San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

based on 3009 reviews

Duration:11 hours (approx.)
Location: Florence, Tuscany

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Discover the timeless allure of Tuscany on an immersive full-day journey! Step into the enchanting past of San Gimignano, often dubbed the "Manhattan of the Middle Ages" for its towering skyline. Traverse its cobblestone streets, steeped in history, and soak in the panoramic views of this captivating Tuscan hill village.

Next, delve into the cultural richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy.

Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany's heart.

Please note that the order of the visits may change

(*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

WHAT'S INCLUDED

WHAT TO EXPECT

1.
Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery.
2.
Piazza della Cisterna is a charming medieval square situated in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square takes its name from the ancient cistern located at its center. The triangular-shaped square is paved with medieval stones and exudes a timeless atmosphere. With its well-preserved medieval architecture and unique charm, Piazza della Cisterna stands as a captivating focal point within the UNESCO World Heritage site of San Gimignano.
3.
These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The "Mura" offer a scenic stroll along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside.
4.
A short distance from San Gimignano you will visit the charming historical hamlet of Monteriggioni (*), an amazing small medieval village enclosed by its famous walls, which remained standing to this day: free time for inside visit. (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier.
5.
From Monteriggioni, crossing the gently Chianti rolling hills, a short ride will take you to a cozy Winery, where you can relax and enjoy the fantastic world of Chianti with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course with “zero food miles” products which ends with "cantucci e vin santo".
6.
Later on, getting to Siena, you will meet your professional local guide who will lead you on a comprehensive guided tour of the historic center. Then strolling along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, passing through Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point,
7.
Our Siena Guided Visit starts from Piazza Salimbeni where Palazzo Salimbeni is located. The ancient Palace hosts the first and oldest Bank in the world.
8.
Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point
9.
you will get to the spectacular Cathedral of the 12th century (inside visit if option selected), of which you can admire the magnificent architecture and the splendor of the polychrome marbles. You will also have some free time to end your perfect day enjoying the unique atmosphere of this amazing city, before the return to Florence in the evening. Please note that the order of the visits may change
10.
Only if cathedral entrance option is selected - The Piccolomini Library, housed within the Duomo di Siena, is a Renaissance gem adorned with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, creating a cultural and artistic treasure within the Siena Cathedral.
11.
Coming back to Florence you'll drive through the Chiantigiana road, a scenic route that winds through the picturesque Chianti region. This iconic road takes travelers through rolling hills adorned with vineyards, olive groves, and charming villages. Along the way, you'll encounter classic Tuscan landscapes, medieval castles, and renowned wineries producing the world-famous Chianti wine. The journey along Via Chiantigiana offers a delightful blend of cultural richness, culinary delights, and breathtaking views, making it a popular route for those seeking an authentic Tuscan experience.

ADDITIONAL INFO

• 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
• A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
• 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.
• From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
• 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.
• Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.

CANCELLATION POLICY

Posted By : Z6640FRericg
Loved it. Fabiana (guide) was wonderful, knowledgeable, kind and responsive. Mossimo (driver) was smooth and safe. It’s a long day but it is at a relaxed pace with plenty of time to sit at a cafe and recharge, or shop. And of course, the scenery, wine, food and people were absolutely lovely. Wear good walking shoes. Bring a water bottle.
Rating : full ratings
Posted On : 2024-07-01 16:57:39

Posted By : 438paulaf
Our tour guide Fabiana was so amazing and thorough. She made the entire tour a pleasant experience. She was very knowledgeable and kind. Our driver Massimo was an incredible driver and also friendly and kind. Overall, just a great experience and I highly recommend this tour.
Rating : full ratings
Posted On : 2024-07-01 14:10:56

Posted By : U1865HObrookew
Such a great way to see a few of the towns in tuscany, I thoroughly enjoyed my time! Fabiana was a great host; she was super warm and welcoming to everyone. The wine tour was a little underwhelming, but still lovely food - just not as much wine as I was anticipating. Thanks so much!
Rating : full ratings
Posted On : 2024-07-01 12:04:29

Posted By : Geoff M
We loved the tour, such fantastic scenery and great change up from busy cities. Riccardo was a great tour guide very informative. And compliments to Sergio on his driving skills.
Rating : full ratings
Posted On : 2024-07-01 12:00:00

Posted By : Skyler_D
This tour is good for if you wanna get out Florence and visit the little cities around. You get to go and explore yourselves which is what we liked. The lunch section was just okay but was cool to see a winery.
Rating : full ratings
Posted On : 2024-06-30 19:51:37

Posted By : Damian_W
It’s a long day ! Be prepared. We did 20,000 steps so take plenty of water. All sites worth visiting. Good lunch , entertainingly delivered by the host. We’d booked the walking tour of Siena and the cathedral - definitely do both. But we had an hour in Siena before the tour so spent that in a lovely cafe, Nannini, relaxing - good choice ! Excellent tour leader Martha.
Rating : full ratings
Posted On : 2024-06-30 05:44:31

Posted By : L52ZZkennyc
Great wine trip. Good host. Wine was amazing. Snacks as well. Great scenic bus ride as well. Book this trip if you get the chance.
Rating : full ratings
Posted On : 2024-06-29 13:28:41

Posted By : Pizzalover204
We were a family group of 8 adults and 5 kids. The tour guides were Very organized, patient and kind. Thank you Marta and Luce! Plenty of time to roam yourself. It didn’t feel like a constricted tour at all.
Rating : full ratings
Posted On : 2024-06-29 12:55:10

Posted By : Explorer771738
Beautiful places, nice guides, well organized trip. Lunch was great at the vineyard. Thats all thank you very much 😊😊😊😊
Rating : full ratings
Posted On : 2024-06-29 12:54:27

Posted By : dbarrasso
Our tour was well organised and our tour leader Martha kept us on track. She was very nice and quite informative.
All the towns were just gorgeous. So much history. The wine tasting was also a pleasant surprise. Very fine wine and a nice lunch.
A long but very good day!!!
Rating : full ratings
Posted On : 2024-06-29 12:53:54