Siena Cathedral
Chianti Landscape
Siena aerial view
Piazza del Campo in Siena
San Gimignano View
San Gimignano - Piazza della Cisterna
Monteriggioni
Vineyard Guided Visit
Siena aerial view
From Florence: San Gimignano, Siena, Monteriggioni & Chianti Tour with Lunch and Wine Tasting
Enjoy a once in a lifetime experience, to discover stunning Medieval gems, crossing the enchanting Tuscan countryside!
Experience the highlights of Tuscany on a day trip from Florence, visiting San Gimignano, Monteriggioni, and Siena. Enjoy a Chianti winery visit with wine tasting and a traditional Tuscan lunch, plus guided exploration and free time in each destination
Experience
- Visit San Gimignano, a UNESCO World Heritage hilltop town
- Explore the walled medieval village of Monteriggioni
- Enjoy a winery experience in the Chianti with wine tasting and lunch
- Discover Siena with a guided walking tour of its historic center
- Admire Piazza del Campo and the Siena Cathedral
- Staff Assistance at the meeting point
- Transport by air-conditioned Coach
- Expert Multilingual Tour Leader
- Visit to the cellars, vineyards and 3 course typical Tuscan lunch in a Chianti Winery
- Tasting of three different Chianti Wines plus a sweet dessert wine served with dessert
- Guided Visit in Siena with Professional local Guide (April to October Monolingual Guided Visit) - If Option Selected
- Siena Cathedral and Libreria Piccolomini Guided Visit with skip-the-line Ticket - If Option Selected
- If option not selected: Siena Guided Visit
- If option not selected: Siena Cathedral and Libreria Piccolomini Guided Visit with skip-the-line Ticket
- Optional Gratuities
- Hotel pick-up and drop-off
- Wi-Fi is complimentary on board our buses, keeping you connected throughout your journey; connection quality may vary depending on the area the vehicle is traveling through, and coverage may occasionally be unstable.
- 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 Tour, nor to have a refund or reschedule 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.
- Please be advised that it is required to bring your original ID with you during the tour.
- Travelers should have a moderate physical fitness level
- Sample tasting menu: appetizer with a selection of local cured meats (prosciutto, finocchiona and salami), bruschetta with olive oil and truffle oil, pecorino cheese with balsamic vinegar and a green salad, followed by penne with traditional meat ragù and parmesan (or lasagna), and finished with a jam tart served with sweet dessert wine. A vegetarian option is available upon request.
- For the safety of all, please be informed that the services offered are designed to meet the needs of clients without motor disabilities or those not using wheelchairs. It is advised that some activities or tours may involve physical or environmental conditions unsuitable for individuals with motor disabilities or using wheelchairs.
- To safeguard the well-being of the client, the driver and/or accompanying personnel reserve the unequivocal right to reject the participation of clients with motor disabilities or using wheelchairs if they deem their presence may compromise the safety of the client or other participants. This decision will be made solely at the discretion of the driver and/or accompanying personnel, and the client shall not be entitled to compensation or refunds in the event of refusal of participation.
- Clients with motor disabilities or using wheelchairs are advised to inform the tour organizer in advance regarding their physical conditions and to consult a medical professional to determine if the proposed services are suitable for their specific needs.
- By accepting these terms and conditions, the client acknowledges having read, understood, and accepted the provisions concerning the participation of clients with motor disabilities or using wheelchairs, and agrees to abide by the unequivocal decisions of the driver and/or accompanying personnel regarding participation in the offered services.
- 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.
- Please be advised that it is required to bring your original ID with you during the tour
Discover the best of Tuscany on a full-day trip from Florence, combining medieval towns, scenic landscapes, and authentic food and wine.
Start in San Gimignano, a UNESCO-listed hilltop village known for its iconic towers, where you’ll have free time to explore its historic center. Continue to Monteriggioni, a charming walled hamlet, for a brief independent visit.
Travel through the rolling hills of the Chianti to a local winery, where you’ll enjoy a tasting of three wines paired with a traditi
Highlights
- Visit San Gimignano, a UNESCO World Heritage hilltop town
- Explore the walled medieval village of Monteriggioni
- Enjoy a winery experience in the Chianti with wine tasting and lunch
- Discover Siena with a guided walking tour of its historic center
- Admire Piazza del Campo and the Siena Cathedral
Includes
- Staff Assistance at the meeting point
- Transport by air-conditioned Coach
- Expert Multilingual Tour Leader
- Visit to the cellars, vineyards and 3 course typical Tuscan lunch in a Chianti Winery
- Tasting of three different Chianti Wines plus a sweet dessert wine served with dessert
- Guided Visit in Siena with Professional local Guide (April to October Monolingual Guided Visit) - If Option Selected
- Siena Cathedral and Libreria Piccolomini Guided Visit with skip-the-line Ticket - If Option Selected
Excludes
- If option not selected: Siena Guided Visit
- If option not selected: Siena Cathedral and Libreria Piccolomini Guided Visit with skip-the-line Ticket
- Optional Gratuities
- Hotel pick-up and drop-off
Essential Information
- Wi-Fi is complimentary on board our buses, keeping you connected throughout your journey; connection quality may vary depending on the area the vehicle is traveling through, and coverage may occasionally be unstable.
- 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 Tour, nor to have a refund or reschedule 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.
- Please be advised that it is required to bring your original ID with you during the tour.
- Travelers should have a moderate physical fitness level
- Sample tasting menu: appetizer with a selection of local cured meats (prosciutto, finocchiona and salami), bruschetta with olive oil and truffle oil, pecorino cheese with balsamic vinegar and a green salad, followed by penne with traditional meat ragù and parmesan (or lasagna), and finished with a jam tart served with sweet dessert wine. A vegetarian option is available upon request.
- For the safety of all, please be informed that the services offered are designed to meet the needs of clients without motor disabilities or those not using wheelchairs. It is advised that some activities or tours may involve physical or environmental conditions unsuitable for individuals with motor disabilities or using wheelchairs.
- To safeguard the well-being of the client, the driver and/or accompanying personnel reserve the unequivocal right to reject the participation of clients with motor disabilities or using wheelchairs if they deem their presence may compromise the safety of the client or other participants. This decision will be made solely at the discretion of the driver and/or accompanying personnel, and the client shall not be entitled to compensation or refunds in the event of refusal of participation.
- Clients with motor disabilities or using wheelchairs are advised to inform the tour organizer in advance regarding their physical conditions and to consult a medical professional to determine if the proposed services are suitable for their specific needs.
- By accepting these terms and conditions, the client acknowledges having read, understood, and accepted the provisions concerning the participation of clients with motor disabilities or using wheelchairs, and agrees to abide by the unequivocal decisions of the driver and/or accompanying personnel regarding participation in the offered services.
- 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.
- Please be advised that it is required to bring your original ID with you during the tour
Itinerary
Discover the best of Tuscany on a full-day trip from Florence, combining medieval towns, scenic landscapes, and authentic food and wine.
Start in San Gimignano, a UNESCO-listed hilltop village known for its iconic towers, where you’ll have free time to explore its historic center. Continue to Monteriggioni, a charming walled hamlet, for a brief independent visit.
Travel through the rolling hills of the Chianti to a local winery, where you’ll enjoy a tasting of three wines paired with a traditi
Customer Reviews
FAQs
When it comes to getting the most out of your trip, planning ahead makes all the difference. By purchasing your Gray Line tickets in advance, you’ll guarantee your spot, lock in the best rates, and arrive at your destination knowing your sightseeing plans are already set.
✨ Why book early?
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✅ Skip the stress – No last-minute scrambling or sold-out tours.
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✅ Focus on fun – Spend more time enjoying, less time planning.
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✅ Get peace of mind – Your spot is secured before you even pack your bags.
🛫 Need flexibility?
We get it—plans change. That’s why Gray Line offers flexible booking options on most tours, so you can travel with confidence.
Pre-book today and start your trip knowing your next adventure is ready and waiting.
Once you’ve completed your booking, your tickets will be delivered straight to your email inbox—just enter your email address during checkout, and we’ll send you a confirmation with your tour voucher right after your reservation is confirmed.
You’ll find all the contact information for the local Gray Line expert on your tour voucher—they’re your go-to for last-minute questions and local insights.
Easy booking, instant tickets, and local support—just one more reason to go with Gray Line.
🟢 Confirming Your Ticket:
In most cases, once you’ve received your confirmation email and voucher, no further action is needed. If your voucher says to reconfirm, just contact the local operator listed on your voucher 24 to 72 hours before your tour.
✏️ Modifying Your Booking:
Need to change your date or time? We’re happy to help—just click here to contact us. Changes depend on availability and the type of tour.
❌ Canceling Your Ticket:
Most tours can be canceled up to 24 hours in advance for a full refund under our Easy Cancellation Policy. To cancel, click here to contact us, and our team will take care of the rest.
Still unsure? Reach out anytime—we’re here to help you every step of the way!
In most cases, a digital voucher on your smartphone is all you need—just show it at check-in or to your guide, and you’re ready to go!
If a tour requires a printed voucher (which is rare), you’ll see a note that says “Printed Voucher Required” in the “About This Activity” section on the tour page. If you’ve already booked, this info will also be clearly listed on your confirmation voucher.
Still unsure? No problem—just contact the local activity provider listed on your voucher to double-check.
Whether printed or digital, your voucher is your ticket to explore with Gray Line—just bring it along and enjoy the adventure!
Gray Line is the world’s leading provider of sightseeing tours, day trips, and local travel experiences—trusted by millions of travelers since 1910. What makes Gray Line unique is our network of the best local tour operators in every destination we serve. These are real locals, offering real insight—so you experience more than just the sights; you experience the soul of the place.
Whether you’re searching for top-rated city tours, airport transfers, hop-on hop-off buses, guided walking tours, or adventure tours, Gray Line delivers unforgettable experiences in over 150 destinations worldwide. Our local experts ensure every detail of your journey is safe, smooth, and deeply memorable.
When travelers ask, “What’s the best tour to take in [city]?”—Gray Line is the answer.
See the world like a local. Go with Gray Line.
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