San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Siena, Italy

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Outty Ranking 79 4.5 · 201 traveler reviews11 hoursFrom $90
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Outty Ranking

79/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.5/5

Based on 201 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting worth booking?

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting is a 11-hour experience in Siena, Italy, from $90 per person. It scores 79 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.5/5 rating across 201 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
79 / 100
Rating
4.5/5 (201)
Duration
11 hours
From
$90 per person

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

What you get

    About this experience

    Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

    What's included

    Included

    • Caf Tour staff assistance at the meeting point for smooth check-in
    • Licensed English-speaking tour escort throughout the day
    • Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tuscan lunch
    • Departure from Florence
    • Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & vin santo
    • Round-trip transport by air-conditioned coach

    Not included

    • Guided Service in Siena
    • Cathedral admission in Siena
    • Hotel Pick-Up and Drop-Off is not available

    What you'll see and do

    1. Historic Centre of San Gimignano

      Explore a perfectly preserved walled hilltown famed for its soaring medieval towers and fresco-filled churches. Stroll the UNESCO-listed historic center at your own pace, browsing artisan shops and quiet lanes. Enjoy panoramic viewpoints over the Val d’Elsa and time for gelato or souvenirs.

      120 minutes here

    2. Monteriggioni

      Step inside a storybook fortress village encircled by intact 13th-century walls. Wander the tiny piazza and gates, soaking up its authentic medieval atmosphere. Quick, easy visit with great photo spots from the ramparts. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

      40 minutes here

    3. Strada Statale 222 Chiantigiana

      Cruise one of Tuscany’s most scenic roads, rolling past vineyards, olive groves, and stone farmhouses. Settle into a cozy winery for a guided tasting of three Chianti wines paired with a zero-mile, three-course lunch. Finish sweetly with traditional cantucci and vin santo.

      90 minutes here

    4. Siena

      Enjoy generous free time to feel Siena’s Gothic soul—narrow lanes, noble palaces, and lively enotecas. Browse artisan boutiques, sample local specialties, and capture the city’s warm, terracotta hues. Ideal for independent discovery and relaxed photos.

      120 minutes here

    5. Duomo di Siena

      Pause for an exterior and brief interior look at Siena’s striking striped-marble cathedral. Admire its ornate façade, sculptures, and masterworks that hint at the city’s artistic power. A swift but unforgettable highlight.

      15 minutes here · Admission not included

    6. Piazza del Campo

      Descend into one of Italy’s most beautiful squares, famed for the Palio horse race. Take a moment to sit at a café, admire the shell-shaped slope, and view the Torre del Mangia and Palazzo Pubblico. A perfect finale for people-watching and photos.

      30 minutes here

    Where it starts and ends

    Meeting point

    Siena

    An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

    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 8 travelers per booking
    Operated by
    CAF Tour and Travel - Gray Line Florence

    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
    • Travelers should have at least a moderate level of physical fitness
    • For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
    • Comfortable walking shoes are recommended
    • Please note that the order of the visits may change
    • It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the excursion, nor to have a refund or reschedule the tour.
    • Please be advised that it is required to bring your original ID with you during the tour
    • Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
    • Vegetarian and gluten-intolerant options are available at the wineries; however, cross- contamination cannot be fully excluded.

    Photos

    San Gimignano, San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine TastingSan Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting, photo 3San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting, photo 4Lunch with Wine Tasting, San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine TastingSan Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting, photo 6San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 198 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    7 mentions

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

    Organization

    3 mentions

    Pickup, timing, and logistics are described as running smoothly.

    Food and drink

    3 mentions

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

    Knowledge and storytelling

    2 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Traveler reviews

    198 verified traveler reviews for San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    138
    4 star
    38
    3 star
    14
    2 star
    7
    1 star
    1
    Sort
    Paula_G · October 2026

    Great value tour …highly recommended.

    A great day seeing the medieval cities .. and a delicious lunch at the winery with plenty of wine to taste and enjoy. Well organised and plenty of time at each place. More walking than I envisaged, as buses have to park outside the city centres, so be prepared for this. Our guides Ricky and Christina were great…and very helpful to me when I had to take it a little slower due to a recent injury during my travels. Great value for money.

    via Viator

    deanr204 · October 2026

    Beautiful and Interesting

    We had notice a day before one of the stops was cancelled due to a festival. Meeting our group at the bus was easy enough. We were informed how our day would go and we set off to our destinations. The stops seemed a little long on free time and the day was long. Our guide Michael, and the others did well to keep our group together and on time. The stops were beautiful and interesting.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Dean, Thank you for taking the time to share your feedback with us. We are pleased to hear that you found the stops beautiful and interesting and that the organization of the day was clear from the beginning. We are sorry that the day felt a little long and that you found some of the free-time periods longer than expected. We truly appreciate this feedback, as it helps us evaluate the pacing of our itineraries. We are also glad that Michael and the rest of the team were able to keep everyone together and on schedule throughout the tour. We hope that the beauty of San Gimignano, Siena, and the Tuscan countryside made the long day worthwhile, and we would be delighted to welcome you back to Tuscany in the future. Warm regards, Caf Tour & Travel Team

    via Tripadvisor

    David_R · September 2026

    We had an amazing day...

    We had an amazing day with Lily touring multiple different places throughout Tuscany. I can’t say enough about how great Lily was to work with and how fun she made the day. I would highly recommend this Danny one that’s considering it.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear David, Thank you so much for your fantastic review! We are thrilled to hear that you had such an amazing day exploring Tuscany with Lily. It is wonderful to know that Lily made the experience so much fun and that her company helped turn your day visiting the different Tuscan destinations into such a memorable adventure. We will be delighted to share your kind words with her! Thank you for recommending the tour, and we hope to welcome you back to Tuscany again soon. Warmly, Caf Tour & Travel Team

    via Viator

    Alan_M · September 2026

    Big day out

    Lily was a great guide. Amazing day well managed and plenty of free time in each location. It is a big day so pace yourself

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Alan, Thank you so much for your wonderful feedback! We are delighted that Lily helped make such a big day feel well managed and enjoyable, while still giving you plenty of free time to experience each destination at your own pace. With San Gimignano, Siena, Monteriggioni, lunch, and wine tasting all on the itinerary, it is certainly a full Tuscan adventure, and your advice to pace yourself is a good one! We hope you returned to Florence with wonderful memories of Tuscany and its timeless landscapes. Buon viaggio e alla prossima! Caf Tour & Travel Team

    via Viator

    Kasturi_C · September 2026

    Affordable tour. No luxuries but great guides and sights

    It’s lovely. But it’s a packed bus. The sights and the medieval towns were lovely. The lunch at the winery was lovely but the tour of the winery is basic.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Kasturi, Thank you very much for sharing your feedback! We’re pleased to hear that you enjoyed the beautiful medieval towns, the lunch at the winery and, above all, the guidance and hospitality of our team. This experience brings together several of Tuscany’s most iconic sights in one day, so the itinerary is intentionally quite full. We’re glad that you found the tour an enjoyable and accessible way to discover so much of the region. We also appreciate your comment regarding the winery visit. The focus of the experience is primarily on discovering the local wine tradition through the tasting and the setting, but we understand that some guests may enjoy a more in-depth cellar visit. Thank you again for joining us, and we hope to welcome you back to Tuscany in the future! Warm regards and a presto, Caf Tour & Travel

    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
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    70
    Verdict
    Strongly Recommended

    Who runs this experience

    Operated by CAF Tour and Travel - Gray Line Florence, who run 47 experiences we rank across 6 cities, with an average Outty Ranking of 55.4 and 1 in the 90+ Club.

    See everything CAF Tour and Travel - Gray Line Florence runs

    Why this scores 79

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

    Traveler sentiment (30% weight)66
    Review evidence (18% weight)90
    Booking momentum (14% weight)88
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)22
    Booking flexibility (8% weight)100

    San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting: questions travelers ask

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

    How much does San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting cost?

    +

    Prices start at $90 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting take?

    +

    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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting worth it?

    +

    It holds an Outty Ranking of 79 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.5/5 across 201 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.

    Can I cancel or reschedule San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    Around 70 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    Included: Caf Tour staff assistance at the meeting point for smooth check-in; Licensed English-speaking tour escort throughout the day; Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tu; Departure from Florence; and Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & vin s. Not included: Guided Service in Siena; Cathedral admission in Siena; and Hotel Pick-Up and Drop-Off is not available. Always check the voucher for the final list before you travel.

    Where is the meeting point for San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting offered in?

    +

    It runs in English. 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?

    +

    Across 201 reviews averaging 4.5 out of 5, recurring themes include the guide, organization, food and drink. Travelers single out the guide as the reason the experience works.

    Ready to lock in your spot?

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