Siena, San Gimignano, Monteriggioni And Chianti Wine Tasting Tour From Florence

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Tour Information

Key Details

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  • Duration: 11 Hrs
  • Language:
  • Departure Time :
    08:45 AM Times are subject to change due to local traffic conditions.
  • Departure Details :
    Piazzale Montelungo, Firenze FI, Italy
  • Return Details :
    Returns to original departure point
  • Cancellation Policy :
    This activity is non-refundable Tours booked using discount coupon codes will be non refundable.


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.


  • Comprehensive tour by bus/coach
  • Perfect introduction for first-time visitors
  • Informative, friendly and professional guide
  • Enjoy a day away from the hustle and bustle of the city

Know More about this tour


This is a typical itinerary for your exciting day-trip from Florence -

Stop At: Piazza del Campo, Siena, Tuscany

Explore one of the most beautiful squares in Italy. Its shell shape and the stunning Gothic architecture of Palazzo Pubblico are the highlights here. 

Duration: 20 minutes

Stop At: Siena Cathedral, Siena, Tuscany

One of the most beautiful Gothic-style churches in Italy, with its radiant green and white marble decorations

Duration: 15 minutes

Stop At: Centro Storico di Siena, Siena, Tuscany

Visit Siena, and follow your local guide to the suggestive Piazza del Campo, where the magnificent Palazzo Pubblico stands, with its Torre del Mangia. Visit Piazza del duomo and be impressed by the imposing Cathedral.

Duration: 2 hours

Pass By: Chianti Road, Tuscany

Take in breathtaking views of the Chianti countryside as you travel from one destination to the other. This whole region is the perfect place to get away from all the hustle and bustle. 

Stop At: Historic Centre of San Gimignano, San Gimignano, Tuscany

This place is famous for its white wine, the world-renowned Vernaccia, and its skyscrapers, which are also declared a World Heritage Site by UNESCO! The visit is free for independent sightseeing, strolling around the narrow streets and admiring the relaxing landscape.

Duration: 1 hour

Stop At: Monteriggioni, Monteriggioni, Tuscany

Witness the medieval hilltop gem, with its still intact walls. Here you can drink in history and relive the atmosphere of olden times.

Duration: 1 hour

Then, after all the exploring, end your visit with a Chianti winery where you savor the best of Italian wines!


Journey by fully-fitted GT Coach

Expert multilingual escort

Siena tour with professional guide (not included in the semi independent option)

Visit to a rustic wine estate in the Chianti area with wine tasting

Sampling of wines, extra-virgin olive oil and regional products

Free visit of San Gimignano and Monteriggioni

Entry/Admission - Chianti Road



Hotel pickup and drop-off

Siena Cathedral tickets


Additional Info

Confirmation will be received at time of booking

Not wheelchair accessible

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

Stroller accessible

Service animals allowed

Near public transportation

Infants must sit on laps

Infant seats available

No heart problems or other serious medical conditions

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, German, 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: GERMAN: Monday - min 2 pax FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax

Travelers should have a moderate physical fitness level

This experience requires good weather. If its canceled due to poor weather, youll be offered a different date or a full refund

This tour/activity will have a maximum of 63 travelers

Traveler Reviews

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  • 20-Nov-2022

    I just want to thank Roberta and the driver for this very organized trip that was on time on each stop. And specifically Roberta for her perfect explanation and informations about all the destinations her English, Spanish, Italien and French. We had a wonderful day today on the 20/11/2022 Best regards Nelly

  • 16-Nov-2022

    I have done this tour several times with various family, friend and loved ones. The Siena, San Gimignano and Monteriggioni were fantastic, as was the guide, but the Chianti tour this time was terrible. We have been to some incredible vineyards in Tuscany as part of this tour for years, so I was so disappointed to be brought somewhere that was akin to a factory - and in a very flat part of what is a stunning and undulating part of Italy. The wines were terrible, we were shuffled in/out for an hour and it felt like a tourist trap.

  • 13-Nov-2022

    Siena and San Gimignano were both great stops. The wine tasting was a little rushed. It was a full day of tours.

  • 12-Nov-2022

    The tour was well organize. They even called us because we were to clise ti rhe time for the bus to leave. The guide guy was really funny .My favorite city was san giminiano(a true medivieal city and so pretty).

  • 12-Nov-2022

    This WAS A FULL DAY ! and extremely enjoyable. Importantly, the tour got us into the smaller towns in Italy and gave us enough time to explore each of them. We found a wonderful, small, family owned/run restaurant in Siena with absolutely amazing food and service that treated you like family

  • 09-Nov-2022

    The cathedral in Siena and the tour there as well as the wine tasting. Both were exceptionally good. The medieval towns were a nice historical perspective. Thanks

  • 08-Nov-2022

    Well organized, knowledgeable with a good English guide, picturesc. On the negative side there was a poor description of the location of the startinng trip.

  • 08-Nov-2022

    I recommend this tour to everyone who is visiting Florence. The bus very comfortable and the tour very punctual. The ride very pleasant and our tour guy “ Sandro” has a lot of knowledge and his great personality made our tour a blast. This tour was unforgettable. We did it in my husband’s birthday Sandro was making sure that his celebration’s memories will last forever. The wine tasting and lunch were absolutely delicious.

  • 07-Nov-2022

    Disappointed that bus parked so far from several of the sites we visited. First 2 towns had difficult hills to walk. Had I known I would not have chosen this tour. However, the trip was very well organized in English & Italian. Guides were very nice & knowledgeable. Winery was new & beautiful with ample tastings. Tuscany (final stop) was just beautiful & worth the tour.

  • 30-Oct-2022

    Let me start by saying that San Gimignano was our favorite spot...everyone was nice, smiled and the gelato was AMAZING!! Wine tasting was fun, balsamic vinegar and olive oils were delish! All areas were full of tourists, even at the enof October, which took away from the charm of each stop. Bus driver, Lucca was pretty amazing with the narrow streets and turns! Disappointed at not leaving on time at several stops due to those who are not punctual (tour guide too lenient and did not stick to rules she set on leave times).

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