San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.5/5
Based on 182 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 Florence, Italy, from $40 per person. It scores 72 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.5/5 rating across 182 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 72 / 100
- Rating
- 4.5/5 (182)
- Duration
- 11 hours
- From
- $40 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 Gi
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
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
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
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
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
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
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
Florence
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
What travelers are saying
Outty’s summary of the themes that recur across 182 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Pace and timing
2 mentionsSeveral reviewers comment on how the schedule is paced.
Traveler reviews
182 verified traveler reviews for San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting. Ratings and reviews provided by Viator and Tripadvisor.
#TuscanyLife
I really enjoyed this trip and it was a nice break from being in the city. It's a typical bus tour where everyone piles on from one stop to the next, but it gives you a great opportunity to visit some interesting sites. All the stops were great, including lunch at a vineyard with wine tasting. However, Siena was probably our favorite stop. Beautiful city and full of energy as the city prepared for the upcoming Palio di Siena horse race.
Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for sharing your #TuscanyLife experience! We’re delighted that the day offered you a refreshing break from the city and the chance to discover Siena and the beautiful medieval towns of Tuscany. It sounds like Siena truly stole the show, especially with the city buzzing ahead of the famous Palio di Siena! We’re also happy you enjoyed the vineyard lunch and wine tasting, and hope to welcome you back for another taste of the Tuscan lifestyle. Warmest wishes from Tuscany, Caf Tour & Travel
via Viator
Day trip in Tuscany
This was such a fun day trip through the Tuscan region, with wine tasting, a delicious lunch, and plenty of beautiful scenery along the way. The highlight for me was definitely spending the afternoon exploring Siena. A great way to experience the best of Tuscany in one day!
Response from the operator: Good Morning from Caf Tour & Travel, Dear Aidan, Thank you for your fantastic review! We’re thrilled that you enjoyed your day discovering Tuscany, from the beautiful scenery and wine tasting to the delicious lunch. We’re especially happy that exploring Siena was the highlight of your experience—its history and atmosphere truly make it unforgettable. We hope to welcome you back to discover even more of Tuscany! Arrivederci from Tuscany, The Caf Tour & Travel Team
via Viator
Wonderful day trip, lunch and wine tasting
The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!
Response from the operator: Thank you Sarah for such a generous and detailed review! We’re so pleased that the day gave you the freedom to explore while still feeling well guided throughout. Riccardo and Cristina will be delighted by your kind words, and it’s wonderful to know the wine tasting and lunch added so much to the experience. Warm greetings from Tuscany!
via Viator
Best day in Tuscany
Excellent tour. Special thanks to our bus driver, Alice, and tour guides Fabi and Louisa. Cathedral in Siena worth paying extra. Beautiful scenery, tasty food and wine, shopping lover's dream. Grazie!
Response from the operator: Grazie mille for this lovely review! We’re so pleased that Elis, Fabi, and Louisa helped make the day such a success. Siena clearly made a strong impression, and your words will be very helpful to future travelers considering the Cathedral visit. Thank you again for sharing your experience, and warm greetings from Tuscany!
via Tripadvisor
Wonderful Surprise!
Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!
Response from the operator: This is exactly the kind of experience we love to hear about, sharing a long table with new friends, tasting local wines, enjoying authentic Italian food, and even taking a few delicious souvenirs home! We’re also so happy that Siena, its Cathedral, and its history left such a strong impression. Thank you for letting us be part of such a memorable day in Tuscany! See you soon, Zoe!
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
- Price range
- $40 to $79
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 64
- Verdict
- Strongly Recommended
Why this scores 72
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting cost?
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Prices start at $40 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 San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 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 Florence is not rushed.
Is San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting worth it?
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It holds an Outty Ranking of 72 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.5/5 across 182 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 San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting?
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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 San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting suitable for kids and families?
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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?
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Around 64 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 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?
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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?
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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?
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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?
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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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