Private Day Trip Siena, San Gimignano and Chianti from Florence
Traveler rating
5.0/5
Based on 269 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Day Trip Siena, San Gimignano and Chianti from Florence worth booking?
Private Day Trip Siena, San Gimignano and Chianti from Florence is a 8-hour experience in Florence, Italy, from $390 per person. It scores 84 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 5/5 rating across 269 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 84 / 100
- Rating
- 5/5 (269)
- Duration
- 8 hours
- From
- $390 per person
• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena, San Gimignano. Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside. Upgrade your experience with an optional wine tasting or an optional traditional lunch at a local organic farm or winery. • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the winery by your guide • Taste Craft Chianti Classico wine at a local vineyard (option) • Hotel or private address pick-up & drop-off Perfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.
What you get
About this experience
• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena, San Gimignano. Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside. Upgrade your experience with an optional wine tasting or an optional traditional lunch at a local organic farm or winery. • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the winery by your guide • Taste Craft Chianti Classico wine at a local vineyard (option) • Hotel or private address pick-up & drop-off Perfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.
What's included
Included
- English-speaking licensed driver
- On-Board WiFi
- Unlimited cold mineral water
- Free time in Siena and San Gimignano
- Private transportation by MiniVan, Air-Conditioned
- Pick-up and drop-off at your selected hotel/location (in Downtown Florence)
What you'll see and do
Siena
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 its 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!
120 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.
90 minutes here
Marronaia Wine Garden
*OPTIONAL lunch at an organic winery. Have lunch at a wonderful organic/biodynamic farm/winery in a beautiful setting overlooking the medieval towers of San Ginmignano. Enjoy a unique culinary experience while admiring an extraordinary Tuscan panorama among olive trees and vineyards. You will taste organic specialties, such as typical fresh pasta with traditional sauces, crostini, local meats and cured meats, legumes, seasonal vegetables, honey and cheeses seasoned with an incredible balsamic vinegar. The wine "Super Tuscan, Chianti, and Vernaccia" will accompany this lunch at every stage of the journey. Each of the four main courses and dessert will be paired with a different and distinctive glass of wine. We will conclude with a fabulous dessert. Allergies or special diets will be handled without problems by the company, upon your request at the time of booking. (This option will reduce a little the time in the cities of Siena and San Gimignano and will exclude Monteriggioni Fort).
120 minutes here · Admission not included
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.
90 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
- In case of rain the umbrellas are provided by your driver.
- Kindly share your mobile number for an easy communication during the pickup
- This tour/experience will have a maximum of 6 travelers (your private party).
- With agreements during the reservation we can organize lunch in winery, this is a highly recommended experience, especially for the wine lover. Dedicated lunches for people with cilia, allergies or vegetarians. (This option will exclude the possibility to visit the fortress of Monteriggioni). **Lunch in winery available (as an option on request) at an extra cost 55€pp to 65€pp per person. **
- Departure is suggest at 9:00am. Pick-up time can be choise during the reservation
- Authorized guide not included
- Minors under 18 years old are not allowed to drink alcohol (wine tasting)
Photos
What travelers are saying
Outty’s summary of the themes that recur across 269 traveler reviews. Written by us, not quoted from reviewers.
The guide
6 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.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
269 verified traveler reviews for Private Day Trip Siena, San Gimignano and Chianti from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Tour in the Tuscan Countryside in One Day
Delightful day with friends riding along with Alessandro.he picked us up outside our apartment . Alessandro was an excellent guide and driver. He dropped us off at planned points and picked us up at a designated area. It was very easy. We travels to three towns. We were given fabulous tips. He chose a wonderful restaurant that offered an excellent selection of gluten-free items, as well as, delicious food and wines. We had a beautiful day.
via Tripadvisor
The best!
Excellent! Highly recommend! Allessandro is outstanding. Every step of the process from the first contact to the tour was highly professional, warm, responsive. Took us to all the best places. Excellent conversation. No hidden costs. Very engaging personality. Lovely car, very comfortable.
via Tripadvisor
Fabulous day in fabulous Tuscany
As with most tours, the success of the tour depends on the tour guide and Carlos didn’t disappoint . He was very knowledgeable about wine and the absolutely gorgeous countryside of Tuscany. He was very entertaining and also very aware of his audience and the type of wine we would enjoy. So, at the third winery he took the owner aside and suggested she change the menu of wines we were going to taste. It was a success because the owner sold a lot of delicious wine that day. Not sure if I should mention the winery , Castlevecchio, but the views of the patio were spectacular. After the first winery we had a delicious on an outdoor pastry with another view of the valley. Definitely recommend the 3 winery tour.
via Viator
A Perfect Day!
This was a wonderful day! Don’t miss the winery lunch- delicious!! We all love every minute of the tour! Great driver too!
via Viator
Tuscany Dream
This was a wonderful experience! Alessandro was knowledgeable, friendly and very personable! The cities were so quaint and the Siena Cathedral was amazing!! I highly recommend the lunch at the winery; the highlight of our trip and beautiful surroundings. The food was delicious! This is a tour well worth the money! Don’t miss out! 5 Stars Plus!
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
- $390 to $680
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 94
- Verdict
- Exceptional
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 84
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Day Trip Siena, San Gimignano and Chianti from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Day Trip Siena, San Gimignano and Chianti from Florence cost?
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Prices start at $390 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 Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence worth it?
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It holds an Outty Ranking of 84 out of 100, which we label "Exceptional". That score blends traveler sentiment (5/5 across 269 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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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 Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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Around 94 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 Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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Included: English-speaking licensed driver; On-Board WiFi; Unlimited cold mineral water; Free time in Siena and San Gimignano; and Private transportation by MiniVan, Air-Conditioned. Always check the voucher for the final list before you travel.
Does Private Day Trip Siena, San Gimignano and Chianti from Florence include hotel pickup?
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Yes, pickup is offered for every traveler from 432 listed pickup locations in and around Florence. You can also enter a custom pickup address when booking.
What languages is Private Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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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 Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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Across 269 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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