Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in Ravenna, Italy
Ravenna, Italy

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Outty Ranking 88 4.9 · 442 traveler reviews8 hoursFrom $811
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Outty Ranking

88/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 442 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence worth booking?

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence is a 8-hour experience in Ravenna, Italy, from $811 per person. It scores 88 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.9/5 rating across 442 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
88 / 100
Rating
4.9/5 (442)
Duration
8 hours
From
$811 per person

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni (just if you won't need a stop for lunch) and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers.

What you get

    About this experience

    *Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni (just if you won't need a stop for lunch) and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers.

    What's included

    Included

    • expert english speaking driver
    • Bottled water
    • Onboard Wi-Fi (on request at reservation)
    • In-vehicle air conditioning
    • Private luxury car or minivan
    • Hotel pickup and drop-off in Florence

    Not included

    • Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult
    • mance
    • Licensed Guide in Siena

    What you'll see and do

    1. Siena

      Siena is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste or taste local food or buy some gifts!

      120 minutes here

    2. San Gimignano

      *Option to organize lunch at a Farm/Winery for home made lunch with wine tasting (to be payed on site). We have several options about wineries. (This option will reduce the time in the cities of Siena and/or San Gimignano and exclude Monteriggioni).

      120 minutes here

    3. Strada Statale 222 Chiantigiana

      We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!

      Pass by without stopping

    4. Historic Centre of San Gimignano

      Here we are in the beautiful stronghold of San Gimignano. Freeze at the age 1300dc, San Gimignano a pearl of medieval architecture famous for its houses tower! This is our last spot of the day before returning to Florence

      120 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.
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Chianti Drivers private tours

    Know before you go

    • Specialized infant seats are available
    • Infants and small children can ride in a pram or stroller
    • Suitable for all physical fitness levels
    • A maximum of seven people per booking

    Photos

    Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in Ravenna, photo 2Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in Ravenna, photo 3Siena drone pic!!!, Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in RavennaPrivate Tour in Siena, San Gimignano and Chianti Day Trip from Florence in Ravenna, photo 5Wine Tasting, Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in RavennaSangimignano, Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence in Ravenna

    What travelers are saying

    Outty’s summary of the themes that recur across 438 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    8 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    4 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    4 mentions

    The views and photo stops come up again and again.

    Food and drink

    4 mentions

    The tastings and food stops are a highlight for most reviewers.

    Traveler reviews

    438 verified traveler reviews for Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    404
    4 star
    13
    3 star
    13
    2 star
    5
    1 star
    3
    Sort
    Troy_Z · October 2026

    Ask for Cosimos

    We had the best experience today with Cosimos. It was one of the best days on any vacation I have been on. He speaks English beautifully and was so helpful with suggestions. We visited San Gimighano and experienced a family run vineyard and had a wonderful lunch and wine tasting and tour with lots of information and also met the owner. Then we visited Siena and toured the famous duomo de Siena and the surrounding village with shops, restaurants, etc. Such a beautiful experience. Theresa Z.

    via Viator

    JP3 · October 2026

    Amazing Honeymoon Tour

    Amazing tour with my wife and I to celebrate our honeymoon. Tour guide was super useful and took many pictures of us as we discovered the Tuscany region

    via Viator

    mickir260 · September 2026

    A Beautiful Day in Tuscany

    André was a wonderful driver…friendly, articulate, knowledgeable and engaging. We had expected him to accompany us at locations rather than just drop us off. The vehicle was first rate and comfortable even in the rear seat. We felt the price was too high for just transportation services. However, we did have a great day at all 3 stops and a lovely ride through the countryside.

    Response from the operator: Thank you very much dear!

    via Tripadvisor

    Kathryn_H · September 2026

    Awesome

    It was a wonderful experience, we had an incredible driver. Be aware that your driver stays with the vehicle while you explore the different places you visited. These places are very hilly so be prepared for that and have a raincoat or umbrella handy, just in case. Also you HAVE to add the wine and food tasting to your trip, it was one of our favorite parts. Thank you Sara for such a wonderful experience!

    Response from the operator: it's a pleasure and I will share to Sara as well

    via Viator

    Richa_S · August 2026

    Beautiful Tuscany - Great Tour

    Our tour guide Massimo was amazing. he knew all the right places, the right choices. the car was great, and he drove so well. we had a ton of fun.

    Response from the operator: thank you dear

    via Viator

    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
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    155
    Verdict
    Exceptional

    Who runs this experience

    Operated by Chianti Drivers private tours, who run 11 experiences we rank across 3 cities, with an average Outty Ranking of 52.7.

    See everything Chianti Drivers private tours runs

    Why this scores 88

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)92
    Review evidence (18% weight)100
    Booking momentum (14% weight)100
    Value for money (12% weight)49
    Listing quality (10% weight)85
    Local standing (8% weight)76
    Booking flexibility (8% weight)100

    Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Ravenna.

    How much does Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence cost?

    +

    Prices start at $811 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Ravenna usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Private Tour in Siena, San Gimignano and Chianti Day Trip 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 Ravenna is not rushed.

    Is Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence worth it?

    +

    It holds an Outty Ranking of 88 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 442 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most highly reviewed in Ravenna, and how flexible the cancellation terms are.

    Can I cancel or reschedule Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence?

    +

    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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence suitable for kids and families?

    +

    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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence?

    +

    Around 155 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 Ravenna 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 Ravenna and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.

    Where does Private Tour in Siena, San Gimignano and Chianti Day Trip 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 Ravenna 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 Ravenna?

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    On Outty we rank every Ravenna experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Guided Tour of Mosaic Tiles in Ravenna, Ravenna: Mosaics and Highlights Guided Tour with Admission Ticket, Ravenna Port to Venice with Deluxe Tour by Boat and Gondola. 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 Ravenna?

    +

    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 Ravenna?

    +

    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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence?

    +

    Included: expert english speaking driver; Bottled water; Onboard Wi-Fi (on request at reservation); In-vehicle air conditioning; and Private luxury car or minivan. Not included: Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult; mance; and Licensed Guide in Siena. Always check the voucher for the final list before you travel.

    Does Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence include hotel pickup?

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    Yes, pickup is offered for every traveler from 40 listed pickup locations in and around Ravenna. You can also enter a custom pickup address when booking.

    Will I get instant confirmation and a mobile ticket for Private Tour in Siena, San Gimignano and Chianti Day Trip 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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence wheelchair or stroller accessible?

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    The operator notes: Specialized infant seats are available; and Infants and small children can ride in a pram or stroller. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence if the weather is bad?

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    It generally runs rain or shine, so dress for the forecast in Ravenna. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence?

    +

    Across 442 reviews averaging 4.9 out of 5, recurring themes include the guide, knowledge and storytelling, photo opportunities. Travelers single out the guide as the reason the experience works.

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