San Gimignano, Chianti, and Montalcino Day Trip from Siena
Siena, Italy

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Outty Ranking 71 4.3 · 156 traveler reviews11 hoursFrom $177
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Outty Ranking

71/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.3/5

Based on 156 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is San Gimignano, Chianti, and Montalcino Day Trip from Siena worth booking?

San Gimignano, Chianti, and Montalcino Day Trip from Siena is a 11-hour experience in Siena, Italy, from $177 per person. It scores 71 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.3/5 rating across 156 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
71 / 100
Rating
4.3/5 (156)
Duration
11 hours
From
$177 per person

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Montalcino, and savour local snacks, olive oil and balsamic vinegar – all in a comfortable small-group vehicle.Travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people. Note:Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited

What you get

    About this experience

    Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Montalcino, and savour local snacks, olive oil and balsamic vinegar – all in a comfortable small-group vehicle.Travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people. Note:Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited

    What's included

    Included

    • Expert multilingual escorts
    • Lunch
    • Olive oil and balsamic vinegar sampling
    • Alcoholic beverages
    • Meals
    • Tour of 2 wine estates, one of which is exclusive + 2 wine tastings

    Not included

    • Gratuities

    What you'll see and do

    1. San Gimignano 1300

      Free time in San Gimignano

      60 minutes here

    2. Collegiata di Santa Maria Assunta - Duomo di San Gimignano

      During your free time opt to visit the Cathedral of San Gimignano

      15 minutes here · Admission not included

    3. Piazza Della Cisterna

      Free time in San Gimignano

      15 minutes here

    4. Palazzo Pubblico e Torre Grossa

      Free time in San Gimignano

      15 minutes here · Admission not included

    5. Strada Statale 222 Chiantigiana

      Lunch and wine tasting in a local winery in Montalcino

      60 minutes here · Admission included

    6. Fortezza di Montalcino

      Free time in Montalcino

      60 minutes here

    7. San Filippo Montalcino

      Free time in Montalcino

      Pass by without stopping

    8. Siena

      Start your trip at Siena Station Ferrovia, where you will meet the staff. You will recognize them by their green shirt. You will travel by minivan.

      40 minutes here

    Where it starts and ends

    Meeting point

    Siena

    Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en, it, es
    Ticket
    Mobile Only
    Runs on
    Mon, Thu, Sun
    Group size
    Up to 8 travelers per booking
    Operated by
    myTour in 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
    • Customers must be able to climb and descend stairs.
    • Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking
    • Travel in air-conditioned minivan for up to 8 people or minibus for up to 30 people
    • Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.

    Photos

    San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 2San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 3San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 4San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 5San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 6San Gimignano, Chianti, and Montalcino Day Trip from Siena, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 156 traveler reviews. Written by us, not quoted from reviewers.

    Food and drink

    7 mentions

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

    The guide

    5 mentions

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

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Small groups

    2 mentions

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

    Traveler reviews

    156 verified traveler reviews for San Gimignano, Chianti, and Montalcino Day Trip from Siena. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    104
    4 star
    25
    3 star
    8
    2 star
    7
    1 star
    12
    Sort
    Joni_F · October 2026

    Tour was canceled 2 days before the tour date.

    Our tour was canceled 2 days before the tour date by the vendor. I am so disappointed that I did not get to go to San Gimignano!!! It was replaced with a trip that we were told would be similar. We were very unhappy with the replacement tour. It was a large bus full of people, not a small group tour that we were looking forward too. The guide had to interpret everything into English, Spanish and Italian. While I am amazed at her skill, I believe we received less historical information because everything had to be translated into 3 languages. We signed up for this tour months in advance and now we didn’t get to see San Gimignano. We are very disappointed.

    via Viator

    dpdipalma · October 2026

    This tour was cancelled 48 hrs before it was to begin.

    The company will cancel with very short notice and without giving a reason. (“Technical difficulties”). So don’t count on them for your trip planning. I presume that the true reason for the cancellation was because there weren’t enough people signed up to make it a full tour group. Still very disappointing to have so little notice and have to come up with a replacement itinerary. My credit card was charged none the less, as they presumed we would accept an offered alternative tour, which we did not want. After a day and a few emails, the charge was reversed. The experience has left a bad impression of Viator for me.

    Response from the operator: Dear Customer, Thank you for sharing your feedback with us. We would like to clarify that when we offer an alternative tour, the decision to accept or decline it is entirely yours. If you choose not to accept the alternative, we proceed with the refund accordingly. We always strive to handle these situations professionally and ensure that our customers are treated fairly. We sincerely apologize for any inconvenience caused and appreciate your understanding. Kind regards, my Tour

    via Viator

    Zenaida_C · September 2026

    Wonderful , exceptional...

    Wonderful , exceptional experience in Tuscany’s world renowned wine towns. Immersive and comprehensive.

    Response from the operator: Dear Customer, Thank you for your feedback! We’re delighted to hear you had an exceptional experience discovering Tuscany and its renowned wine towns. We hope to welcome you again soon! Best regards, my Tour in Italy

    via Viator

    Navigate52558492644 · September 2026

    Absolutely surreal

    The experience was great. We had the chance to visit multiple towns out in the countryside of Italy near Sienna/Tuscany. Offered exquisite glasses of wine, a lunch, and visited iconic landmarks along the way. Huge shout-out to our tour guide Bianca for making the journey fantastic and an unforgettable experience.

    Response from the operator: Dear Customer, We’re delighted to hear you enjoyed exploring the Tuscan countryside, the wine, lunch, and iconic landmarks. A special thank you for your kind words about Bianca; we’ll be sure to share them with her! Best regards, my Tour

    via Tripadvisor

    Mei_X · May 2026

    Nicely organized tour,...

    Nicely organized tour, great food and wine. San Gimignano is beautiful but packed with tourists (including myself too) during mid day. Would love to visit it during some quieter time if any.

    Response from the operator: Dear Customer, Thank you for your feedback! We're delighted that you enjoyed the tour, the food, and the wine. We appreciate your comment about San Gimignano and hope you'll have the chance to experience its quieter side in the future. Kind regards, my Tour in Italy

    via Viator

    Good to know

    Duration
    11 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Thu, Sun
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    55
    Verdict
    Strongly Recommended

    Who runs this experience

    Operated by myTour in Italy, who run 51 experiences we rank across 5 cities, with an average Outty Ranking of 57.8.

    See everything myTour in Italy runs

    Why this scores 71

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

    Traveler sentiment (30% weight)54
    Review evidence (18% weight)86
    Booking momentum (14% weight)83
    Value for money (12% weight)100
    Listing quality (10% weight)82
    Local standing (8% weight)0
    Booking flexibility (8% weight)100

    San Gimignano, Chianti, and Montalcino Day Trip from Siena: questions travelers ask

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

    How much does San Gimignano, Chianti, and Montalcino Day Trip from Siena cost?

    +

    Prices start at $177 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does San Gimignano, Chianti, and Montalcino Day Trip from Siena take?

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    Plan for about 11 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 Siena is not rushed.

    Is San Gimignano, Chianti, and Montalcino Day Trip from Siena worth it?

    +

    It holds an Outty Ranking of 71 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.3/5 across 156 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.

    Can I cancel or reschedule San Gimignano, Chianti, and Montalcino Day Trip from Siena?

    +

    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 San Gimignano, Chianti, and Montalcino Day Trip from Siena suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 11-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book San Gimignano, Chianti, and Montalcino Day Trip from Siena?

    +

    Around 55 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 Siena 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 Siena and add a light layer if any part of the 11-hour experience runs outdoors or after sunset.

    Where does San Gimignano, Chianti, and Montalcino Day Trip from Siena 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 Siena 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 Siena?

    +

    On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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 Siena?

    +

    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 Siena?

    +

    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.

    What is included in San Gimignano, Chianti, and Montalcino Day Trip from Siena?

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    Included: Expert multilingual escorts; Lunch; Olive oil and balsamic vinegar sampling; Alcoholic beverages; and Meals. Not included: Gratuities. Always check the voucher for the final list before you travel.

    Where is the meeting point for San Gimignano, Chianti, and Montalcino Day Trip from Siena?

    +

    Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is San Gimignano, Chianti, and Montalcino Day Trip from Siena offered in?

    +

    It is offered in English, Italian and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for San Gimignano, Chianti, and Montalcino Day Trip from Siena?

    +

    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is San Gimignano, Chianti, and Montalcino Day Trip from Siena wheelchair or stroller accessible?

    +

    The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to San Gimignano, Chianti, and Montalcino Day Trip from Siena if the weather is bad?

    +

    It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about San Gimignano, Chianti, and Montalcino Day Trip from Siena?

    +

    Across 156 reviews averaging 4.3 out of 5, recurring themes include food and drink, the guide, photo opportunities. The tastings and food stops are a highlight for most reviewers.

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