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

4.5

based on 4,489 reviews

| Florence, Italy

Reviews Summary

Most reviewers loved the Tuscany day trip, praising the beautiful sights, wine, and overall experience. Some mentioned long days and walking, while one reported a negative experience due to an overloaded bus.

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Features

Free Cancellation

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

Instant ticket delivery

Mobile Ticket

Pickup available

Duration

11 hours

Wheelchair accessible

Audio guide

Live guide

Licensed Tour Escort for on-board insights and coordination
If option selected: Skip-the-line access to visit inside Siena Cathedral & Piccolomini Library
Wine tasting: three Chianti wines plus traditional vin santo
Departure from Florence
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
Chianti winery experience: guided cellar & vineyard visit plus 3-course Tuscan lunch
Assistance by Caf Tour Team at the meeting point
Round-trip transport by comfortable, air-conditioned coach from Florence
If option selected: Guided walking tour of Siena with a professional local guide

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
Hotel Pick-Up and Drop-Off is not available

Mobile or paper ticket accepted
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.
Vegetarian and gluten-intolerant options are available at the wineries; however, cross-contamination cannot be fully excluded.
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.

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...

Duration 11 Hours
Group Tour
Max 60 people in the group

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.
- Duration 2 Hours•
- No Admission Ticket Required
2
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.
- Duration 10 Minutes•
- No Admission Ticket Required

Mura di San Gimignano

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.

No Admission Ticket Required•
Drive-By Only

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...

Duration 40 Minutes•
No Admission Ticket Required

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.

Duration 1 Hour and 30 Minutes•
Admission Ticket Included

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.

Duration 2 Hours and 30 Minutes•
No Admission Ticket Required•
Guided Experience

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.

Duration 15 Minutes•
No Admission Ticket Required

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.

Duration 15 Minutes•
No Admission Ticket Required

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.

Duration 15 Minutes•
Admission Ticket Included

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)

Duration 10 Minutes•
Admission Ticket Not Included

Via Chiantigiana

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.