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

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     

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.

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.

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.

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.

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”.

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,

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.

Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point

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

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.

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.

• 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.
• Please be advised that it is required to bring your original ID with you during 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.

• Tour in English
  Add
  Lunch
  Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
  Not included: Cathedral admission
• Spanish-Shared Round Transport
  Add
  Lunch
  Shared round Trasport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
  Not included: Siena Guided Visit and Cathedral admission
• Tour in Spanish
  Add
  Lunch
  Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
  Not included: Cathedral admission
• English-Shared Round Transport
  Add
  Lunch
  Shared Round Transport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
  Not included: Siena Guided Visit and Cathedral admission
• English Tour with Cathedral
  Add
  Lunch
  Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
• Spanish Tour with Cathedral
  Add
  Lunch
  Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission

• Siena Cathedral interior Guided Visit including entrance fee (if option selected)
• Licensed Tour Leader with live commentary on board
• from April to October – monolingual Visit in Siena
• 3 course set-menu typical Tuscan lunch in a Chianti Winery
• Transport by G.T. air-conditioned coach
• Local guide in Siena (if option selected)
• Tasting of three different Chianti Wines, extra virgin olive oil & “vin santo”

• Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
• From November to March, the itinerary does not include the stop at Monteriggioni

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• Check-in time and Meeting Point:
at 7:45 am at Piazzale Montelungo, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour – Gray Line logos.

How to reach the meeting point from Santa Maria Novella Station Square:
Take “Via Valfonda” (Valfonda street) and go straight on at the end of the street, until you see the Fortress (Fortezza da Basso). Cross the street in front of you and keep your left side, until you see on the right side Piazzale Montelungo (big square with car and Bus parking)

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.

Please be advised that it is required to bring your original ID with you during the tour.

– For small groups, up to 8 pax, the Tour will be by Minivan and the Tour escort service will not be provided. The remaining services will be as scheduled.
– It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship.

• Our Contacts:
Agency address: via dei Tavolini 15red – 50122 Firenze – Phone +39 055 29.55.72 or +39 055 28.32.00 – Whatsapp: +39 3458025842
email address: tours@caftours.com

Please be advised..

• This Tour is Provided by CAF Tour and Travel.
• Tour Timezone & Starts at Europe/Rome.
• Mobile or paper ticket accepted.
• For a full refund, cancel at least 24 hours before the scheduled departure time.
• This Tour is Rated 4 Stars based on 3556 valid reviews on VIATOR.
• Minimum 1 Travelers is required to book.
• Maximum 8 Travelers is accepted for booking.