Tours/Florence/Siena, San Gimignano and Chianti Wines Day Tour from Florence
Viator · group up to 50 pax

Siena, San Gimignano and Chianti Wines Day Tour from Florence

4.6(3,115)Florence1 hour
VIATOR4.4(935)TRIPADVISOR4.8(2,180)

Description

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.

Tour Options

Audio Guided Tour Japanese
  • Historical explanations will be via audio guide (App) in Japanese. A Tour Leader will coordinate and provide lnfo in English.
English With Guided Siena
  • 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
Italian With Guided Siena
  • 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
English with Free Time
  • 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
Spanish With Free Time
  • 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
Audio Guided Tour Korean
  • Historical explanations will be via audio guide (App) in Korean. A Tour Leader will coordinate and provide lnfo in English.
French With Guided Siena
  • 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
Italian With Free Time
  • 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
Portuguese With Guided Siena
  • 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
Spanish With Guided Siena
  • 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
Chinese Audio Guided Tour
  • Audio Guided Tour Chinese: Historical explanations will be via audio guide (App) in chinese. A Tour Leader will coordinate and provide lnfo in English.
Portuguese With Free Time
  • 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
French With Free Time
  • 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

Itinerary

45 min

There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.

60 min

After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).

180 min

Continue to Siena, one of Tuscany’s most beautiful historic cities. Guests who select the Classic Tour option will enjoy a 1-hour guided walking tour with a professional guide, focusing on the city’s main highlights (exterior visits only). Guests with the Semi-Independent option will have approximately 2.5 hours of free time to explore Siena at their own pace.

30 min

During the guided tour, admire Piazza del Campo from the outside, one of Europe’s most stunning medieval squares. Your guide will explain its unique shell shape and its role as the setting of the famous Palio horse race, as well as the exterior of the Palazzo Pubblico and the Torre del Mangia.

Admission not included30 min

The final stop of the Siena visit is the Siena Cathedral, admired from the outside. Learn about this magnificent example of Italian Gothic architecture, renowned for its intricate marble façade.

60 min

After lunch, travel on to San Gimignano, the medieval town famous for its skyline of towers. Enjoy free time to wander through its cobblestone streets, browse local shops, or relax with a coffee in one of the charming squares.

Admission not included15 min

During your free time, you may choose to visit the Collegiata, the town’s main church, known for its well-preserved frescoes and Romanesque architecture (entrance optional).

Admission not included5 min

During your free time in San Gimignano, you may choose to stop at the famous Gelateria Dondoli, an award-winning gelato shop located in the main square. This is a great opportunity to taste some of Italy’s most renowned artisanal gelato (not included in the tour price).

60 min

In the evening, relax on the journey back to Florence, bringing an unforgettable day in Tuscany to a close.

Highlights

Free time in San Gimignano and Monteriggioni Medieval towns
Gran Turismo Luxury bus travel with WiFi on board
Expert multilingual Tour Leader
Visit to a charming Chianti wine estate with tastings of up to 2-3 Chianti wines and regional snacks
Siena tour with professional guide with Headsets (not included in the "+ Free Time" option)

What's included

Included
Free time in San Gimignano and Monteriggioni Medieval towns
Gran Turismo Luxury bus travel with WiFi on board
Expert multilingual Tour Leader
Visit to a charming Chianti wine estate with tastings of up to 2-3 Chianti wines and regional snacks
Siena tour with professional guide with Headsets (not included in the "+ Free Time" option)
Not included
Gratuities
Hotel pickup and drop-off
Siena Cathedral tickets (approx. 7€ pp)
Lunch

Traveller Ratings

4.6
3,115 reviews
5
2,372
4
497
3
152
2
44
1
50

Important Information

  • 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
  • May be operated by a multi-lingual guide
  • Please note that the given order of the visits may change
  • 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

Reviews(3,115)

N
N795IHmatthewg
July 17, 2026
3 Beautiful Tuscan spots with a Nice Chianti.

Overall a great trip, 3 beautiful spots in Tuscany and some lovely wine to try. Host Lion and driver Patrick fantastic throughout. Easy to book and clear instructions for arrival. Only feedback booking through Tiquets is our names were registered as “tiquets customer” with the trip organiser, so caused a little confusion at the start. Monteriggioni is fantastic and could do with a little longer than 30 mins there per the trip to truly take it in. Siena, a nice tour and great spot to find lunch but 3 hours there a little too long and guided pace was a little quick for my pregnant wife. Wine tasting nice and well presented by an entertaining team, but it is very obviously geared to sell more wine (and why not?!) San Gimignano was wonderful, by far our favourite location of the tour and could do with more than the 1.5 hours there to really explore it and see the great views and historical building. No time to climb Torre Grosso. Perhaps 2 in Siena and 2 in SG would be more balanced? Would do again 100%, but would probably skip Siena to prioritise the other spots. Definitely recommend, it was a highlight day of our trip.

K
Krista_D
July 17, 2026
Tuscany Sampler

I went on this tour to see a bit of Tuscany while in Florence. You see many medieval towns and get a wine tasting. It was a great value and the bus was very comfortable.

Z
zarahgraff
July 17, 2026
Great day trip to Tuscany!

Excellent way experience the Tuscan countryside without actually staying there staying there.

L
Lee007jon
July 17, 2026
Fantastic break from the museums!

Fantastic day out in Tuscany (Siena, San Gimignano, Monteriggioni). Lorenza was very engaging providing great information for each stop. The app kept us updated sharing clear instructions & maps for each pick up point. The wine tasting was fun but the wines are very expensive so unfortunately we didn’t buy any. Rafaelo (our driver) was great too!!

L
l0renasu
July 17, 2026
A nice day trip in Sienna and nearabouts

Trip was very punctual, we have visited three cities/villages and a vineyard, I think given time was perfect - not too short, not too long. Our main guide Lorenza was professional, everythin was in english and there were no issues in communication. In Sienna we had another guide, he had a strong italian accent and sometimes it was a bit difficult to understand (however, my girlfriend had no issues whatsoever, so take it with a grain of salt). Overall I think trip is worth the money.

J
jvanscoyoc
July 17, 2026
Beautiful views and stops

Ciao Florence - it was very hot in July but the guide and driver polite and pleasant. It was a nice trip to Tuscany and Chianti regions.

A
ambermR95EF
July 17, 2026
Happy experience

The guide and bus driver were very kind and knowledgeable. The driver was prepared with cold water and the guide was kind and will to help with anything. The amount of time at each stop was perfect.

U
U2303HUdebrap
July 17, 2026
Enjoyed Tuscany Countryside Immensely

We enjoyed the trip quite a lot. Lorenza and Renaldo did a fantastic job getting us to and from all the locations. I think the time spent at each location was just the right amount. The whole trip is quite long but well worth it in my opinion.

P
P5212ZRjacobb
July 17, 2026
Tuscany full day tour

Great tour and friendly personality

9
939gabbyn
July 17, 2026
10/10!!

The tour was amazing! Got to see so many places and our tour guide Leon was fantastic!

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