Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence
Florence, Italy

Florence: Siena & San Gimignano with Dinner in a Boutique Winery

Outty Ranking 80 4.7 · 311 traveler reviews9 hoursFrom $107

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September 2026

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Outty Ranking

80/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 311 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Florence: Siena & San Gimignano with Dinner in a Boutique Winery worth booking?

Florence: Siena & San Gimignano with Dinner in a Boutique Winery is a 9-hour experience in Florence, Italy, from $107 per person. It scores 80 out of 100 on the Outty Ranking, which we label “Exceptional, based on a 4.7/5 rating across 311 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
80 / 100
Rating
4.7/5 (311)
Duration
9 hours
From
$107 per person

Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo,

What you get

    About this experience

    Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location. Looking for the full Tuscan experience? Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.

    What's included

    Included

    • Free WiFi on board
    • English speaking driver/tour leader
    • Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option
    • Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan
    • Guided walking tour of Siena
    • Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included)
    • Visit of a winery with wine tasting
    • Surprise tasting in Siena
    • San Gimignano visit with free time
    • Free Time in San Gimignano

    Not included

    • Gratuities
    • Hotel pickup and drop-off
    • We are sorry to inform you that pets are not permitted on our tours
    • Tuscany Grand Tour Option: Entrance ticket to the Tower of Pisa (purchase on-site if time allows)

    What you'll see and do

    1. Florence

      Towns of Italy indicated meeting point

      Pass by without stopping

    2. Siena

      Arrival in Siena for a guided tour

      120 minutes here

    3. Historic Centre of San Gimignano

      Free time in San Gimignano, UNESCO Heritage Site

      60 minutes here

    4. Diadema Wine & Evo

      Gourmet Dinner in a Boutique Winery in Chianti

      60 minutes here · Admission included

    5. Florence

      Return to Florence and end of the tour at the initial meeting point

      Pass by without stopping

    Where it starts and ends

    Meeting point

    Florence

    Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)

    Options you can book

    • Small Group: Siena & Dinner

      Afternoon with dinner: Siena & San Gimignano in a premium small group (max 20) by Mercedes minivan—top-tier tour with winery dinner included!

    • Essential Coach Tour & Dinner

      Afternoon with Dinner : Siena & San Gimignano by coach - top Tuscan sights and a typical dinner at a winery—great experience, budget-friendly price!

    • Private Siena and San Gimignano tour with dinner

      Private Group: Siena & Dinner: Private Afternoon in Siena & San Gimignano with Traditional Winery Dinner

    • Semiprivate Tuscany Grand Tour

      Upgrade to the Grand Tour:: Full-day (12h) with 8 AM departure: Siena, San Gimignano, Chianti, Pisa & Tuscan lunch—semiprivate journey (max 8) in style!

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Towns of Italy

    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
    • The tour operates regardless of weather conditions
    • Semiprivate Tuscany Grand Tour Option: Choose the Grand Tour upgrade for a full-day experience starting at 8:00 AM. Discover the highlights of Tuscany in one unforgettable journey: visit Siena with a guided walking tour and a surprise tasting, enjoy free time in the medieval town of San Gimignano, savor a traditional Tuscan lunch, then continue to Pisa to admire the stunning Piazza dei Miracoli and the iconic Leaning Tower (tower tickets not included). The experience includes round-trip transportation from Florence in a luxury Mercedes minivan with free Wi-Fi, an English-speaking driver/tour leader, and all the charm, history, and flavor of Tuscany in one complete itinerary.

    Photos

    Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 2Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 3Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 4Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 5Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 6Florence: Siena & San Gimignano with Dinner in a Boutique Winery in Florence, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 311 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

    7 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

    4 mentions

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

    Traveler reviews

    311 verified traveler reviews for Florence: Siena & San Gimignano with Dinner in a Boutique Winery. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    256
    4 star
    31
    3 star
    12
    2 star
    8
    1 star
    4
    Sort
    P9806MLjulier · August 2026

    Fun evening in Siena, San Gimignano, and at a boutique winery.

    Wonderful day trip away from the hustle and bustle of Florence. Our driver, Christina, was friendly, efficient, and knowledgeable. We had a wonderful time!

    via Tripadvisor

    lauraaX2789KZ · August 2026

    Tuscany Wine Tour

    Francesco was amazing! He was entertaining, kind, and an all around blast to have as a driver! He enlightened us with history and showed us beautiful sights along our way to Siena and a wine tour in Chantai! Highly recommend!

    via Tripadvisor

    V3642AWnatashad · August 2026

    A wonderful introduction to Tuscany

    This was an excellent change from the usual tours in Florence, and a great introduction to the other must-see towns of Tuscany. The group was sized perfectly and felt intimate. Our guide at Siena was excellent and managed to cram in a lot of sights in a short time. We had plenty of time to get a taste of San Gimigiano, and the dinner at the winery felt homely - like having a meal at a friend’s home. Most of all, our driver/guide was very accommodating and helpful to my family, who genuinely appreciated her hospitality. I highly recommend this tour if you’re looking for a wider taste of Tuscany!

    via Tripadvisor

    jameskD8990LE · August 2026

    Fun times on Tuscany Tour with Family

    Tour guides on the school leg were very nice and helpful. Cities were both fascinating places - distinctly ancient but very different. Winery was excellent and authentic experience, and the owner and staff were very knowledgeable and hospitable. Some minor feedback: In Siena, it would be great to allow for time to visit the Duomo. But overall an excellent experience.

    via Tripadvisor

    mldm23 · August 2026

    Siena and San Gimignano Tour with Federico

    Our tour with Federico was wonderful and authentic. We will have memories forever of the excellent service and thorough explanations of amazing locations including San Gimignano, Siena, Fattoria Di Bagnolo. Federico was incredible and so informative. I highly recommend!

    via Tripadvisor

    Good to know

    Duration
    9 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $107 to $615
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    109
    Verdict
    Exceptional

    Why this scores 80

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

    Traveler sentiment (30% weight)79
    Review evidence (18% weight)77
    Booking momentum (14% weight)73
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)52
    Booking flexibility (8% weight)100

    Florence: Siena & San Gimignano with Dinner in a Boutique Winery: questions travelers ask

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

    How much does Florence: Siena & San Gimignano with Dinner in a Boutique Winery cost?

    +

    Prices start at $107 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 Florence: Siena & San Gimignano with Dinner in a Boutique Winery take?

    +

    Plan for about 9 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 Florence: Siena & San Gimignano with Dinner in a Boutique Winery worth it?

    +

    It holds an Outty Ranking of 80 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.7/5 across 311 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 Florence: Siena & San Gimignano with Dinner in a Boutique Winery?

    +

    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 Florence: Siena & San Gimignano with Dinner in a Boutique Winery suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Florence: Siena & San Gimignano with Dinner in a Boutique Winery?

    +

    Around 109 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 9-hour experience runs outdoors or after sunset.

    Where does Florence: Siena & San Gimignano with Dinner in a Boutique Winery 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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