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

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

Outty Ranking 58 4.8 · 23 traveler reviews8 hoursFrom $950

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September 2026

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Outty Ranking

58/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

4.8/5

Based on 23 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

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

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence is a 8-hour experience in Florence, Italy, from $950 per person. It scores 58 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 4.8/5 rating across 23 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
58 / 100
Rating
4.8/5 (23)
Duration
8 hours
From
$950 per person

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raise

What you get

    About this experience

    Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! If you love to visit the cathedral there will be to pay at the guide directly euro 5 per person or euro 7pp with priority -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano.

    What's included

    Included

    • Bottled water
    • Private Guide in the city of Siena
    • Onboard Wi-Fi (on request at reservation)
    • Hotel pickup and drop-off in Florence
    • Private Guide in the wine cellar

    Not included

    • Lunch
    • Gratuities
    • Museum/churches fee

    What you'll see and do

    1. Siena

      Followed by an authorized guide you will visit 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 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste local food or buy some gifts!

      120 minutes here

    2. Strada Statale 222 Chiantigiana

      enchanting country road surronded by greenery of vineyards and olive trees - stop for pictures/shooting

      60 minutes here

    3. *As OPTION* We can organize a Lunch in a Farm/winery with wine tasting. (to be paid on the spot) at Casa Emma or several other options This option will reduce the time in the cities of Siena and/or San Gimignano and will exclude Monteriggioni.

      120 minutes here · Admission not included

    4. San Gimignano

      A pearl of medieval architecture famous for its tower houses! Free time for the last stop in the incredible San Gimignano, a dive into the Middle Ages.

      60 minutes here

    5. Strada Statale 222 Chiantigiana

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

      Pass by without stopping

    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 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
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    • A maximum of 7 people per booking
    • Drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs.

    Photos

    S.Gimignano on the topPrivate Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence in Florence, photo 3Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence in Florence, photo 4Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence in Florence, photo 5Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence in Florence, photo 6Sangimignano

    What travelers are saying

    Outty’s summary of the themes that recur across 23 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    9 mentions

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

    Food and drink

    8 mentions

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

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Small groups

    2 mentions

    The group size is repeatedly described as intimate rather than packed.

    Traveler reviews

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

    5 star
    20
    4 star
    2
    3 star
    0
    2 star
    1
    1 star
    0
    Sort
    Wander15577008171 · June 2026

    Unforgettable trip!

    These towns can’t be missed. We had the pleasure of spending the day with Giacomo. His strong English skills allowed for great conversation. He is deeply knowledgeable about the history of Italy and Tuscany. He was kind enough to make a small detour to the American cemetery outside of Florence, and a small monastery near San Gimignano that were deeply moving. Lunch was at a beautiful winery, Terre Di Sovernaja, overlooking the Tuscan hills. The food was simple and so delicious, complimented perfectly with their wine. We explored San Gimignano on our own and Giacomo guided us through Siena with a stop for a quick espresso at an off the path cafe. His warmth and deep knowledge made for a memorable experience overall.

    Response from the operator: Dearest, so happy about your review. Your tour booked was with a driver and licensed guide in Siena so I reserved for you Giacomo as he is driver/guide. See you next time!!! all my best

    via Tripadvisor

    GeneAndDeanWeen · May 2025

    The only driver service I book as an expat in Italy for 2 decades!

    I have lived in Italy for nearly 20 years and whenever I have friends or family visiting, I book Massimo as our driver. Some of my most memorable experiences in Italy have been out on an excursion with Chianti Drivers! This April, Massimo picked us up in Florence and took us to San Gimignano and Monteriggioni for time to explore on our own. Next, we headed to an exquisite winery for lunch and a cellar tour, before heading to Siena. Massimo is always exceedingly professional, punctual and polite. I cannot recommend this company enough!

    Response from the operator: much appreciated, thanks

    via Tripadvisor

    Anne_M · March 2025

    Highly Recommend!

    Simone was wonderful. He was prompt, flexible and had a lot of interesting information to share. Our guide in Siena was very knowledgeable.

    Response from the operator: thank you dearest, hope we will see you soon!!

    via Viator

    Richard_H · May 2024

    I take the tour again

    Great info provided by Massimo along the way. Viviana gave a tour of Siena. Wine tasting at Emma’s winery was superb!

    Response from the operator: thank you

    via Viator

    yobisss · April 2024

    Excellent tour. 10 stars!!!

    We had an absolutely fantastic time. Two couples visiting from the United States. Simone, our driver, could not have been better. His knowledge was excellent. He took us on back roads and pointed out so many things we never would’ve gotten to see otherwise. The visit to Casa Emma Winery was above par and the food was excellent. The wine was quite tasty and the winery was absolutely beautiful. We highly recommend this company for a tour.

    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
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    8
    Verdict
    Worth a Look

    Why this scores 58

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

    Traveler sentiment (30% weight)82
    Review evidence (18% weight)42
    Booking momentum (14% weight)34
    Value for money (12% weight)0
    Listing quality (10% weight)85
    Local standing (8% weight)58
    Booking flexibility (8% weight)100

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

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

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

    +

    Prices start at $950 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 Tour: Siena, San Gimignano and Chianti Day Trip from Florence take?

    +

    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 Tour: Siena, San Gimignano and Chianti Day Trip from Florence worth it?

    +

    It holds an Outty Ranking of 58 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 23 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 Tour: 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 Guided Tour: 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 Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence?

    +

    Around 8 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?

    +

    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 Tour: Siena, San Gimignano and Chianti Day Trip from Florence start and how do I get there?

    +

    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?

    +

    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 Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. 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?

    +

    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?

    +

    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?

    +

    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.

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