San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

4.5
(4,701 reviews)
Florence, Italy

11 hours (approximately)
Offered in: English and 1 more

Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence.

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

Siena Cathedral and Libreria Piccolomini entrance with guided visit (if option selected)
Comfortable G.T. Coach transport from Florence in a modern, air-conditioned bus
Immersive journey led by a Licensed Multilingual Tour Leader (English & Spanish)
If option selected: from November to March the visit in Siena can be bilingual (English and Spanish)
If option selected: April to October, visit in Siena is monolingual. Language selected while booking
Dedicated Caf Tour & Travel Staff Assistance at the meeting point
Chianti Winery experience: Guided Cellar visit plus 3-course Tuscan lunch & 3 Chianti Wines Tasting
Guided tour in Siena with Earphones provided (if option selected)
From November to March, the itinerary does not include the stop at Monteriggioni

Meeting and pickup

Meeting point
Piazzale Montelungo

Check in time: 07:45am - Montelungo Square, 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.

End point
This activity ends back at the meeting point.

Itinerary

Duration: 11 hours (approximately)
  • 1
    San Gimignano

    Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.

    2 hours Admission ticket free
  • Piazza Della Cisterna (Pass by)

    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.

    Admission ticket free
  • Mura di San Gimignano (Pass by)

    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.

    Admission ticket free
  • 2
    Monteriggioni

    Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) 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 Admission ticket free
  • 3
    Siena

    Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace.

    2 hours 30 minutes Admission ticket free
  • 4
    Piazza del Campo

    Piazza del Campo is the main square of Siena, famous for its distinctive shell shape and elegant brick pavement. Surrounded by historic buildings, it is home to the Palazzo Pubblico and the Torre del Mangia. It is also the setting for the famous Palio di Siena, a historic horse race between the city’s districts.

    15 minutes Admission ticket free
  • 5
    Duomo di Siena

    Cathedral Entrance and inside guided visit only if option selected - officially known as the Cathedral of Santa Maria Assunta, is a stunning medieval cathedral in Siena. Renowned for its distinctive Gothic architecture, the cathedral showcases a magnificent facade adorned with intricate sculptures. Inside, visitors can marvel at remarkable works of art, including frescoes, mosaics, and statues by renowned artists like Donatello and Michelangelo. The cathedral's breathtaking interior also features a striking marble pavement and a magnificent Piccolomini Library.

    30 minutes Admission ticket included
  • 6
    Biblioteca Piccolomini

    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.

    15 minutes Admission ticket included

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.
Supplied by CAF Tour and Travel - Gray Line Florence
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Tags

Day Trips
Wine Tastings
Full-day Tours
Bus Tours
Cultural Tours
Wine Tours
Food & Drink
Excellent Quality
Top Product
Low Supplier Cancellation Rate
Low Last Minute Supplier Cancellation Rate
Curated Catalog
Short term availability

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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