Available languages
10 hours 30 minutes
Mobile ticket
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Specialized infant seats are available
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
May be operated by a multi-lingual guide
Please note that the given order of the visits may change
Please inform us of any food intolerance or allergy in advance
Kindly note that the Semi independent option does not include the professional guide in Siena
LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
For a full refund, cancel at least 24 hours before the scheduled departure time.
Free time in San Gimignano and Monteriggioni Medieval towns
Siena tour with professional guide with Headsets (not included in the semi independent option)
Visit to a charming wine estate in the Chianti area with tasting of up to 2-3 Chianti wines
Expert multilingual Tour Leader
Sampling of wines, extra-virgin olive oil and regional products
Journey by fully-fitted GT Coach with Free Wifi on board
Gratuities
Hotel pickup and drop-off
Siena Cathedral tickets (approx. 7€ pp)
Lunch
The tour starts from Florence and leads you to the atmospheric Medieval gem of Monteriggioni. It was built in 1203 and became a strategic garrison town with its 14 towers, Dante called it the “ring-shaped citadel”. Here you can steep yourself in the past and prepare yourself for the wonders of Siena . Here your local guide will reveal to you its main beauties: the stunning Piazza del Campo, an open-air fish bowl, surrounded by softly-washed Siena stone architectural masterpieces. It really is a showpiece place, worth lingering in and drinking in the richness of the past. Visit Piazza del Duomo and be impressed by the imposing Cathedral, one of the finest achievements of Italian Gothic. Before leaving Siena you will be served a light lunch in a cozy restaurant where, together with genuine Tuscan products, you will savour traditional pastries. After your free time for lunch in Siena, continue on to San Gimignano: the home of the renowned Vernaccia wine. This Medieval town is listed as a UNESCO World Heritage Site, and once you're there you'll see why. The secret lies in its soaring towers that seem like skyscrapers! It is a jewel of art and architecture and also boasts one of the best ice-creams in the world! Here you're free to stroll around or just stop and take it all in. Next, Chianti calls. You will visit a rustic wine estate where, after drinking in the landscapes, you can taste and sip quality wines and try the plonk along with oils and local products. This is a tour made for the spirit and the flesh. A perfect way to mix quality culture and cuisine.
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
All inclusive tour -Portuguese: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
2,455 reviews
Total reviews and rating from Viator & Tripadvisor
Paul H,
Nov 19, 2025
- Review from Viator
Beautiful countryside and interesting places to see. The reason rating not higher was it combined 3 languages on same tour Made it complicated. Winery was a commercial operation. Hoped the wine tasting to be overlooking the Tuscan hills
irenemX3686JQ,
Nov 17, 2025
- Review from Tripadvisor
The tour was very complete and interesting. Gabriele, our companion, was attentive throughout, and the driver, Cozimo, made a very comfortable journey. The villages visited were beautiful and the wine tasting was especially remarkable. Highly recommended.
GurpreetS1355,
Nov 17, 2025
- Review from Tripadvisor
Had a great time on the tour. Definitely well worth the money for a full day. Our driver, Qassimo, and the guide, Gabriele, ensured we had a safe and informative drive on the way to the different locations, not to mention the recommendations and other suggestions over the course of the tour. Had to contact the Ciao Florence helpline over call because I misheard the guide's directions about the pickup at Siene, and they were super responsive as well. Excellent overall and would surely avail their services again.
223raphaelag,
Nov 17, 2025
- Review from Tripadvisor
Great walk The guide Gabriel, quite attentive and patient. Gave to know a little bit of each city and have a good wine tasting. We adore
Tour830221,
Nov 17, 2025
- Review from Tripadvisor
The experience was unforgettable. All very well organized, allowing us to enjoy what makes each of the small towns special. Gabrielle accompanied us and guided us very well throughout the day. Very willing and nice. We recommend it!
Karen C,
Nov 17, 2025
- Review from Tripadvisor
Great tour with Gabrielle and Cosimo (driver). Covered so many different sites and saw incredible scenery. Well worth the money.




andreaaP7318SM,
Nov 16, 2025
- Review from Tripadvisor
Excellent whole tour!! Sebastian guide 10 points.. and the impeccable driver!! Beautiful experience that gave us a great day. I recommend it
estelaelenae,
Nov 16, 2025
- Review from Tripadvisor
Interesting and beautiful Siena and San Gimignano, the visit to the winery a disappointment and the other village irrelevant, should be reduced only to the two villages



unaia375,
Nov 16, 2025
- Review from Tripadvisor
Everything super good! Gabriele guides superrr nice and explaining everything and Zeny driver super well. Lovely villages.




siobhianj,
Nov 15, 2025
- Review from Tripadvisor
The tour was packed with a lot to see and experience. Gabriele, our tour guide did an excellent job to manage the activities while being warm and approachable. We did the tour with our toddler who enjoyed running around exploring the towns. It was an excellent day trip!!!
Operated by Ciao Florence Tours Srl