Private Guided Day Trip Siena, San Gimignano and Chianti
Traveler rating
5.0/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Guided Day Trip Siena, San Gimignano and Chianti worth booking?
Private Guided Day Trip Siena, San Gimignano and Chianti is a 8-hour experience in Florence, Italy, from $492 per person. It scores 59 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 59 / 100
- Rating
- 5/5 (6)
- Duration
- 8 hours
- From
- $492 per person
• 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
What you get
About this experience
• 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
What's included
Included
- Panorama view photo stop
- English-speaking licensed driver
- On-board WiFi
- 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)
What you'll see and do
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!
180 minutes here
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.
Pass by without stopping
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.
Pass by without stopping
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.
120 minutes here
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.
120 minutes here · Admission not included
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.
Pass by without stopping
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
60 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- UNIQUETUSCANY private tours
Know before you go
- 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.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.
The guide
5 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
5 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
6 verified traveler reviews for Private Guided Day Trip Siena, San Gimignano and Chianti. Ratings and reviews provided by Viator and 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, we headed to San Gimignano first stopping for lunch and wine tasting at Tenuta Guardastelle. Nothing short of spectacular and picturesque with amazing wines. Next stop was inside the walls of San Gimignano, a perfect example of a Tuscan medieval city. Lots of shopping for salami's, pecorino, leather and of course gelato. A fantastic tour for sure all thanks to Alessandro. Gratzie!
via 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, knowledgeable and a pleasure to spend time with. He did the little things that made the trip more enjoyable, like letting us know where to get the best views and where to get "the worlds most famous gelato!" As an added bonus, he gave us a great dinner recommendation and contact information that made getting a water taxi in our next stop (Venice) easy! This day was one of the highlights and possibly the most enjoyable day of our two week trip to Italy! Thank you Alessandro!
via 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.
via Tripadvisor
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.
via Viator
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 about the area and the wine industry. We opted for a lunch at a local farm (and winery) which was truly amazing and highly recommended. We got to sample different types of homemade foods and various local wines. After lunch, we drove through some small and super charming Tuscan villages where we made couple of stops to explore the area. Again, Alessandro was very knowledgeable and went out of his way to give us a lot of valuable and interesting information about the area and these little towns. We then went back to Florence and were dropped back at our hotel. All in all, this is a fantastic trip and great value for your money. Uniquetuscany and Alessandro are your perfect partners for your day trips in Tuscany.
Response from the operator: 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
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $492 to $850
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Who runs this experience
Operated by UNIQUETUSCANY private tours, who run 6 experiences we rank across 1 city, with an average Outty Ranking of 58.9.
See everything UNIQUETUSCANY private tours runsWhy this scores 59
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Guided Day Trip Siena, San Gimignano and Chianti: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Guided Day Trip Siena, San Gimignano and Chianti cost?
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Prices start at $492 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Guided Day Trip Siena, San Gimignano and Chianti take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is Private Guided Day Trip Siena, San Gimignano and Chianti worth it?
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It holds an Outty Ranking of 59 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Guided Day Trip Siena, San Gimignano and Chianti?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Guided Day Trip Siena, San Gimignano and Chianti suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Guided Day Trip Siena, San Gimignano and Chianti?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Private Guided Day Trip Siena, San Gimignano and Chianti start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Private Guided Day Trip Siena, San Gimignano and Chianti?
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Included: Panorama view photo stop; English-speaking licensed driver; On-board WiFi; Private transportation by Mercedes Minivan Air-Conditioned; and A licensed TOUR GUIDE in Siena 2/3hrs. Always check the voucher for the final list before you travel.
Does Private Guided Day Trip Siena, San Gimignano and Chianti include hotel pickup?
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Yes, pickup is offered for every traveler from 415 listed pickup locations in and around Florence. You can also enter a custom pickup address when booking.
What languages is Private Guided Day Trip Siena, San Gimignano and Chianti offered in?
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It is offered in English and Italian. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Guided Day Trip Siena, San Gimignano and Chianti?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Guided Day Trip Siena, San Gimignano and Chianti wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Guided Day Trip Siena, San Gimignano and Chianti if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Private Guided Day Trip Siena, San Gimignano and Chianti?
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Across 6 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works.
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