and we will create the perfect itinerary for you!
What our guests actually say
Every review below is public on the platform it came from.
Really enjoyed the beautiful landscape of the Chianti region. Together with the visits to San Gimignano and Siena make the sight and sound more complete and wonderful. The private tour to the winery estate top off a great day trip and fantastic experience. Awesome! I think if the overall duration of the day trip can be extended by one hour, it would be add on to the relax factor and more time to enjoy San Gimignano and Siena.
Our day was perfect. Giuseppe picked us up in a newer, nicely appointed E- Class Mercedes. He was prompt, professional, and very knowledgeable. The only thing that could have been better was if the car was an 8 cylinder model. Lol. We started with a ride through the country side to Siena, where we met with our tour guide that the companies up for us. She was very knowledgeable of the area and gave just the right amount of information without getting…
We had an incredible time. Our tour guide, Alessandro, was so knowledgeable about the area and shared so many interesting stories about the locations we visited. The wine tasting and tour was a highlight for me but cannot complain about any of the trip whatsoever. We highly recommend this tour to anyone visiting Tuscany and looking for a relaxing way to see the countryside and enjoy yourself!
Still not sure?
Ask us anything
A date that is not there, a pickup somewhere else, six people and a pushchair — if something does not fit, tell us and we will work it out. A person answers, usually within a few hours.
Have questions? Let’s chat!
Meet our native English-speaking experts, Violeta and Carrie. A different pick-up time, a second vehicle for a larger family, a licensed guide, a winery to add, a wheelchair to fit in the boot, a drop-off at the airport on your last day — tell them what your day needs to look like and they will build it.
Not sure yet?
Tell us what your day should look like
Private tours are built, not booked from a calendar. Send us the details and a real person answers — usually within a few hours.