Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region in Florence
Florence, Italy

Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

Outty Ranking 76 4.7 · 151 traveler reviews8 hoursFrom $105

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September 2026

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From, per person$105
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Outty Ranking

76/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 151 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region worth booking?

Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region is a 8-hour experience in Florence, Italy, from $105 per person. It scores 76 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 4.7/5 rating across 151 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
76 / 100
Rating
4.7/5 (151)
Duration
8 hours
From
$105 per person

Enjoy a day away from Florence as you visit Siena, San Gimignano and the picture-postcard Chianti area. Take your time to appreciate everything Tuscany has to offer. Enjoy the personalized attention of your private drive

What you get

    About this experience

    Enjoy a day away from Florence as you visit Siena, San Gimignano and the picture-postcard Chianti area. Take your time to appreciate everything Tuscany has to offer. Enjoy the personalized attention of your private driver and breath in the Medieval atmosphere surrounding Siena and San Gimignano, two authentic jewels nestled in the heart of Tuscany. On the way back to your hotel in Florence, enjoy breathtaking views of the gentle hills and vineyards of the Chianti wine region. Hotel pickup and drop-off and a driver is included.

    What travelers are saying

    Outty’s summary of the themes that recur across 151 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    7 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.

    Photo opportunities

    3 mentions

    The views and photo stops come up again and again.

    Small groups

    3 mentions

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

    Traveler reviews

    151 verified traveler reviews for Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    135
    4 star
    4
    3 star
    5
    2 star
    2
    1 star
    5
    Sort
    N8233NBerica · July 2026

    ⭐️⭐️⭐️⭐️ A Truly Outstanding Guide — Cristian Made Our Day Unforgettable

    ⭐️⭐️⭐️⭐️⭐️ A Truly Outstanding Guide — Cristian Made Our Day Unforgettable During our stay in Florence, we had the absolute privilege of spending a full 10 hours with Cristian as our private tour guide, and I can say without hesitation that he is one of the best guides I have ever had—if not the best. Cristian took us from Florence to Pisa, through the Tuscan countryside, and into Siena and San Gimignano, delivering an experience that was nothing short of extraordinary. His professionalism stood out from the very beginning, but what truly elevated the day was his deep knowledge, warm personality, and unmatched level of care. Every stop came alive through his insight. Every question was answered with expertise. Every request—big or small—was met with genuine accommodation and enthusiasm. I’ve been on many tours around the world, and Cristian ranks at the very top. He is friendly, engaging, and incredibly thoughtful, striking the perfect balance between guiding, educating, and giving us space to enjoy each moment. His passion for Tuscany and its history shines through in everything he does. To Cristian’s supervisor: you have an exceptional asset on your team. To future travelers: if you have the chance to tour with Cristian, take it—you will be grateful you did. Cristian, thank you for an unforgettable day. Your dedication and kindness made our time in Italy truly special.

    via Tripadvisor

    Linda_B · July 2026

    Touring Tuscany

    Drive was exceptional to the locations. Views were picture perfect. Given enough freedom to explore. Lunch was amazing.

    via Viator

    X243WAjamesf · July 2026

    Great Day out in Tuscany on custom tour.

    Booked a custom private Tour which included additional locations versus standard private tour. Alessia gave very quick responses to get the tour priced and booked. Had a great day with our driver Diego and we hit all our timings and objectives for the visit. Highly recommended.

    via Tripadvisor

    Edlira Q · June 2026

    Amazing

    We enjoyed too much and we highly recommend this trip to everyone. We saw a lot of beautiful places and countrysides, the winery visit to chianti region was perfect. We tasted a lot of wine and they were all great.

    via Tripadvisor

    Susanne_M · June 2026

    It was a great day for...

    It was a great day for the 8 of us in our group. Our driver arranged lunch at a small winery where the owner gave us a tasting of his wines with lunch so we ended up with an extra wine tasting, a nice surprise.

    via Viator

    Good to know

    Duration
    8 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    53
    Verdict
    Strongly Recommended

    Why this scores 76

    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)67
    Booking momentum (14% weight)62
    Value for money (12% weight)100
    Listing quality (10% weight)75
    Local standing (8% weight)51
    Booking flexibility (8% weight)100

    Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region: questions travelers ask

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

    How much does Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region cost?

    +

    Prices start at $105 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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region 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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region worth it?

    +

    It holds an Outty Ranking of 76 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.7/5 across 151 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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?

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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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region 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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region?

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    Around 53 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 Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region 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?

    +

    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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