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

Location Florence, Tuscany, Italy
$94.81
This is an experience gift voucher. The recipient will book the experience after they redeem the gift voucher.

Overview

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 & vin santo. 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
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The experience offers several options. This price includes:

English-Shared Round Transport
Lunch
Shared Round Transport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Tour guide
Language: English
Human tour guide
Duration: 11 hours

The experience offers several options, check yours above
  • Round-trip transport by comfortable, air-conditioned coach from Florence
  • Assistance by Caf Tour Team at the meeting point
  • Chianti winery experience: guided cellar & vineyard visit plus 3-course Tuscan lunch
  • If option selected: Guided walking tour of Siena with a professional local guide
  • Wine tasting: three Chianti wines plus traditional vin santo
  • If option selected: from April to October monolingual guided visit in Siena
  • If option selected: Skip-the-line access to visit inside Siena Cathedral & Piccolomini Library
  • Licensed Tour Escort for on-board insights and coordination
  • From November to March, the itinerary does not include the stop at Monteriggioni
  • Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission

Meeting point
Open location in Google Maps
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.
Return details
Open location in Google Maps
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.

  • 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.
  • Piazza Della Cisterna
    The atmospheric heart of San Gimignano, framed by tower-houses and a medieval stone well that anchors the square. A short, curated stop for photos and storytelling that brings the town’s merchant past to life.
  • Glide past the 14th-century fortifications and the most iconic gate, imagining pilgrims and traders entering centuries ago. Your tour leader shares context and highlights so you can appreciate the engineering and defense of a Tuscan walled city. (pass by)
  • 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
  • Strada Statale 222 Chiantigiana
    Travel the legendary wine route through rolling vineyards, stone farmhouses, and cypress-lined ridges—classic Tuscany in every direction. Stop at a welcoming Chianti winery for a tasting of three wines and a farm-to-table 3-course lunch, ending sweetly with cantucci e vin santo.
  • 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.
  • Piazza Salimbeni
    Admire refined Renaissance architecture and hear how the world’s oldest operating bank shaped Siena’s wealth and culture. It’s a concise stop with rich history and elegant façades perfect for quick photos.
  • Piazza del Campo
    Stand in Siena’s shell-shaped stage, home to the legendary Palio horse race, and take in Palazzo Pubblico and Torre del Mangia. Your guide unpacks centuries of tradition so the square’s drama and design truly resonate.
  • Duomo di Siena
    Gaze at the striped marble exterior, a Gothic marvel that crowns the city; (if option selected) interior visit to admire polychrome floors and masterpieces. A powerful highlight that pairs art history with unforgettable visuals.
  • Biblioteca Piccolomini
    Step into a jewel box of vivid Pinturicchio frescoes and illuminated manuscripts that glow with Renaissance color. A quick but dazzling stop that rewards art lovers and casual visitors alike. (if cathedral option selected)
  • Return along vineyard-draped hills and ancient hamlets, the perfect finale for golden-hour photos across the Tuscan countryside. A smooth, scenic drive back to Florence rounding off a day of towers, wine, and medieval splendor. (pass by)

  • 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 or no show 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.
  • 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.
  • 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.

  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • 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.
    • How it works?
    01 — You choose from 10,000+ experience gifts
    02 — We deliver the eVoucher or the Physical box to the recipient
    03 — Recipient books the experience and creates unforgettable memories!

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

    Location Florence, Tuscany, Italy
    $94.81
    This is an experience gift voucher. The recipient will book the experience after they redeem the gift voucher.
    Packaging & Delivery
    How it works?
    01 — You choose from 10,000+ experience gifts
    02 — We deliver the eVoucher or the Physical box to the recipient
    03 — Recipient books the experience and creates unforgettable memories!
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