Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch in Florence
Florence, Italy

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Outty Ranking 93 4.9 · 1,811 traveler reviews10 hoursFrom $9990+ Club

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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Outty Ranking

93/100

90+ Club. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 1,811 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch worth booking?

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch is a 10-hour experience in Florence, Italy, from $99 per person. It scores 93 out of 100 on the Outty Ranking, which we label “90+ Club, based on a 4.9/5 rating across 1,811 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing. It sits in the Outty 90+ Club, the top tier of everything we rank.

Outty Ranking
93 / 100
Rating
4.9/5 (1,811)
Duration
10 hours
From
$99 per person

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. De

What you get

    About this experience

    Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. Depart from Florence, see the highlights of Siena through the eyes of a licensed guide, admire the marvelous Tuscan landscape, taste genuine Tuscan food paired with great wines, and finish your day relaxing in the hill top village of San Gimignano.

    What's included

    Included

    • Free time in San Gimignano
    • Small group day trip to Siena and San Gimignano from Florence
    • Lunch at a Tuscan winery, paired with their excellent red wines
    • Roundtrip transportation by air-conditioned minibus or minivan (Mercedes or similar) with free wi-fi
    • Optional: Entrance fee + tour of Siena Cathedral € 15pp payable to the guide Not available on Sun
    • Professional and informative English speaking guide + driver
    • Guided walking tour of Siena highlights + free time in Siena

    Not included

    • Hotel pickup and drop-off
    • Gratuities

    What you'll see and do

    1. Piazza del Campo

      Piazza del Campo

      60 minutes here

    2. Duomo di Siena

      Siena Cathedral

      60 minutes here

    3. Walls of Monteriggioni

      Monteriggioni

      Pass by without stopping

    4. Visit the estate, have a look at the old wine cellars. Take a seat and relax while enjoying a light lunch of seasonal Tuscan delicacies paired with a selection of great wines.

      90 minutes here · Admission included

    5. Historic Centre of San Gimignano

      Explore the medieval hill town of San Gimignano. Famous for its splendid skyline of tall medieval towers, have free time to explore on your own. Discover the main street full of typical shops, have a look at the Collegiata (main church), or enjoy a gelato.

      75 minutes here

    Where it starts and ends

    Meeting point

    Florence

    WHEN: 7:45am (at the latest) WHERE: on the left side of the street, opposite to the parking lot HOW: Look/ask for the PRESTIGE RENT staff, close to a red flag and the checkin table

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    WHEN: 7:45am (at the latest) WHERE: on the left side of the street, opposite to the parking lot HOW: Look/ask for the PRESTIGE RENT staff, close to a red flag and the checkin table

    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
    Prestige Rent

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    • Vegetarian & gluteen free, can be accommodated, please advise at time of booking under special requirements.
    • Siena Cathedral is not accessible on Sundays and during celebrations
    • Luggage can be stored on the bus during the tour, if needed
    • Return at departure point: approx. 6:00pm. To reserve other activities, allow plenty of time, in case of heavy traffic, etc.
    • Entrance fees + guided visit inside the Siena Cathedral, can be purchased directly from your guide, on the day of the tour - Euro 15,00 per person. Not available on Sundays or during celebrations
    • For cruise ship passengers only: if your ship docks at Livorno or La Spezia Port, be advised that the driving time to the meeting point in Florence is approx. 2 hours. Before booking, be sure your ship schedule works with our departure times, and you have your own transportation arranged from the port to Florence and back.
    • This is a shared tour and you will be expected to maintain the pace of the group. If you have limited mobility we highly recommend to book a private tour for your best enjoyment.

    Photos

    Guide in Siena - Palio di Siena 1Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch in Florence, photo 3Cured ham, salami and cheeseGuided TourGuide in Siena 1Guide in Siena

    What travelers are saying

    Outty’s summary of the themes that recur across 1,811 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

    6 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    5 mentions

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

    Small groups

    2 mentions

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

    Traveler reviews

    1,811 verified traveler reviews for Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    1,710
    4 star
    76
    3 star
    17
    2 star
    4
    1 star
    4
    Sort
    suegW7633LA · August 2026

    Unforgettable Tuscan Experience

    Acessic was fantastic an unforgettable Tuscan Tour deep with local knowledge and warmth

    via Tripadvisor

    Sunshine02721487725 · August 2026

    Incredible Experience

    Alessio was AMAZING and we had an incredible experience. The van was spacious and clean. We learned a lot about the region as we were driving. The tour in Siena from a local guide (Carlo) was absolutely fantastic. The winery & lunch was unbelievable and the perfect mix of informative but also enjoyment. Exploration time in San Gimignano was perfect. We would highly recommend this tour to anybody!

    via Tripadvisor

    sharip801 · August 2026

    Amazing day trip

    Alessio was amazing. Very knowledgeable and made us feel very comfortable during the entire trip!

    via Tripadvisor

    corrinnef2013 · August 2026

    Tuscany small group tour and wine tour

    Leo our driver was excellent. He has so much knowledge of the areas.

    via Tripadvisor

    Sergiy_K · August 2026

    We want to say a big...

    We want to say a big thank you to our wonderful guides, Leo and Sylvia from Siena, for such an interesting and enjoyable tour. We learned so much about the history of Siena. Leo was very welcoming and friendly. Our group was small, which made it feel almost like a private tour. The bus was also very comfortable. Thank you, Leo and Sylvia, for a wonderful experience! We highly recommend this

    via Viator

    Good to know

    Duration
    10 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $99 to $149
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    634
    Verdict
    90+ Club

    Why this scores 93

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

    Traveler sentiment (30% weight)93
    Review evidence (18% weight)100
    Booking momentum (14% weight)100
    Value for money (12% weight)100
    Listing quality (10% weight)72
    Local standing (8% weight)76
    Booking flexibility (8% weight)100

    Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch: questions travelers ask

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

    How much does Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch cost?

    +

    Prices start at $99 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 Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch take?

    +

    Plan for about 10 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 Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch worth it?

    +

    It holds an Outty Ranking of 93 out of 100, which we label "90+ Club". That score blends traveler sentiment (4.9/5 across 1,811 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Florence, and how flexible the cancellation terms are. Scoring 90 or above puts it in the Outty 90+ Club, the top tier of everything we rank.

    Can I cancel or reschedule Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch?

    +

    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 Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch?

    +

    Around 634 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 10-hour experience runs outdoors or after sunset.

    Where does Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch 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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