Exclusive Siena and San Gimignano Tour & Chianti Wine Experience in Florence
Florence, Italy

Exclusive Siena and San Gimignano Tour & Chianti Wine Experience

Outty Ranking 70 4.7 · 33 traveler reviews10.5 hoursFrom $148

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September 2026

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Outty Ranking

70/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 33 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Exclusive Siena and San Gimignano Tour & Chianti Wine Experience worth booking?

Exclusive Siena and San Gimignano Tour & Chianti Wine Experience is a 10.5-hour experience in Florence, Italy, from $148 per person. It scores 70 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 4.7/5 rating across 33 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
70 / 100
Rating
4.7/5 (33)
Duration
10.5 hours
From
$148 per person

Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany. The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have

What you get

    About this experience

    Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany. The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral. No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany. End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture. A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!

    What travelers are saying

    Outty’s summary of the themes that recur across 30 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.

    Food and drink

    4 mentions

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

    Good for families

    3 mentions

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

    Small groups

    3 mentions

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

    Value for money

    2 mentions

    Travelers feel they got more than they paid for.

    Traveler reviews

    30 verified traveler reviews for Exclusive Siena and San Gimignano Tour & Chianti Wine Experience. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    25
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    Gill L · August 2026

    Poor value for money

    So I booked this tour to take the stress out of driving. I had a man in front of me almost in my lap due to a broken coach seat. We will look at it when we get back to base was not really good enough. As usual, when you go on these trips, there was not enough time spent in any of the areas we visited. We paid 195 Euros to be dragged around on a leash. The guide, although very nice, did just walk on up ahead with her flag, keep up, or get lost, basically. There were elderly people on our trip, and if any of them had fallen or taken ill, she would not have known. The day following this trip, we made our own way to Pisa and Lucca on the train. Much cheaper, I mean 140 Euros cheaper and a much more relaxed day.

    via Tripadvisor

    193gilll · August 2026

    Poor value for money

    I have mixed feelings. We booked direct through our hotel and it was easy. Location for picking up was straight forward. Once on the coach I had a man almost sitting on my lap the whole journey due to a broken coach seat, there was no option to move as the coach was full. When we stopped, other than Siena we did not get enough time in any of the locations. The time walking to and from meeting points was eating into our short time in each location. The guide, although very pleasant was just walking on ahead with her flag expecting everyone to keep up. We had a few older people on our trip and had they fallen or taken ill she would never have known. She walked to fast and at the back no one could hear her, which left confusion over some of the meeting times. Wine tasting was all about locking you in as their captive audience so they could sell you 60e bottles. Not for me an I won't book another coach tour. We thought we would just try something different this time. Do yourselves a favour hire a car and do the trips as day trips independently. It's cheaper and you can manage your own schedule. I felt like I was just driven to a stop , tipped into a shop or two, left to spend and then be picked up at the end.

    via Tripadvisor

    ayaz628 · June 2026

    Amazing Siena and Countryside Tour

    My family and I booked a private tour to visit the beautiful countryside and see towns like Siena and San Gimignano. Our tour guide Cristian, was so knowledgeable and he really helped us see the beauty of Italy and its different wonders. He was so easy and fun to talk to as we bonded over our culture and background. We were so grateful to have gotten him as our tour guide and we couldn’t have asked for a better one 💓💓

    via Tripadvisor

    toddbU2786OW · June 2026

    Wonderful experience

    Christian took excellent care of us, gave us great suggestions and treated us like family.

    via Tripadvisor

    Departure01850751297 · June 2026

    Fabulous Tour!

    Christian was a great guide and provided a lot of helpful information. He enhanced our first time in Italy both on the way to our destination and gave helpful recommendations for the rest of our trip.

    via Tripadvisor

    Good to know

    Duration
    10.5 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    12
    Verdict
    Strongly Recommended

    Why this scores 70

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

    Traveler sentiment (30% weight)78
    Review evidence (18% weight)47
    Booking momentum (14% weight)40
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)51
    Booking flexibility (8% weight)100

    Exclusive Siena and San Gimignano Tour & Chianti Wine Experience: questions travelers ask

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

    How much does Exclusive Siena and San Gimignano Tour & Chianti Wine Experience cost?

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    Prices start at $148 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 Exclusive Siena and San Gimignano Tour & Chianti Wine Experience take?

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    Plan for about 10.5 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 Exclusive Siena and San Gimignano Tour & Chianti Wine Experience worth it?

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    It holds an Outty Ranking of 70 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.7/5 across 33 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 Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?

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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 Exclusive Siena and San Gimignano Tour & Chianti Wine Experience suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 10.5-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?

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    Around 12 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 10.5-hour experience runs outdoors or after sunset.

    Where does Exclusive Siena and San Gimignano Tour & Chianti Wine Experience 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 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?

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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.

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