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

Stop At: San Gimignano, San Gimignano, Tuscany

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.

Duration: 2 hours

Stop At: Piazza della Cisterna, Piazza Della Cisterna, San Gimignano Italy

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.

Duration: 10 minutes

Pass By: Mura di San Gimignano, Porta San Giovanni, 53037, San Gimignano Italy

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.

Stop At: Monteriggioni, Monteriggioni, Tuscany

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.

Duration: 40 minutes

Stop At: Chianti Road, Italy

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".

Duration: 1 hour 30 minutes

Stop At: Siena, Siena, Tuscany

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,

Duration: 2 hours 30 minutes

Stop At: Piazza Salimbeni, 53100, Siena Italy

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.

Duration: 15 minutes

Stop At: Piazza del Campo, 53100, Siena Italy

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

Duration: 15 minutes

Stop At: Duomo di Siena, Piazza del Duomo 8, 53100, Siena Italy

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

Duration: 15 minutes

Stop At: Biblioteca Piccolomini, Piazza del Duomo, 53100, Siena Italy

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.

Duration: 10 minutes

Pass By: Via Chiantigiana, Firenze FI, Italy

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.

Sample Menu

• Appetizer - Cold cuts ( prosciutto, finocchiona, salami ) Bruschetta olive oil and truffle oil; Pecorino Cheese with balsamic vinegar and green salad
• Main Course - Penne with meat ragout and parmesan cheese
• Dessert - Homemade tart with jam and vinsanto
• Wine Tasting - Wine Tasting of 3 different Tuscan wines

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

• 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

• Not wheelchair accessible
• Stroller accessible
• Near public transportation
• Infant seats available
• Travelers should have a moderate physical fitness level
• 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.
• This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
• This tour/activity will have a maximum of 50 travelers
• Confirmation will be received at time of booking

Piazzale Montelungo, Firenze FI, Italy

08:00 AM

Returns to original departure point

You can present either a paper or an electronic voucher for this activity.

11 hours